Work boots get the comfort of all-day hikers with the Timberland Pro Endurance Boots ($130). Featuring anti-fatigue technology and the PowerFit system, these boots feature an impressive 5-layer footbed, polycarbonate hardware, climate control (to regulate temperature and control moisture buildup), a dual-density oil-resistant outsole, a rubber-coated steel toe, and a flexible Steel-Flex puncture resistant plate.
Kick it old school with the Diadora Heritage Collection (£95, ~$170). These retro-styled Equipe sneakers feature suede, leather, and canvas details in contrasting colors, with washed out uppers that make them look like they've been with you for years. You know, sorta like how your psycho ex-girlfriend described your relationship — "It feels like we've been together for years!" — but without the ugly restraining order.