I don't think their aesthetic looks like the 90's at all.
http://www.supremenewyork.com/lookbooks
I went to their shop the first time I went to nyc in 96. Bought a t-shirt. That's the only supreme thing I ever owned.
I wonder what this 3-pack of Hanes perfect t's with a tiny supreme logo goes for. $9 just about anywhere without the 1.5" x 0.5" silk screen.
The 3 shirt pack is $24 which is pretty cheap compared to other companies "blank" tees. I know Analogs V-Neck packs go for $30 or so, Nike I could imagine for more, UO is like 2 for $30. So you're not really paying out of the ass too much.
The recent sky rocket in Supreme prices is horrible, mainly due to all these OF kids that want too look like Tyler the Creator. I sometimes feel embarrassed wearing Supreme solely on people trying to talk to me about OF when they see me wearing a Supreme tee.
I like the look of the company, yes, some of their ideas are clearly stolen, but good artists borrow while good artists steal. It's not really often do I see another company with similar looking clothes/designs and if I do, Supreme had done it first. The image of Supreme is very strong and attention grabbing and its a weird feeling of cool when you wear it, I don't know, I'm babbling. Overall, I think it wouldn't get so much hate, especially here on SLAP if it wasn't for the Hypebeasts that don't skate. Kinda like how bro's ruined DC for skaters, well DC ruined itself too but you know what I mean. Still though, awesome skaters like Koston, Olson, Dill, Spanky, Hsu, and etc rep the company and make it look cool and respectable. The brand also still makes decks/cruisers. Some of the skate aesthetic may seem gone, but it's in their roots and it's hard to keep that going for so long. I mean look, even some skate brands like DVS, Vans, Emerica, and etc are dwelling into the whole life style shoe game.
As for the high prices, t-shirts are usually $32-$38, which is steep for some. But going into any shop or Zumiez, you can pick up several shitty looking shirts that are priced as much. Hat's are a little more than what you see them going for, 5 panels and such are usually stapled at $44. Everything else is +$100 like jackets, jeans, sweaters, and button ups. I can vouch for all the fits on everything they make is some of the best money can buy. The talk of paying $300 for a 5 panel is all the sellers that stock up every season on Supreme, hold it for a couple months, and resale when it's not available through Supreme no more. That is not Supreme's fault.
Pretty much all I have to say about Supreme is you either love it or hate it. I love it, and I'm not afraid to skate in my $120 Supreme jeans, I get compliments out the ass on those and they fit/feel great to skate in. Supreme isn't for everyone, but in the end that's what makes it stand out to me.