Oh man, these take us back. Nike's old-school sneakers are potentially the most versatile ones on the market. We wouldn't judge you for wearing them every day this summer—with a suit, jeans, shorts, chinos, a bathing suit, or whatever else you've got. They're perfect when clean, but even better with a little scuff and grit on them. Maybe you'll even play tennis in them. $125, available at TresBienShop.com