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.