Buy It Now at 3sixteen, $220

Jeans are probably the most versatile item in the modern guy's wardrobe today. That said, you should make sure your go-to pair are the most dope ones in your closet. 3sixteen's denim is made of quality Japanese fabric, with a fit that isn't too tight or too baggy, resulting in an overall clean silhouette you can rock with anything—sneakers, sportcoats, you name it.