Thursday's Wingtip boots are available now in black and brown, and on October 20, they'll be dropping a cognac suede pair. Same deal—hard to mess up, wear 'em with everything, but with that 1UP ...

Among them are a classic white button-down shirt, a pair of white sneakers, a pair of Chelsea boots ... size 16, the best-selling Rothy's Driving Loafer and the Cole Haan Men's 4.ZERØGRAND ...