I found in college, and still find, a backpack to be my most versitile form of luggage. I still use a backpack frequently for business travel, especially international. A good backpack is compact, comfortable, and easy to tote. Heavy loads or heavy traffic can make messenger bags a frustrating accessory. (Anyone who's been through the Southern China border probably knows what I mean). I bought a North Face backpack (not the cheapest, but also not $300), in a more subdued color for college (Ice), and still get good use out of it now. I can honestly say that IMHO backpacks, with previously addressed limitations, are extremely comfortable, functional and flexable. I prefer more outdoor or sport geared backpacks, as I personally feel they have an authentic (masculine) style all there own. Sierra Trading post or Campmor are good places to look for discounted ($50-100 bags). EMS sometimes has decent sales. Regarding building a collection: I, too, had a very similar body shape and size to you in college. I also wanted to start a better clothing collection, but was somewhat nervous of outgrowing items, or (due to price limitations) buying mid-grade items at a significant cost, but without the desired quality. I agree with the more moderate advice given by others. I also found that well-made ties were a great way to show your style, and can never be outgrown. And a classical tie can span generations. Although my first suit has long left my closet, some of my favorite (and most complimented) ties are from my pre-college and college days.