Whether you're taking your favorite girl to her favorite spot or checking out the latest bar with your closest friends, you can't go wrong with this classic and cool outfit.

Buck Mason Natural Lightweight Army Shirt, $145

Tanner Goods Leather Dress Belt, $149

Farer Carter GMT Watch, $525

Billykirk Leather Card Case with Flap, $39

Buck Mason Black Slim Jean, $175

Greats The Rosen Sneakers, $59