Blacksocks.com: An infinite supply of black socks
crunchgear.com
crunchgear.com
http://shirt.woot.com is nice for T's at least but I don't think it would work well for anything more expensive or less expressive than that.
It's hard because people get fatter and skinnier all the time (usually just fatter) thus, the clothing "refill" doesn't work. Especially for pants. In fact, most men only bought new pants because of a size change, not because their old ones wore out. It works for socks because people's feet don't change.
Another problem is that even for men, standard sizes aren't standard at all. A size 32 waist pants from Old Navy is about a size 38 in Levi's 501. Athletic cut dress shirts are much larger than slim cut dress shirts in the exact same size. For women, you can multiply this situation by the number of retail stores and brands in the world. Sizes even change in the same line from season to season. Finally, people lie about their waist size, even to their computer.
When I decide that my old clothes are worn/stained/horribly unfashionable and set out to refresh the wardrobe a bit, I set out to buy a few new ones. After settling on which store to patronize (Am I too old for AE et al.? Am I too young for Brooks Brothers? Would I be just as happy with something from Target?), I go to that store. At that point, I browse around for a bit, get overwhelmed by the number of options, become unsure about what would look good (or even what's in style), and leave without buying anything.
I'd really like to see some sort of online or in-store system with a super-simple way of finding new clothes. Maybe three variables: age, desired style (hipster? MBA? stereotypical engineer?), and body type. The output could be something like, "OK, buy this, this, and that. You'll look good."
The 2nd part of your question, simply defining what style of clothing to wear is even more difficult and probably impossible to automate. However, there are professionals you can hire which will solve the problem for you. It's not cheap, but if you're single and make a good programming salary it may be a better investment than the latest digital camera or gaming system.
I've been fairly happy with the clothes I've bought by mail order though, there's been a few snags sure but you can send them back and it tends to be cheaper. I do go to the store sometimes, especially for jeans as it's hard to find pairs that fit me since I've got skinny long legs.
As for the skin color thing, I can honestly say that I have no idea whatsoever on how to judge that.
(Apologies to the grandparent if it's just me.)
Calf Socks - $10/pair
Knee Socks - $13/pair
Sneaker Socks - $10/pair
Silk Socks - $27/pair
Boxers 1st type - $45/pair
Boxers 2nd type - $39/pair
Briefs 1st type - $32/pair
Briefs 2nd type - $24/pair
Tshirts 1st type - $47/pair
Tshirts 2nd type - $55/pairThis is why this sort of thing would never work for me...My routine when I get home is:
Come in the door, pet the dog. Set the laptop down on the table, grab a beer from the refrigerator, walk out to the back yard, sit on the patio, kick my socks off, and start playing fetch with the dog. My socks end up in a pile on the patio and end up getting thrown away. If this place was 7 socks for 7 dollars delivered weekly I would sign up today.
It is tough to justify the cost for this, especially when i can go to walmart and get ~10 pairs of black socks for $4.
Maybe this is not aimed at nerds? (I'm thinking not).
Cool idea though. I'm with the person below here that says they get their shirts from woot. So do I. Woot is so amazingly perfect, I wish they did dress clothes as well...there are no choices to make, yes, or no. That is it. You say yes and you have a shirt at your door (or in my case, my office) the next day.