What to wear: Crewneck sweatshirt, Buy It Now at Supreme, $136; T by Alexander Wang sweats, Buy It Now at Forward, $225; New Balance sneakers, Buy It Now at Bodega, $160; RAW 5-panel hat, Buy It Now at Brick Harbor, $36

Before you tell someone you love them, you're probably going to be super nervous. Sure, it should come naturally, but this is the make-or-break moment for your relationship. Don't be corny and have it all planned out, just go with the flow. Say it when you mean it. For the ocassion, you just want to be you, so wear an outfit that's a typical representation of your individual style.