25. Drake

L.L. Bean Cable Knit Sweater, $159
Ray Ban Original Wayfarer, $150
Gold Chain, $5
Pinky Ring, $150
Rosé, $15

Heartbreak Drake's been dropping panties since Jimmy played basketball in a wheelchair. From a female's point of view, this guy can do no wrong. Want to get laid after the Halloween party? Just rap his lyrics from the lovey dovey "Best I Ever Had" to the somewhat disrespectful "She Will" and even "Every Girl" and you'll have all the chicks calling you the man of their dreams. Just go easy on the cups of the rosé.