Thom Browne has cultivated an aesthetic that's at once preppy and subversive. These well-made nubuck chukka boots are detailed with broguing and wingtip toes for extra rakish appeal. The exaggerated welts and chunky crepe soles add even more off-kilter edge, along with a good dose of impact-absorption. Try yours with cuffed denim in a deep blue or black wash. Shown here with a Thom Browne shirt, coat, trousers and scarf.

• Black nubuck chukka boots
• 2-eye construction with silver eyelets, signature striped pull tab, brogue and wingtip detailing, rubber crepe soles, leather linings and lightly cushioned footbeds
• Lace-up