Rihanna
While we wouldn't recommend whipping out your old, college sweats, there's no reason you still can't be comfy in sweat-like material. Try a loose-fitting, easy jumpsuit like Rihanna 's DKNY number. She dressed it up with a pair of on-trend, mesh heels, but we think a pair of wedge sneakers would be just as sporty-chic.
[Photo: Rihanna via]