Look 1: A Cropped Sweater Vest Over an Oversized Button-Down Shirt Wear an oversized button-down shirt as a mini dress with a sweater vest on top, for a Gossip Girl -esque style.

Now, if you're questioning just what to wear with a sweater vest, we don't blame you. There are a few elements to consider, from what top to layer underneath (if any), to what bottoms you pair with it ...

Vest, $150, by Spiewak. Sport coat by Cool Hunting People. Shirt by Tommy Hilfiger. Tie by Neil Barrett. Jeans by A.P.C. Watch by Oris. Photo: Paola Kudacki 3/30 Buy a 3-in-1 Coat ...