Need to raise up your look, but still want to keep one foot firmly planted in your sneaker world? Introducing Mr. Sneaker Chukka. While it won't pair with your interview suit, this boat shoe-vs.-sneaker-vs.-sand boot mash up will sharpen any casual set. Perfect for that third date or the Saturday night prowl. Vans (above), Nike, Adidas, Chrome and upscale brands like Lanvin, Alife are all pumping them out. Only rule: Keep 'em fresh and clean, son. Just like dirty sneaks, skuzzy chukks suck. Vans Suede Chukka, $60, shop.vans.com.