Years ago in HS, my friends and I gravitated towards eachother with a lot of similar cultural background (similar social class, neighborhoods, school activities, etc) so we all started out looking a lot like eachother. Usual fair was Hollister with a bit of GAP thrown in for a more "traditional" side of it. All steered clear of obnoxious branding either way, so the biggest cardinal sin was the little seagull logo on our button ups.
As we all hit college together, a lot of us parted ways sartorially. Neutrals became the big thing, and a lot of the more bright colors we had embraced in HS disappeared, giving way to black, white, and grey. One went the way of the "classy" hipster, so to speak, with a decent looking blend of H+M with some classic Americana sort of influence. Another embraced a slightly more "geek rock" inspired image. One went a bit more sporty (and I mean sporty by Air Force 1s and tall tees), and my best friend frankly just went to hell (cargo shorts and a white tee with flipflops everywhere, no matter what the season).
I've managed to share my SF-learnings with the last one. He's become a computer geek and will easily throw down 2 grand on Apple products every 6 months, so he's accepted he has no room to criticize me when a new package arrives from BiG. I've tried to get him a bit more concerned about his appearance, and have even let him "test drive" some of my nicer denims (convenience of being about the same build). He tells me he can notice a legitimate difference when he wears my stuff as opposed to the things his Dad will stock his closet with - ex. running to my house and saying he has to be a funeral in an hour and if he can borrow a suit, or this summer I left a pair of PBJs with him to wear in a bit while I broke in a new pair of raws on my internship. But he still can't "bring himself" to pay for the stuff I get.
My wife takes care of herself, and has a lot of things that fit really well. She's not one to buy into any specific brand though, which is nice for our checkbook.