I can relate to this a bit as I have friends who would swear by the same thing; that if I want to meet a girl that actually has class, has her head on straight, is successful, she likely has money and you need to project yourself as successful - clothing being the quickest indicator. I do realize that these same friends are the kinds of NT's who have the same general problem most aspies do, they can't seem to will anything they want into existence relationshipwise, so they'll reach if they have to.
On one hand I'm already very picky about what I'll wear, most of the clothes I have aren't good enough in appearance by my own standards (and yes, that's probably more of a 'me' assessment not a broader reality), and I'd imagine that if I had to give myself a class lapel - if given the choice between buying an oversized house and just keeping it empty, buying a luxury/sport coupe that I could barely pay the payment and insurance on, or spending $1500 to $2,000 on wardrobe a year - the later seems the least absurd of the three. Then again I tend to take good care of my clothing as it is. I have two pairs of RE:VERB pants that I got from D.E.M.O. probably 4 years ago and they're still in great shape. Supposedly $200 pants don't last 3 times longer than $60 ones but still, if properly taken care of I can see where it takes a bit of the shock out of the picture.
Point being: if you do decide to spend that much on clothing, go with classics rather than fashion fads. If you think about dropping a couple C-notes on something and realize that within a year you could be embarassed to wear it; don't bother. Go with what'll still work and come off as classy in another 5 or 6 years.