This is a subject I feel well qualified to comment on. Seeing as I've spent the last 6 years of my life in college, 4 in a mid-sized public school in the midwest and 2 at a large public school in the south. Over that time I've gone from on of the worst dressed people to one of the best dressed. Now there were some mistakes along the way, I regret to say #2 (or something near it) was one of them. The hardest thing to learn was now to be well dressed without being "dressed-up". That said, being well dressed has opened up many opportunities, if nothing else because if gives women something to compliment you on. For me, I find that slim cashmere sweaters work great (I like j-crew's v-neck. if you wait for a sale, you can get them pretty cheap), with a nice dark pair of slim jeans (Gap seems to do this pretty well for a reasonable price) and good shoes are a must (I have a pair of black RL Rivington's and chili AE McClain's that I switch between. These almost always illicit compliments. If you're feeling more casual, I recommend a nice clean white tennis shoe, I wear Converse Jack Purcel). Tie's are optional, depending on mood. If you wear a tie, keep it skinny. Most of mine are between 2-3". This general framework has worked for me. I've actually had women stop me in the halls to say "Whoa, you should totally thank whoever taught you how to dress, because they did a great job" or at the bars say "I've seen you around. You're always really well dress. Are you single..." I'm a fairly good looking guy, not a stud, but I can hold my own. I whole heartedly believe that the way I dress was open doors for me with women that would otherwise be out of my league. Of course, be aware that some women prefer someone more casual. I has an ex girlfriend who hated the way I dressed (but she dated me anyway, so wtf?) I should also note that this seems to work for a wide range of ages, from 18-19 to women in their late 20's early 30's. FWIW I'm 23.