Wow, We might be separated twins. Mid 20's, 5'6 as well, we dress about the same, and I to want to transition from college/frat look to good looking young professional. I got a good head of hair though. To get the confidence part, thats something that you can't buy, you just have to have it. Think well of your self, you sound like your doing good. You sound like you might be in a better place then me, Im single and 1/2 way to a college degree (my first), and have worked at various jobs I hated, and my current living situation is almost insane. I feel you on the mid 20's , how do I dress problem. You feel like you want to dress like how you always have but at the same time, you don't want to look like a kid, as you feel your getting a little to old for that. Take a look at the non-street wear forum on here, these guys are good, and their stylish. But if your just starting out (with suits and good clothes) start out with something conservative, as it will last longer then something thats the current trend. Conservative suits almost always look good, if you get them done right. I'll also say, I bought a suit and nice clothes, but I haven't had a reason to wear them unfortunately. I worked a blue collar labor job for a while, and wearing a suit wasn't an option, hell wearing anything fancier than cheapo blue jeans was looked down upon. And after work, I'd have no reason to wear a suit or some of the nicer way's people dress on here. Although I wish I could. Nice shoes, nice suits, nice watches, wish I had a reason to buy and wear them but I currently don't. As for dressing better than the average frat guy, im clueless, but this form helps me little by little not dress as bad. The best thing you can do for you self is get in good shape and eat well and treat your self well. If I were to dress more then blue jeans when I go out, i'd look very out of place in this city, it's mostly blue collar and the only one's who dress up when they go out are the Mormons. And no im not in Utah. Good luck.