Nothing can transform your look like a pair of slim-fitting khakis rolled up at or just above the ankles and paired with some canvas sneakers. But even better, the look of rolled up chinos allows for you to use any shoe you want with any pants you want because you don’t have to worry about your pant-cuffs dwarfing your topsiders or looking awkward with your brogues. Street-friendly, this look is part of the repertoire of the Ivy League Look of the 60s. Sport some Weejuns with socks, or some Sperry’s without. Rolled up chinos also aid in dressing down a jacket that you’re eager to wear around campus without looking too fancy. (Photo credit to the Sartorialist).