Timberland boots are well known by working men and rappers alike largely for the same reasons. Their beefy looks, comfort, and durability are simply hard to match, especially for around $100. Feeding off that heritage, Stussy and Timberland have collaborated to create the Stussy x Timberland XXXth Anniversary Desert Boot ($195) which mix elements of the classic work boot with the style of more casual chukkas for a final product that’s a nice change from the mass of more “metro” offerings currently flooding the market. Constructed from premium suede and a Vibram sole, they have all the details you’d expect from a pair of $200 boots. They also ship with a sets of bright orange and “natural” waxed top laces so you can mix things up. A version in black suede with a set of blue laces is available as well should you prefer something darker.

Buy Now: $195