I'm 34 and I have been gradually coming to the realization that I can no longer dress like it's 1996 and I work at a local coffee shop, which is just my day job: I play bass in a band called "The Fragile Elements." Have you read our zine? (Note: this is me from an alternate reality in which I was born in 1969 and lived in Austin) Nor can I dress like a guy whose wardrobe is selected based on roughly equal parts frugality, laziness, cluelessness, love of Aloha shirts, and contempt for what "society" says is "appropriate" and "matches." Fuckers.
I can dress up professionally if I have to: a job interview means the one suit I own that fits me and was not made before I was born. I also know basic slacks, dress shirt, and tie. With guidance from people who believe in that scam they call the "color wheel", I can even match.
I realize you can't give any real advice without a picture of me, which I'm not totally comfortable sharing right now, but I'm medium height and of slender build, bordering on comically skinny. What I'm looking for is a look that says "adult" but that still let's me project my own non-conformity. I really like that look that's become popular of retro-50s styles and hairdos, accompanied by tats and piercings. I've mostly just seen it on women though; are there some ways I could translate it to dude-wear? The two biggest constraints I'm facing are that it needs to be inexpensive (I'm on a very tight budget at the moment and for the foreseeable future) and simple to maintain (not a bunch of hand-wash, dry-clean, transport to the fountains of Xanadu where mysteriously beautiful women will lovingly cleanse it of all filth only garments).
I realize I'm not giving much to go on, but if the hivemind has some general pointers for this aspect of adulting, help me out here.