Andy Samberg is one lucky guy. Not only does he have a great job (who wouldn't love getting paid to sing fake love songs to Mahmoud Ahmadinejad?), but he also dated Natalie Portman. Fortunate bastard.

Andrew Whanson Chicken Man T-shirt: ($28 from Yellow Rat Bastard)

American Apparel Salt and Pepper Zip Hoodie: The gray hoodie sweatshirt: where middle school gym teachers and indie kids see eye to eye. ($40 from American Apparel)

Union Straight Legged Jeans by Big Star: Samberg doesn't seem like the kind of guy who'd spend $300 for a pair of jeans. ($78 from The Denim Shop)

DKNY DY 4506 Eyeglasses: Break the homogeneity. Not everyone needs to wear black, rectangular plastic frames. ($108 from Framesdirect.com)