Matt Halfhill knows sneakers. Being a guy who dresses from the shoes up, it’s important that his cuffs both compliment and protect his kicks. "You know, it's all about the shoes," Matt says. "My favorite types of jeans are the ones that work best with whatever sneakers I'm wearing,"

After choosing his favorite style 501®s, Matt had the Levi’s® tailors chain-stitch a red customized cuff for his classic New Balance kicks.

Want to win your own custom-cuffed 501®s? Simply post a pic of your favorite 501®s-and-kicks combo to Instagram using #501 and #cuffsandkicks, and Matt just might select you as the lucky winner of a trip for 2 to the Levi's® Tailor Shop in San Francisco. For more info on how to enter to win, be sure to check out complex.com/levis501.