Ok Windwork and everyone else who wants to improve their look, listen to me...
I was in your EXACT position a couple months ago. I started off looking for a new watch, then colonges, then shoes, then I just went ALL OUT recently and build up a completely new wardrobe($1000-$1500 spent).
If you want to get a better idea of what looks good on you, what colors work well together, what styles are good, etc.. What you need to do is go out shopping and try on as many different items of clothing as possible. Go to new stores you've never considered even entering before, try stuff you would normally never consider wearing and ask for the sales people's opinions!(This is important). Being inexperienced with what looks good and what doesn't, you're going to want to seek the opinion of as many sales associates, even customers, as you try on different things. This is especially important if you're trying on something you're not used to wearing. Ask the sales associates what they think would look good on you. Ask them stuff like "What would look good with this shirt/these pants?".. "Does this color go with that color?", "What colors work well with each other?", "What kind of belt would look good with this?" etc... Seek out opinions like a mad man. After doing this enough, in many stores, in many malls, you will eventually "get it"(good sense of style).
One of the styles that I find works extremely well is dressing GQ(button down shirt, designer jeans, sneakers/loafers, pendant, watch, belt).
When looking for a pendant, you may need to search through some women's stores as well. I found a couple of mine at Le Chateau(Canadian store, mostly for women).
As for the dress shirt, you MUST make sure it is form fitting and isn't too long in length. Getting this right is key to looking good. Especially the length part, most guys wear shirts which are too long for them. You also of course need a good body. Assuming you have that, find a dress shirt which is tapered and is not baggy through the length of the arms. When putting it on, you want to leave the top button(or 2) unbuttoned, and the bottom button unbuttoned(so your belt shows when hand/s are in pockets).
Assuming you found a shirt which fits well along the length of your arm, you can now roll up your sleves in some fashionable ways. One way is just to unbutton the front of the sleves and flip the cuffs back once. If its tight around your forearm, you'll only need to do this once. If its not tight, you can pull it up a little more(after its been flipped), and use the excess material at the front to roll overtop the cuffs(you can control cuff flare-out this way too). If the dress shirt fits well around your arms, the cuffs will flare out nicely, if the dress shirt is too baggy for you, you will end up looking stupid. Another way which is somewhat unique is to flip the cuff, then pull it all the way up your arm until the excess material below your cuff ends around your elbow. At this point, you roll that excess material over the cuff once or twice and adjust how the cuff flares out. You can even try bending the outer tips of the cuffs downwards. This will give you a unique short sleeved look.
For the pants, you're going to want to go for boot-cut jeans, girls love them. They come up high around the crotch, narrow around the mid leg, and flare out a bit at the bottom which also covers up laces well on sneakers. Here's an example of what kind of jeans I'm talking about:
http://www.le-chateau.com/products/index.asp?navLev=3&gen=2&NavId=24
There are also jeans which have a mesh like fade to them which look a bit better than these.
Add to this a nice pair of loafers:
ex:
http://www.walking-shoes.com/mm556.html
-Rockport Timor
or sneakers: (there are some nice sleek italian ones out there)
For the colder seasons, you will of course need to add a leather jacket to this. In the summer you can wear the jacket some nights, or right after it's rained. You're going to want a unique leather jacket. It's hard to find anything but the typical leather jackets you see year after year, so this part may not be easy. I found myself a nice biker jacket that looks like Vin Diesel's in Fast and the Furious...
Then add a watch, a ring/s, some shades and you're set!
It's like a whole new world when you're in good shape and VERY well dressed. Girls will be checking you out constantly, I mean, CONSTANTLY! You walk into a room, you'll notice the girls there look at you with the wide eyes, and for just a bit too long. Walking down hallways, you'll see the same thing, if not, quick glances(looking down when you turn to them). When it happens this much, you come to expect it all the time. It also helps if you've got an attractive face, but I think if you even had an average face you'd see pretty much the same results. Girls will be wide eyed and smiling at you when you decide to talk to them, without having even done anything. You'll notice some of the girls won't even look you in the eyes when you talk to them because they're so nervous in your presence(this is even moreso the case if you talk in a deep confident voice, which if you don't have already you'll aquire through this site).
To Windwork and anyone else serious about improving their image, good luck... It's not fair, but people judge you based on the way you look. If you do it right(buy the right kind of clothes), the change in the way people react to you(not only girls) and the way you feel about yourself will be your fuel that will motivate you to look the best you possibly can.
