What to wear: Norse Projects bomber jacket, Buy It Now at Norse Store, $195; Cut and sew denim shirt, Buy It Now at ASOS, $54; Ruell & Ray canvas pants, Buy It Now at Art and Survival, $180; Converse sneakers, Buy It Now at Concepts, $90

If there's anyone who will plant a negative seed about you into your girlfriend's mind, it's her best friend. Meaning it's super important to get on her good side. You may think you're meeting her just to hang out, but she's judging you up and down. Simply put, you want to look like someone who has their shit together, but doesn't seem super square.

Try a simple piece of outerwear with an interesting shirt, a pair of canvas pants that wear well but look surprisingly dressed up, and a pair of next-level sneakers. It will be the perfect balance to win over her best friend's approval.