New Year's Eve
What to wear: Tuxedo jacket, Buy It Now at J.Crew, $525; Tuxedo pants, Buy It Now at J.Crew, $265; Alden shoes, Buy It Now at Shoemart, $418
If you're single, you can chug Natty Ice with your boys on New Year's Eve until you pass out at 11:30 p.m. If you're in a relationship, things are going to be different. You might not own a tuxedo, but this a rare opportunity to wear one. Your girl is going to expect some really special shit, so pretend like you're in the Jay Z "Roc Boys" video and get dapper for this annual event.
You're going to live like it's The Great Gatsby for one night; Make sure you dress the part. She's going to be wearing one of her fanciest dresses, so don't make her ashamed to be giving a midnight smooch to a dude in a graphic T-shirt and baggy pants.