The Street Tray sneaker from ECCO is an updated classic. Featuring gum rubber outsoles for style and grip, and absolutely awesome two-tone leather uppers, these will be able to dress up with a sport coat, dress shirt, and nice jeans, or dress down with shorts and a t-shirt. A leather and textile lining provides a soft and breathable feel around the foot. Six eyelets (plus an extra towards the ankle) also means you get a nice, custom fit.

Available at Glebe Trotters.