What to wear: Casual blazer, Buy It Now at Club Monaco, $250; Chinos, Buy It Now at Uniqlo, $40; Our Legacy oxford shirt, Buy It Now at Cali Roots, $150, Cap-toe shoes, Buy It Now at L.L. Bean Signature, $179
Valentine's Day is corny, but it might still mean a lot to her. Like your V-day plans, your outfit should be respectful, in good taste, and representative of where you're taking her that evening (besides Pound Town). Try to class it up a bit but without putting on costume-like formalwear. Break out a blazer and dressy chambray shirt, a pair of chinos or dark denim, and give your sneakers a break and roll with a pair of cap-toe shoes.