Originally Posted by wvuguy
Always good to connect with other Mountaineers !!! FWIW, I'm just outside Cincinnati; where do you live, goblin ????
I live in Cross Lanes and work in Charleston.
If you keep yourself in good shape and don't try to be something you're not, I don't see any reason why you'd "fail miserably" in the streetwear/casual department. I'm 35, and good basics like t-shirts, jeans, and sneakers are pretty much my entire casual wardrobe ... I avoid branding and logos like the plague, other than Chuck Taylors, and I make sure everything fits reasonably well. I can tell a definite difference between the way I dress and the way other lawyers my age dress when out of the office, and most people think I'm about 25, whereas most of the other lawyers my age look about 50. (This is not necessarily a good thing for me professionally, but works out just fine socially.) Except for my one pair of premium jeans, I spend a fraction of what they do on clothes.
I'm not saying avoid all personality in your style, far from it ... I fall pretty firmly into the ex-punk/skater camp - blank or band t-shirt, Nudie Regular Ralfs, and Chucks, with layers added and Docs instead of Chucks for winter. I've been wearing the same basic outfit, with fit differences, since like 1985, and I'm pretty sure I'll be able to wear it in 2015. But it's all fairly unobtrusive, almost "anti-fashion" stuff.
I wouldn't go out and get a Bape t-shirt, True Religion jeans, and those Timberlands with the giant tree unless you know for sure you want a certain look. Past a certain age, you may just look like a total fashion victim.
How do you dress now? How old are you? What do you like to do in your "off" time? What are you trying to accomplish with your style overhaul? Do you want to look younger, pull college tail like a tractor, etc.? I've got to warn you, if you're just looking to impress chicks, this is probably the worst place in the world to ask advice. Seriously.