There's no better pleasure than putting a good beatdown on some dude who dresses like he's on the pro tour. The bigger the bag, the more dri fit he's wearing, the more everything matches, the more I'm motivated to really win big. Not sure why, but its just a guilty pleasure.
I can relate. I bought some $15 Ashburys from Steve & Barry's to parry vs. the country club types in their $120 Babolat shoes on the Har-Tru. That said, the cheaper shoes worry me regarding support, fit and cushioning. I don't wear them on hard courts. My ASICS's are vastly superior (and cost it).
I have acquired a wide range of tennis ensembles this past couple of years, from tournament t-shirts to Starter (Wal-Mart) to Fila. I vote with the better dressed camp. You're dreaming if you think anything from the big box stores is the equal of Fila or even Nike (I don't do much Adidas lately) in terms of materials, design, workmanship, or fit. I do have a $6 wicking t-shirt I got from Wal-Mart that I like pretty well. Some of the Champion stuff I got at Target is pretty nice too, but my favorite 1/2-zip from them is prematurely falling apart.
I think an analogy from the music world applies. You can make great sounds with some $300 guitars. A $2000 guitar will probably sound better, but if you show up with one, you'd better have some chops. Also, the really good tennis clothes can be very expensive and hard to find.
Here is an article I just came across on tennis fashions from a couple of years ago: http://www.nytimes.com/2006/08/28/sports/tennis/28fashion.html?_r=1&oref=slogin
It's from the New York Times. Is this an error: "In the 1970’s, Chris Evert ushered in an era of girlishness with her cut-out dresses, pleated Ellesse skirts, ruffled bloomers, blown-out hairdos and on-court diamond bangle." Technically, this is incorrect, as Evert didn't sign with Ellesse until 1980, right?
Just my two cents. ..