For some advice on how to dress for your body type I suggest reading this link, The Style Blogger knows what he's talking about: http://www.thestyleblogger.com/3035...tips-for-shorter-guys-featuring-adam-lampell/ I'm also 19 and on a college student budget except I'm a little taller then you, I'm 6' and 125-130lbs. I to started with Express shirts but learned quickly. I'd suggest you looking into buying some Rugby by Ralph Lauren oxford button down shirts. They are very versatile and go with almost everything. A size small on you would be perfect. A great thing about Rugby is that if you are a student and show a student I.D. they will give you 15% off anything you buy. http://www.rugby.com/shop/item.aspx?productId=11884483&categoryId=3372180&cp=3138868 As for the jeans, I personally do not like Levi's that much because I can never find a correct fit because I'm tall and skinny, but that might not be the case for you. If you did want to invest in some better jeans I'd suggest getting a pair of APC New Standards, which are about $175. That probably seems very expensive but the reality of it is, you can (and should) wear these same jeans everyday for a year+. http://www.contextclothing.com/item.php?id=6 For the shoes, I'd suggest buying two pairs of shoes, each relatively inexpensive. First, a pair of Sperry Topsider Authentic Original boat shoes. About $75, and they go with just about everything. They can be worn in the dry warm weather, they can be worn in the rain, and even in the snow (I live in D.C. and walked through several snow storms with these last year). The second pair of shoes you should buy are a pair of beeswax Clarks Desert Boots. These are also very versatile shoes. The can be worn with shorts, jeans, or even dressier pants. They are good in cold and warm weather and if you apply some waterproofing oil to them, they can even be worn in the rain. http://www.sperrytopsider.com/store...60&stockNumber=0195412&showDefaultOption=true http://shop.nordstrom.com/s/clarks-originals-desert-boot/3171407?origin=category&resultback=847 Good luck finding whats right for you! And I hope this helped.