We've seen some high tops in our day, but this is ridiculous. Under Armour Charge Basketball Shoes ($130) feature a two piece upper that's designed to articulate around your ankle, locking down the fit — it essentially acts as an ankle brace — while enabling greater flexibility. Other features include breathable HeatGear materials that wick away sweat, Micro G cushioning for comfort, and an integrated sockliner. Available in blue/silver, black/blue, grey/yellow, and red.
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.