Is Gilt for me if I can't dress myself?

I'm a guy.  I'm not a metrosexual or a fashionisto--just a pretty average dude who plays sports, occasionally doesn't match, and can't figure out why anyone would pay over $100 for a pair of jeans.

I'm also an extremely casual guy--and would never dress up if I didn't have to.  T-shirts and jeans or shorts would be fine with me.  However, I do see the need to dress to impress once in a while, and it hasn't escaped my notice that on the rare occasion that I do put some effort into my clothing, it gets some non-zero attention from the opposite sex. 

So that's me. 

During Startup 2009, I had the occasion to meet Alexis Maybank, the founder of Gilt.  I followed up with her and asked her to lunch, since I think it's generally a good idea to get to know successful local entrepreneurs--and we also know a few people in common. 

I'll be totally honest--I didn't really expect a lot going in.  I couldn't imagine I'd have much to talk about with someone who started a high end fashion sales site--who could probably name more labels than I could name baseball players.  On the contrary, Alexis was awesome--extremely down to earth and very personable.  We had a great conversation and she was just as interested in what I was up to and the NYC startup scene in general as she was interested in talking about Gilt. 

We talked a lot about the way men shop (or try to avoid shopping) and how much of an opportunity there was in selling to men for the site.  It made a lot of sense to me--that guys want to get good value, but they also want to minimize time spent browsing.  They're also more likely to buy online because they don't run into the same sizing issues that women do.  In a way, Gilt almost seems more built around the way that men want to shop than women do--quick and efficient.

So I decided to try it out--and something hit me right away...

I have no idea what the hell I'm looking at.  You see, not being well versed in all these brands, I really can't tell whether what I'm buying is worth it.  They seem like good prices, but I really have no idea.

Actually, what's even more concerning to me are the associations that certain brands have.  As you get up the ladder in terms of brand hierarchy, I feel like most brands are associated with a certain kind of lifestyle--either intentionally or not.  We all know what it means (meant?) to be an "Abercrombie guy". 

Take for example, lobster pants.  Now, I didn't know what lobster pants were (thank God I don't hangout with anyone who wears them) until a friend of mind used them to describe a very special kind of douchebag. 

I didn't exactly need to be told about the association between lobster pants and douchebaggery to avoid wearing them--but what about associations that are not so obvious? 

Take this shirt for example:

What if, in the fashion world, it's universally known that John Varvatos is the shirt of choice for cokeheads?  I don't want to accidently wind up in the cokehead shirt just because I thought it looked cool.

Ok, all kidding aside, my main point here is that Gilt lacks the tools for anyone who isn't really into brands to make informed choices.  Interestingly enough, Amanda Peyton told me that she doesn't really know the brands either, but still loves Gilt because she implicitly trusts the site to pick out good stuff.  I wonder if men and women are different like that.  Guys don't hand over choices too easily... not without some kind of proof or more insight into the decision making. 

Compare that with the shopping experience at Fresh Direct.  I feel like Fresh Direct makes me a smarter food shopper.  It tells me what fruit is in season and which apples are for baking versus eating.  I'm a smarter food shopper because of Fresh Direct--and while I still want a simple and quick shopping experience, I think I might want a way on Gilt to reach out to the crowds and get a sense of whether these clothes are "me".  On top of that, some background on the designers or lables, some reviews of the lines, etc. might be helpful as well, otherwise I feel like I'm flying blind.  I think Gilt could use a bit of an editorial voice or some way to get to know the brands.

The bigger question, though, is whether it's part of Gilt's model to really care about me as a customer.  Maybe I'm just not the target market--and they're doing well enough with people who are more info fashion than I am.  I guess that would make it a lot like art that I didn't understand.  I had an ex that would tell me "Maybe it's not for you."