9. The Boat Shoe — While not for everyone, once the temps start climbing up, we can't resist slipping into something a bit nautical (we can almost pretend we own a yacht.) And, while you might not be facing any Perfect Storm-type scenarios, they're definitely equipped to handle some heavy puddle hopping. Plus, they're just so easy and comfortable — you can always throw 'em on sans socks. Ahoy!

GBX Fidlar, $65, available at GBX; Thom Browne Leather Brogue Boat Shoes, $520, available at Mr Porter.