Menswear rant

I find it extremely hard to be a well dressed guy. Not because of monetary issues (well, maybe a little) but simply because I'm finding myself in an absurdly difficult time of my life fashion wise: I'm both a man and a boy, with a limited amount of money and plenty of insecurities. Also, I'm skinny. Let me explain.
Being in my late teens, I don't wanna dress in jeans and hoodies anymore. I'm past that, I want something more polished, more serious. However, I work at McDonald's and go out with my friends for drinks on the weekends, so wearing a suit wouldn't be exactly appropriate in any situation. And that's where my problems lie. Nowadays, menswear retail caters to young children, slightly older children, teenagers and adults. Nothing else. What am I, a young adult with a fair amount of maturity and personality, supposed to wear? I don't feel comfortable wearing a three-piece suit, but I also don't feel comfortable wearing bright yellow jeans and a pink hoodie. Where's the middle? And where can I buy it for an affordable price?
Yes, an affordable price. As said before, I work at McDonald's, which means I'm not exatcly rolling in cash. And, as Murphy's Law would have it, the only shops I know in Wellington that sell nice, perfectly fitting, fashionable-yet-not-trendy clothes happen to be the most expensive shops in the city. Maybe I have expensive taste, but that's not doing me any good.
And what about the places I can afford? Well, that's where I shop. Unfortunately. Don't get me wrong, I've found some pretty cool stuff at places like Cotton On and Jay Jays, but mostly what they offer is supposedly trendy (not good trendy, that kind of trendy that will make you embarressed to think you used to wear that in six months time), disposable clothing. Sure, I've got about three pairs of nice skinny jeans. But that's what they are. Nice. Not perfect, not fabulous, not amazing. Just nice. Same goes for most of my t-shirts, and maybe a couple of sweaters and a jacket. The rest is all stuff I'd never wear outside if I had an option, but somedays are just way too cold for me to, well, have an option.
But hey, I can't be that unlucky, right? I'm not the only 18 year old with a limited amount of cash in the world. Most guys seem to be doing just fine, right? Yes, right. But in my opinion, if a guy in my situation actually likes his clothes he either:
a. Doesn't care about fashion.
b. Lives in a fashion friendly city, like New York, where you can find pretty much anything in great prices.
c. Is more creative and/or smarter than me.
d. Some other reason I don't know. But wish I did.
So, for now I'm getting by. Wearing my pre-made combos (I have three: skinny jeans + t-shirt + oversized woolen sweater; skinny jeans + t-shirt + jacket; skinny jeans + t-shirt + cardigan. Oh, the variety) and struggling to find something new to buy. Maybe I should just lose my fear and start wearing stuff like harem pants, long wife-beaters and printed tuxedo jackets. At least I'd have the excuse of trying to be a hipster.