Me: No it doesn't. (Yes it does, but I have no idea what to do.)

Girlfriend: There are some great sales at the mall. (I'll appeal to his sense of financial responsibility.)

Me: I'm too busy right now. (I really am busy and I hate going to the mall.)

Girlfriend: You would look so much better in a palette more suited to you. It seems such a waste to not take advantage of your dark eyes and olive complexion. (I'll appeal to his vanity.)

Me: Wait, what? Dark eyes? Olive complexion? (She may be on to something.)

Girlfriend: Everyone thought you looked so cute in that shirt I got you last month. And the haircut, too. All my girlfriends thought you were so hot. (This works on ALL men...)

Me: No they didn't. (Hmmm...her girlfriends think I'm hot? Whoa.)

Girlfriend: And you can't go to that party in the same jeans and t-shirt again. Every picture of you on Facebook is in the same outfit. Potential investors might think you're a flake. (Threaten his start-up; threaten his baby.)

Me: OK, OK. (Good point, I keep hashing to the same frame.)

Girlfriend: I'll get dressed. You get the car. We can stop for a couple of drinks to celebrate on the way home. I'll probably love how you look. (Moving in for the kill...)

Me: This is so superficial, but you win. (Thank you, thank you, thank you.)

There are still some experiences that just can't be duplicated on-line.

http://www.jwz.org/doc/groupware.html

Unfortunately, when everybody else went off and learned this arcane system I was apparently playing Battletech. Now I know that large pulse lasers followed by SRMs (order very much dependent) is generally strong play, and everybody else knows that striped blue and white doesn't go with ... I have no clue what it doesn't go with, but it doesn't go with something. A lot of somethings, apparently.

It shouldn't be that hard to snap a photo of an item in my closet, play "20 questions" to classify it, and put it in a DB. Then every day, when I wake up, the app generates an outfit (I don't know, maybe a genetic algorithm would work for this, it is probably straightforward constraint satisfaction) and tells me "March 25th: Patrick, get these three things out. Can't find one? Click 'Backup Plan'."

Since there are a relatively prime number of shirts vs pants, every possible combination eventually occurs.

But this works for me. I don't actually Want to look cool; I'm perversely proud of NOT participating in all that superficial stuff.

So now the target market narrows.

Also, taking pride in how you present yourself is no more shallow than taking pride in refusing to present yourself well. You're still proud of your appearance. It's just hipsterism in reverse. If anything, being proud of inaction is more superficial, because you're literally congratulating yourself for doing nothing — it's merely an identity with no action to back it up, but you still feel superior about it.

And when I spend my free time on supporting a youth group, that's actually as shallow as spending it shopping for a cool outfit? Really?

I'm not suggesting you focus on it, but ignore it completely and utterly at your own peril.

>I don't actually want to look cool

Why? What possible utility could you be gaining by looking worse? Perverse pride sounds more like a ex post rationalization than a real reason.

I spend my time supporting a youth group; mentoring a high school game design club; gardening. What possible utility do you gain by ignoring these things?

Whenever I try something new, I have trouble knowing if it "goes well together" without some sort of outside confirmation. I've learned some basic tenets of what things "go with" other things, but I still don't branch out of that because of this problem.

Populating your library would take some effort, but it would be worth it.

Now couple this with another app/function that inventories your kitchen and lets you know what you can make for dinner and you've got a full blown bachelorator app.

Seems obsessive but I think there's a use for everyday folks. Although opening the closet door and looking at your clothes is pretty much the same thing.

It's fine for a shop, but bad for something aimed at dressing people properly and teaching them how to do so themselves.

Unfortunately, due to the differences in sizing between manufacturers, you'd probably have to be commissioning your own products for this to work, but it would be very cool for an off-the-peg suit shop, medium-high end lifestyle catalog (Land's End, etc) or something similar.

You may need fitting guides to show people how particular pieces of clothing should fit (trouser crease should break just above the shoe, shoulders should fit without bulging or sagging...) For bonus points, produce them with several different models with different body sizes - for me, having a heavier guy modelling a suit and showing how well it can disguise a gut would be a major selling point :)

Shoes, speaking personally, would be a total non-starter online. I seem to have narrower heels than many; I'll routinely find myself searching styles to find the ones that fit me properly there rather than slipping, even if they're right elsewhere. I'm sure some others will be a little wide acrosss the toes and need just the right level of bulging across the front, or a different arch height that makes positioning of the insole's mound under the bridge or the tongue important for their comfort.

tl;dr: I can't always just buy a certain size and know that will be right. If your business model is dependent on that being possible, it won't work for me and I doubt I'm unique.

Perhaps what we just need is rapid prototyping for clothes: "I'd like one like this, but with a more generous waist". Like bespoke tailoring but cheap and quick.

Agreed. It's not something I've done very often, but (for example) when you notice that the same trousers in two different waist sizes has different leg lengths in spite of what the tickets say, it's worth checking another pair sometimes.

Short of inputting your detailed measurements, I wonder how a site can solve that.

I once tried comparing official clothing measurements from various vendors online and came to the conclusion that they were all lying. Short of 3D scanning or painstaking measurement by hand, there isn't an easy solution. It certainly seems like a problem ripe for the picking.

Wow, someone please come forward with the name of this startup. I need new shoes, and if this works I'm spreading the news to everyone I know.

They're just at demo stage at the moment. They eventually want to integrate this into your outlet's website.

Also sucks that for all my fits, it always showed an Asics product, a brand which I personally don't like as their fits / soles are the worst for me.

http;//shoefitr.com/

It would be really cool to hack a Kinect (or more likely, several Kinects) into doing something like that for clothing.

And that, IMHO, is what you should be targeting - not the fact that men hate to shop but that most don't have the confidence to refine their own personal style...

Geeks/men aren't slobs and we don't always hate to shop.

Just to add more context so this doesn't come across as quite so snarky: I'm only validating the OP's concept that men hate to shop and offering that as a counterpoint to Ixiaus's suggestion that "the premise that men hate to shop is quite false." I'm a man. I hate to shop. I know many others who do, and many who don't. The OP addressed that in his post quite well.

In fact, I actually like looking good. I'm not a slob and I don't generally dress like one. The problem is that shopping is annoying. I don't have much fashion sense, I can't stand trying to pick a nice shirt out of hundreds of options with a half dozen variables each, and I never am able to tell what actually would look good on me.

A tool that did all the math and picking for me would be great. It's almost like a replacement for a spouse or mom that does the shopping for me.

Ideally, I would like all people in the latter category to stop caring about choices of clothing as a factor, but that won't happen any time soon, and meanwhile I choose to put up with the way the world works by acting accordingly to get the result I want. Ideally, I want to spend a minimal amount of effort achieving both of those goals, so I can spend time hacking on something useful.

So, I'd welcome anything which helps me put less thought into the the myriad incompatible standards for "fit" and other factors that determine comfort, and less thought into the myriad unwritten rules that form the collective expectations of shallow people ("fashion").

It's like going to Fry's and shopping for components to build a new computer - why do you think most contemporary non-geeks say, often, that they "hate shopping for computer parts"?

I would like all people in the latter category to stop caring about choices of clothing as a factor

I'm surprised you would say that - you may begin to notice that humans aren't computers with predictable API's to interact with. Inter-human communication and interactions are largely driven by sexual (perceivable or not) and biological queues. Smart and attractive (if you can dress well and take care of your body, you will be attractive) is an extremely powerful combination because the ultimate fate of humanity rests in the hands of our intelligence and a lot of the world will acknowledge you for your intelligence but if you want to make a serious difference - putting yourself together in a way that many non-geeks can relate with is crucially important.

Oh and clothing was never actually made to fit your particular body style - it's meant to be generic, you gotta get that stuff tailored! It's like custom fitting a computer for your needs, you have to do the same thing with your clothes, your body.

I once had the outlook you do, why do people like "clean" and attractive people so much? Why don't they see my intelligence more? On and on and on...

Do I like intelligence? Greatly so, I get along really well with many women who are lawyers, doctors, &c... because those professions seem to attract really smart people that also like to be attractive when they go out casually. This is not typically the case for women and men in technology - it's actually refreshing to meet someone that is both a brilliant programmer/mathematician/engineer and cares about their outward presentation.

I think the trick, though, is making sure that you can align style with your customer. When i first saw trunkclub i thought "netflix for clothes" which is a pretty novel concept if you figure that reselling overstock, late season purchases ala http://gilt.com/ is a pretty solid concept but if you also add-in the whole "personalized wardrobe" aspect, then it's really something exciting for folks that want nice wardrobe standards similar to what jesse at http://putthison.com/ advocates but don't need it this season.

"Dress Me" is kind of immasculating/infantilizing, whereas Trunk Club is kind of exclusive and sort of has an old world sophistication to it, both in use of throwback terminology "trunk" and the fact that clubs are such "guy things."

Not really comparing the feasibility of one business or the other, just pointing out my reaction to the identities...

Having a personal shopper is appealing I think. That being said, their brands are definitely on the higher end and more than what I'd probably be willing to spend on clothes. E.G. Denim ranging from $165 - $225 means a single outfit could get pretty expensive quick.

Still, I can definitely see the high end of the market being viable though. Seems like demand would exist at mid-market prices though too.

Dress.me sounds like a better execution for my preferences - I need a new shirt and some new jeans, so I go to the website and it finds exactly the right items for me with minimal effort or decision making on my part.

Also, your idea would require used clothing to be laundered and shipped out to other customers. There's probably room for an online Goodwill, but that's literally what it would have to be.

Good luck, and it sounds like a great idea if you can make it work!

And actually, I LOVE to shop. I just have no taste for clothes. I wouldn't know how to define my style. I need help.

I don't know many guys who like to shop (the second meaning) for clothing, but don't mind purchasing them (going in to a store, finding the item, paying for it, then leaving).

I'm still waiting for a gizmo that does a 3d scan of me and automagically finds the best fitting clothes, shoes, etc online :)

Shopping vs. Browsing, then would be more fitting?

When she goes out 'shopping', it defines a hobby, whereas it defines an concrete action for men. At least I guess :) (please don't call me macho !)

1. Looking at photos is not the same as looking at the real thing;

2. Clothes are more than just the look. How they feel is also important;

3. You obviously can't try clothes on online. You can (and really need to) in a store. I have clothes that fit ranging from M to XL depending on the brand and style.

So there are those barriers to overcome. There are additional issues.

First, I read the dress.me blurb and it says that when you signup it asks you several "this or that" questions. A theoretically reasonable approach but one doomed to failure.

The reason is that people (men in particular) don't know what suits them. When someone says they like something, it means they're accustomed to it. This is a key point service providers like this need to understand.

It's why you see people seemingly trapped 10, 20, 30+ years ago with their haircuts, shoes and clothes. Typically this is how they looked and what they wore when they were teenagers and in their 20s. That sort of thing sticks because it's what they knew growing up (much like musical tastes tend to be) or even it's just the nostalgic angle: that style takes them back to probably what were more easygoing days.

Second, there are an awful lot of men--we geeks are particularly guilty of this--who have a completely utilitarian view to pretty much everything, including clothes. There's a reason the programmer stereotype is t-shirts and jeans. These clothes are comfortable, require very little maintenance, are cheap and require very little thought.

Clothes, like many things, are a statement about who you are as a person. Pretty much everything we do is some form of expression of who we are. This is even true of things like programming language choice.

So the problem we geeks have in particular is that we don't generally care about what kind of statement our clothes make, which in and of itself is a statement.

Anyway, watch any of the makeover shows that are on TV. Whether they be for men or women you will see the first thing the self-appointed style gurus will do is beat them out of their old habits into things that actually suit them. Asking them what they like would get you nowhere.

This is also why the cliche exists of women shopping for men. I think women are probably more naturally inclined to the "group" aspect of pretty much all forms of self-expression, clothes being just one. Just watch a woman--particularly a young woman--get dressed for anything and you'll quickly realize it's a group not a solo activity deciding what to wear.

Sites like this I think are seductive to those who start them, much like dating sites are. It seems like it should be easy, right? I think the reality has proven and will continue to prove otherwise, at least until these fundamental problems are somehow addressed.

The true meaning of "I hate shopping" is more likely to be "I hate making decisions about things I don't know about, care about or both." The "knowing" part can probably be fixed. The "caring" part is a much bigger problem.

You have a "style expert" who you meet with over Skype video. They send you a box of clothes to try on and review with your expert over Skype video. Any items you don't like or don't fit you put back in the box and send back. They include the return shipping label in the box so you just have to put the label on tape up the box and have FedEx pick it up. You only pay for the items you keep (no shipping charges or extra fees). They try to make the process as painless as possible.

Over time as you meet with your style expert, it's always the same person, and get to know each other they get a better sense for what you like and don't like as well as keeping track of things such as sizes and fits. They also recommend what things work well together so you know what things to wear together, etc. They have definitely pushed me out of my t-shirt and jeans comfort zone, without going to fashionista or anything.

The primary drawback is my clothes budget is definitely higher than it use to be, as most of the clothes are significantly more expensive (no $20 dollar jeans) as they tend to come from more boutique and small manufacturers.

While that probably sounds an awful lot like an advertisement I have no connection with Hendricks Park other than as a happy customer.

Seems like others might be drawn to this if they didn't have to shell out $200 for a pair of jeans each time. I definitely get the desire for premiere clothing/shopping just wondering if it can scale down the price line and still work.

Two things that stand out and (deliberately) separate this site from the casual online shop experience:

"Hendricks Park is a _luxury clothing_ service for men who have better things to do with their time than shop for clothing."

"Men who enjoy and value our service the most, tend to buy at least $1,250 in clothing per season."

Specifically, should a man using this service budget $5,000 a year for clothing?

Thanks for the rad feedback. I appreciate it. It'll make my product a lot better.

You're right, shopping online is different. But despite this, shopping online is a billion dollar industry that doesn't show any signs of being slowed down simply because it isn't taking place in person. I think if women (who, arguably, are more obsessed with fit/feel/etc. than guys) can shop online then there's definitely a way to make it work for men. That's what I plan on doing.

Also, great point about clothing serving as a symbol or a form of self-expression. I think you're spot-on about programmer types making the statement, "I don't really care about clothes," but a) it assumes everyone is making the same statement, which is problematic (we can't ALL have the same message to express since we have such a diversity of experiences in how we perceive the world) and b) it eliminates the possibility that a typical geeky dude never wants to look good, which I would argue isn't the case.

Nevertheless, great points and I appreciate them all.

Buying something online really lacks any information on how the clothes will fit. There's basically that old saying and I don't see how it can be solved when buying online "wear the suit, don't let the suit wear you." If you could get the site set up to find locations near the user where these suggested clothes can be tried on/purchased then I think the site could be very useful.

As it is I was already interested enough to try to go to dress.me and sign up (only to find out it doesn't exist yet), however I wouldn't be willing to pay for it. If I could get a discount on the clothes the site suggested by being a paying member, then I may be willing to pay for it (but then it comes back to the conundrum I've already mentioned).

I only have one piece of constructive feedback, which I hope you will pay some heed: Men have fragile egos. You should be wary of saying "Because guys hate shopping" or suggesting in any way that men do not have a sense of style. Yes, many (maybe even most) guys do not have any sense of style, or might hate the whole shopping experience. But I guarantee that using this sort of language as your tag-line (or 30-second elevator pitch) will turn away just as many guys from your site as it catches.

My suggestion is that you simply tout the benefits of this suggestion-based shopping. It's an obviously great idea, which I am backing 100%. Sell them on the benefits without making claims which will hurt their egos.

However, this can and should be bundled with a more assertive counseling activity: "we're not going to force anything down your throat; however, if you're not satisfied with the way you're perceived, and you think your clothing style is part of the problem, we might have some suggestion to offer".

Counselling should itself be structured in two levels:

* generic help for free ("If you have $PHYSICAL_FEATURE and want to be perceived as more $QUALITY, you should chose clothes which have $CRITERION. Beware that $CONTRAINDICATION". Could be raw text with a couple of diagrams, could be something more interactive)

* referral to one-to-one counselors, with a commission on their fee.

However, it sounds like a real problem, with real solutions to be provided, to people willing to pay for it (nobody expects to get clothes for free, no freemium competitor will undercut you), and with enough diversification possibilities to find one successful way to grow. As always, and especially for very personal services, flawless execution matters much more than the initial idea.

You'd say the same thing about jewelry (BlueNile.com: 58M quarterly revenue) and shoes (Zappos.com: bought by Amazon for ~$1B).

(note: I edited this to say "jewelry" instead of "diamonds")- I agree loose diamonds are a commodity. An wedding ring you're going to wear the rest of your life is something I'd imagine people would want to see/wear before buying)

I don't think that's the barrier for clothes.

Shoes are a closer analogy. I would be very interested in seeing an answer to this question to those who buy/bought from Zappos:

When you buy shoes from Zappos, are you buying a style or shoe that you've previously tried on or bought?

Also, I think women's shoes are a different market to men's shoes. Women I think almost take it for granted that shoes, particularly dress/fashionable shoes, will be uncomfortable.

Again I take a utilitarian view to shoes. I have a hard time finding a pair that fits nicely. I'll buy lightweight runners/sneakers/joggers (depending on your lexicon) and then wear them virtually every day until they fall apart and I buy a new pair.

I imagine I am not alone in this.

In particular, it cannot be overstated how important a good return policy is. It's also bizarre how many companies get it wrong.

Example: I bought some stuff from Bed, Bath and Beyond a month or two ago. I realized I'd gotten the wrong thing. By this time I'd misplaced the receipt. I was expecting a hassle when I went back to the store. I walk up to the service counter and ask what the return policy is. The women behind the counter says they have a no hassle return policy.

She said she could give me store credit no problem or, if I preferred, she could look up the receipt on the system with my credit card. If she could find it, she'd give me a refund instead. She did in fact find it. I didn't have to produce any annoying pieces of paper nor justify why I was returning the item.

After that incident I went and spent another $150 in comfort knowing that if what I bought didn't work out I could return it.

So my advice for anyone dealing with physical goods: make it as easy as possible to return goods and customers will spend more. Make them love your store/website/whatever.

Online clothing stores need an innovation like this.

My girlfriend (and me to a certain extent) generally returns around 50% of her ASOS purchases after trying them on at home. You can return them in the same bag, have them picked up or drop them to any Collect Plus (http://www.collectplus.co.uk) location.

The delivery is fast. The prices are ok. So far I have never returned my shoes. They all fit perfectly and customer service is great!

But you need an expert, I don't think this is solvable on line.

[1] http://www.truthaboutdiamonds.com/truth-about/james-allen-bl...

"Have You Ever Tried to Sell a Diamond?" is also interesting reading. http://www.theatlantic.com/magazine/print/1982/02/have-you-e...

Shoes are slightly different than clothes. While fits do vary slightly, it's not even remotely close to the variations in clothing. Online shoe shopping also produces better results than clothing. Things like feel aren't are varied either and the details are not nearly as important. I wouldn't buy expensive shoes online, but for most types of shoes, I much prefer online vs. b&m. Partially because of variety and partly because of my size (13 US).

Contrast this to my online clothes shopping habits, where probably at least 50% of my purchases are returned.

Compound this with the total lack of quality control in garment manufacture and you begin to see why shopping is such an ordeal. The same brand and fit (model?) of pants from Dockers, Levis or the Gap will fit you differently, depending on the color of the fabric. Typically, the darker the color of the garment, the more snug the fit. Sounds ridiculous, right? Lighter fabrics tend to relax out more. It's all about the fabric content. Raise your hand if you've ever washed something and had it either get smaller or bigger, or become completely misshapen. Quality control is done on the first hundred or so garments that come out of the factory. After that, it's a free-for-all.

People don't know what suits them because there is a very real learning curve to the whole process of getting yourself dressed. This is why most women shop and dress in groups. Institutional knowledge is hugely valuable. So is a cloth tape measure.

I watch What Not To Wear. They make it look easy. Then they make it look hard (the "victim" almost always cries). Because drama sells. But behind the scenes is an entire staff of people who follow fashion trends, understand a great deal about ready to wear garments and know where to go and what it costs. That's a full time job. Nobody has that kind of time, and it's a barrier to entry.

Not caring about what kind of statement our clothes make is a learned behavior. The fashion industry does not care about the happiness of the customer. If you don't believe me, find a girl who won't slap you for it and ask her about her bra. So if they don't care, why should we?

This saves me time in the store and also makes the decision less agonizing since I can make it over a few days.

So, yeah, you're probably dead on about how 'wrong fit' can be interpreted.

IRL, you get people who miss their measurement unit (cm or inches seem to be complicated). Or they misunderstand instructions and thus just enter 10 cm while they should enter 10.5 cm.

However, there are online stores for custom made shirts (with lots of measurements) and it sometimes works, depending on the dedication on the user's side.

Also, try doing the first few shirts individually (typically there are discounts for buying 4-5 at a time). You may need to have 1-2 great-but-not-perfect shirts first. But once you nail the measurement, it's easy from there on out.

Believe this: tailors aren't just for fancy clothes and they aren't expensive. I take all of my jeans to my tailor and have them hemmed to the exact length of my legs because not a single clothing manufacturer makes clothing that fits my length!

http://www.esquire.com/blogs/mens-fashion/pants-size-chart-0...

So it doesn't surprise me that there's "vanity sizing" in men's trousers. Not even a little bit. This, too, makes for a tough call when it comes to getting dressed. Camel toe or saggy butt? Hm.

(eta: sorry for devolving this discussion into a rant on ready to wear clothing)

Anecdotal point, I bought a pair of black jeans from the Gap (4 months ago), having tried on several other colors of the same model (size/cut), each fitting different. Since I could not find an identical fitting pair in another color, I decided to get a second pair of black jeans (exact same).

Being paranoid, I decided to try on the second pair before purchasing, and it fit differently than the first.

I decided to try on the first pair again to make sure I was not going crazy. Exact same pants, exact same UPC, different fit.

If I can find a good piece of clothing that fits me well, I tend to purchase several of them at once (in the same exact color/style).

Most online clothes shops I've seen have a really good return policy and free postage. They encourage you to order more then you need, and as well different sizes. So you effectively get sent a whole bunch of stuff to try. You try it on, keep what you like and send the rest back for a refund. It's even better when you're ordering online from shops that have a physical presence as you can just take it back to the store and get a refund instantly.

Nothing to try, nothing to see, just buy and wear.

Oh, and Hanes tagless white t-shirts XL

Oh, and Nike slippers 10'

That's my basic outfit 24/7 and I can buy it all online.

They were able to base their successful decisions on that assumption. Like using same-day shipping. Sending multiple clothes for the price of one to allow them to use the one that fits both them and the occasion. And more recently, including any accessories that can go with their choices.

I think some of these ideas can be generalized. As a shopping service, you can overcome all three barriers by sending multiple clothes based on the "this or that" questions. Or current trends. Or a both. This allows the buyer to make their final decisions within the comfort of their own homes. They can then send back all but the clothes they keep, if any.

I'm pretty certain men won't use this service for renting (though what do I know, I haven't tested this assumption), but treating it as such, you anticipate returns to be normal. The service can possibly learn what works for recurring customers (what fits, what general style they keep, etc), and lower the return rate. Furthermore, it can find trends in the "this or that" questions vs return rate to better predict as to what will be kept. It can even make fashion suggestions and educate on the subject via email/blog. I think us geeks would be more open to fashion advice if there were theory and stats to back it up (well, I would anyway; there's mountains of theory behind design, why not fashion?). Translate the emotional into the technical. Base suggestions on what both visually pleases the crowd and feels good to the indifferent individual.

Does this sound any more feasible?

Also, by asking the user to choose something he knows he's comfortable in, the website can get really interesting metrics to help determine the good size.

Finally, I guess it's always possible to give more detailed metrics of you (how much you weight, height, arms length, etc.). So, basically, it could be optional but if you're willing to spend a little time measuring it, it could be of a tremendous help. In fact, if I knew I could avoid big stores by taking a few measure of me, I'd do it right now.

People who are models generally fall within a certain range of sizes, but it's still impossible to predict perfectly what will fit them, and you might not even have all the sizes available.

What I would like to see is specific measurements of the garment. The distance from the collar to the bottom of the shirt, the width at the bottom of the shirt, the width of the arms, etc. The few standard measurements that are usually provided with a dress shirt or a pair of pants are a good start, but they aren't nearly enough to judge fit. I've had shirts custom made (via the internet) that use the reverse of this process, where I provide them all sorts of different measurements and they make the garment to fit. They all fit very well, so I have hope that making this information available could help with the fit problem.

The real question is whether there is a correlation between clothes and programming language choice. Do lisp users wear highly functional clothing that's really ugly to look at? :)

And they are simply always stylish, fit perfectly and you can hardly go wrong in them. Right? RIGHT???

Hence:

1 suit

3 proper shirts

3 pairs of jeans

10 black t-shirts

I've worked on http://styyler.com for some time (never finalized it), and we were inspired by the fashism.com, polyvore.com ($8M funding), chictopia.com, lookbook.nu, weardrobe.com (acquired by Like.com), chicisimo.com, ...

In the last year I managed to transform my wardrobe from jeans + threadless shirts to strictly dress clothes, but without looking conventional about it or spending a lot. It took some work initially, and some courage to try things out of my comfort zone, but now I dress well by default and it feels good!

First place I go is Value Village or another used clothing shop, maybe once every couple weeks. I don't spend more than 5 minutes (you learn to be efficient pretty quickly). I look at dress shirts, pants, jackets, and ties. Nothing else. I may not find anything, but I feel good when I do ($5-10/shirt, heck yes!). I've found several great shirts that would be $60+ new, and a couple really sweet blazers too.

Then I hit somewhere like Winners, reasonably stylish but not so expensive. When I find something I think I like, I ask myself a couple questions:

a) Does it look like a "dad" shirt/pant? b) Would a teenager wear it?

Both are deal-breakers. If I'm really unsure if it's too loud, I'll try it anyway. But be strict on fit. Dress shirts that look like a garbage bag wrapped around your waist are terrible. Of course, you have to tweak to your physical size, but you can find things that flatter. If it doesn't flatter, even if it's nice, put it back (even if it's "your size").

And for the first while, have a woman come with you, but tell her what you're going for. She'll steer you away from the truly awful, but encourage you to take a chance on the brilliant too :)

As one of the later, I have to say that actual shopping is a pain and if I didn't live in a little town replete with boutique attendants I probably wouldn't shop.

Most of my more successful hacker friends in the finance industry whose wives are not interested in shopping for them went this route, and rely completely on their personal shoppers. Even the ones I would consider only slightly better dressed than random selection love the service.

* Find a favorite pair of jeans, buy 3-4 pair, wear them every day.

* Find a favorite a t-shirt, but 4-5, wear them every day.

* Ask for socks for Christmas.

Solid colors are recommended because then you:

a) aren't a walking billboard and,

b) it isn't as noticeable that "wtf you wore that same slogan/whatever shirt two days ago".

It makes complete sense. I can't stand retail spaces, and honestly, even shopping every leap year is an insufferable, demoralising sink.

To "figure out what their style is" is really the missing link for me, and I'd probably pay for this alone. However, I at least have some interest in it, just because my brother is a complete 180 from me and is very into style/clothing.

One cautionary note, the target has to recognize the need for the service, which might make it a harder sell. Look at how hard it is to get people to do something about finances! It's simply a blind spot for many, in the same way style is. Those hate to shop folks don't see why we should care about it. What's the benefit?

If I was at all style conscious I'd be more inclined to focus on the opinions and suggestions feature, even though it seems like an afterthought to your feature set. People who 'get' style and the clueless would both benefit (and frankly, the in style people are going to be more passionate about it).

I do go shopping voluntarily when we need to buy a nice dress for my wife before going on a cruise vacation, etc. She likes to get something that I like.

Way back when I was single, I bought some clothes pushed on me by sales clerks that later friends mentioned didn't look so great on me. For single men, I would advise waiting until you have a girlfriend with good taste - then stock up using her advice.

Dress.me might work, but it seems like it would be difficult to do using only questions on a web site.

Maybe don't mention this plan on the first date though.

Besides, it shows that you're clued in. She will definitely recognize that you need new clothes before you do.

I don't think he got a single new article of clothing until we got engaged, when I started buying his clothes.

How would you know she has good taste?

I tend to grow my hair longer now than I used to, just so I can go to my hairdresser and say "You're the professional, you choose." Otherwise its way too easy to get stuck in a rut, and to be honest, the styles that GQ and Esquire show you usually require:

a) a bunch of money

b) a bunch of confidence that you look awesome and not a douche

c) a slender figure

Most guys aren't any of these things, so they'll buy a slightly too baggy T-shirt and a pair of jeans and call it a day. There could be much more.

- Every body type is different and every label has different sizes/cuts.

- how the outfit fits makes up 90% of an outfit looking great

- target market lacks the ability to judge fit for themselves

BTW, I'm not a fashion expert but I married one.

tldr: sartorially skillz are important

From my own shopping experience, I generally find one brand of shirt/pant/shoe that work well and then it's my go-to brand. Anytime I need to buy something new, that's where I go. I hardly deviate or try something new because as you mentioned, I hate shopping and as other people have mentioned, fit and feel are important.

However, I think you can expand your product by saying "hey, if you like Shirt A, then maybe you'll like Shirt B". After all, the style from one brand often remains the same and even guys will want different types of clothes for different events/moods/etc.

My one data point, FWIW.

The one area that I have most trouble with isn't types of clothes it's the color coordination. I've had hundreds of comments like "oh your shirt doesn't match." To me it looks perfectly find. Or one that's strange to me is "that color is not you." My answer is always, "I have a color?" but no one clarifies.

Or I'll buy a dress pants in one color, and have no idea what color I should buy for dress shirt and other stuff like coats or sweaters to match.

I imagine something like saying hey I have so and so pants what color or shirt best matches it?

Something that works with your exist wardrobe, or teaches you how to color coordinate would be great.

I'd think of it as being like those services where people go and put together a couple weeks' worth of meals: those people don't hate cooking, they hate the results when they fail at cooking. Personally, I enjoy when I find something that fits right and looks good, I just have no idea how to go about making that happen reproducibly.

Every month, you get an email with pics of 2-4 different ties. If you like one, you order it. If you don't, you don't order it.

It ties in with other peoples' comments regarding personal shoppers, but once you get past the initial mvp stage, I think there's an opening for adding the ability to ping my clothing-savvy (female) friends to say "what do you think of this?" There's possibly an exploitable network effect in there.

1. Kinect for sizing you

2. Clothes on your avatar

3. Done. You are now a gazillionaire. Of course, there's lots of next steps, like getting the Snoop collection, the slacker collection, the yadda yadda, but fundamentally, when you can get sizing automated by your Kinect and shop on your 360, the boys are happy.

I really wish I had some spare time to do this, because this would be fabulous. In fact, you wouldn't even need to get sized that often; you'd only have to do it once every so often. You could just open up the app, and throw fashion on your avatar.

I'm not sure if I would actually buy online, but asking me questions and presenting with an idea what to buy would be a great help. I tend to use the people working in the shop for this - since they usually wear the clothes available in the shop, I end up with "I want to buy the stuff you're wearing" (or some less creepy alternative) when I spot someone whose style is ok.

I'm assuming you're going to monetize by eventually becoming a reseller or acting as an associate of sites you link to (could be wrong). If not, then I would advise this route over charging outright for using your service, as I'd be far more likely to use it that way.

All that being said, I really look forward to your launch so I can try this out. I am exactly your target audience.

When you see a dominant hegemony (as in male-dominated technical startups), it's useful to imagine yourself as the minority and try to see what your hegemony is missing.

It's hard to put yourself outside your range of experience, but it's a useful exercise anyway.

If they had a way of matching your favourite clothes to others and making recommendations based on style and fit I think it could be great.

If the website included a little "3d model" of a person, customizable to make it my size so I can try on different clothes, that would be ideal.

I've been reading a lot lately about how the web is dominated by women, and that men shouldn't try and sell to women. That. In reverse.

Charging a monthly fee for access to the service, or a fee for each consultation? Some sort of referral fee or commission scheme for referring customer to the (eventual) brands and stores?

Go to GAP, straight to the jeans section, pick a 32/34 normal cut, pay, get the hell out. Done.

putthison.com selectism.com gq.com/style/style-guy asuitablewardrobe.dynend.com/

(1) Pictures. Now digital cameras are terrific, and so is the Internet for showing high resolution pictures. So, high resolution pictures. Lots of them.

(2) Measurements. When I shopped for clothes for my wife for Christmas, she wondered how I was able to buy her clothes that fit. Easy: In secret I went to her clothes closet, picked out some of her clothes I knew fit her well, spread them on the bed, drew a sketch, took out a tape measure and MEASURED everything relevant. At the store, I did the same. At a store, e.g., Talbots when they still had nice clothes for women, a sales woman came and asked me if she could help and what size I was looking for, I explained that in clothes, especially women's clothes, the stated sizes didn't mean anything and I would use a tape measure instead.

(3) Colors. Colors should just be specified in 24 bit RGB, period. Then at home given the RGB values, use some drawing program to put up a big patch of the relevant color and compare with such data for other items already have and the color pictures. Then can do well on color.

(4) Terminology. The rag trade needs to totall stuff it on their 'creative' names that are poorly defined to anyone and just meaningless to men. So, to say that a polo shirt is a 'pique' is nonsense. Instead, say "knit" and then describe, in clear, complete English sentences and close up photographs any more of interest.

I went shopping for blue jeans on-line at the site of one of the famous brands, saw about three dozen colors, each with some concocted color name -- maybe New England burgundy or some such -- and gave up. I wanted just standard blue jeans, and the color names were meaningless and the photographs were far too small to see the colors.

One more, the rag trade has to understand that on color, about 25% of men are partially red-green color blind.

Last, the rag trade has to give up on expecting men to buy clothes like women do. Men just ain't gonna do that.

So, long the idea has been to play on the propensity for women to 'fit in'. So, use some 'authority', say, 'designers' from Paris, Milan, NYC, etc. to specify the 'new look', fill the stores with such rags and little else, and try to get young women embarrassed to be see in anything else. And have a 'new look' each 'season'.

Some of the seasonal changes have lost a lot of their punch, but there's another, related idea: Young women are easily frustrated and dissatisfied. This is an old point, e.g,, illustrated by the two sisters in the original Disney 'Cinderella'. Thusly, frustrated, the women want a 'MAKEover' which consists (as in 'Cinderella') of just throwing 'out the old' and 'bringing in the new'. So, lots of good clothes are just thrown out. Huge waste. Men don't like that or do that.

For men, now, for nearly anything, including business, shirts -- polo or sport. Pants -- blue jeans. Shoes -- nearly anything comfortable, but actually running shoes are only for more casual situations or athletic situations.

If an when a suit is needed, it's easy: There are only three colors, black, navy, and dark gray. A pattern is okay as long as can't see it more than 2 feet away. Shoes -- black.

But the effort to get men to be 'fashion conscious' will never stop and, I hope, never succeed.

I always find it fascinating how sometimes ideas can go a long time untouched, but when someone finally decides to work on it, it seems like 20 other people had the same idea at once.

This or that questions wont help. You might ask: blue or white? I say depends; you might ask: smart or casual? I say depends.

There are no questions that can 'solve' my style preferences and even if they do, the items I buy will not always follow them (maybe found some really cool green shoes that go with my blue shirt, which I wouldn't have bought if I didn't already have the shirt). I like moccasins for summer and oxford shoes for winter, seasons vary.

Even if you can somehow compile a perfect profile, then how the hell are you going to find items that match it? Very few retailers list things such as colour, season and material separately in a manner they can be easily gathered.

I sincerely suggest you to look elsewhere.