I have been known by friends/acquaintances to almost never wear a shirt without a collar. I've been complimented on my style a lot. Girls used to ask me for style tips...
I can't say it's really helped my dating life...if you don't have the skills to capitalize on it, it won't matter if 10 chicks say you dress great everyday.
#1) Nice shoes. Get a color that goes with your shirts, or your jeans, or your belt. Be different...for example, I don't care if Vans are popular, who cares. I think Vans are ugly as ****.
#2) Get clothes in a sizes that actually fits. This makes a big difference.
#3) A nice leather belt. And NICE jeans.
#4) Be different. Wear something that you don't see everyone else wearing. I don't dress outlandish...I'd say I'm pretty normal, but just different. My styles is a mix between thuggish/preppy. Sort of like Kanye West.
#5) Get clothes with a nice color that complements your complexion. I have dark hair, so navy blue and black goes well...I also wear darks/lights...for example, a black sports coat/blazer over a white T with dark jeans and white sneakers.
You don't have to spend a fortune either. Go to the store, try stuff on...figure out your size and then buy it on eBay. Check out thrift stores too, they rock.
Lastly, I think I also need to change up my style a bit. I'm not as "styled" as I used to be. I don't have all the accessories and junk that most guys have. I don't have a watch, or any wristbands. I don't have a hat. I don't style my hair. I don't have earrings. I do have a finger ring and a necklace. I also wear white Ts under my collared shirts. Someone else also mentioned "layering."
And I just have to add...dressing nice and getting compliments is not all it's cracked up to be. I think it hurt my confidence over time more than it helped. I became more dependent on getting compliments from girls to boost my self-esteem/ego that I found myself spending more time primping myself than most girls.
Also, when you "dress to impress" problems can arise. People will think you're too good for them, or that you're arrogant / full of yourself. Sure, you can get your way with looks, but when you walk into a room and draw stares people expect you to live up to a certain image when you open your mouth. At least that's the way I've felt about it. I stopped dressing really nice everywhere because I'd rather not be in the spotlight everywhere I go. Sometimes you just want to be able to blend into the crowd and go unnoticed. Just some thoughts that maybe you should consider...
Like how mpimpin said he gets compliments everyday...I did too, but at some point it gets distracting and bothersome to be honest.