Walking in the city can be rough — so outfit yourself properly with these Cole Haan Waterproof & Reflective Wingtips ($280-$330). Available in Cooper Square and LunarGrand styles, the waterproof versions are seam sealed to keep water out, while the reflective versions feature panels of light-refracting material in between smooth leather. No matter which you choose, you can count on a subtle grey colorway accented with striking splashes of pink.
This year saw LeBron win his first NBA championship, so it only makes sense that his followup sneaker boasts a number of firsts as well. The Nike Lebron X ($270) is the company's first signature shoe to offer Nike+ Basketball support, which lets you track in-game activity via your iPhone, and is the first Nike shoe ever with a full-length visible Nike Zoom unit. Modeled after a diamond, the shoe also offers Hyperfuse construction for a one-piece upper, Flywire technology for a secure fit, and a lightweight feel. Available in three colorways.
Like it or not, winter is coming, and in many places that means cold days, bad weather, and heavy coats. It also means it's time to don some appropriate footwear, like The North Face Back-To-Berkeley Boot ($100-$110). A mix of classic styling and new-age materials, the Back-To-Berkeley features a ballistic mesh upper, a waterproof suede mudguard PrimaLoft Eco insulation, HydroSeal waterproofing, and a TNF Winter Grip outsole for excellent traction no matter what's covering the ground.