First introduced in the '70s, Dr Martens' Chelsea boots are a rugged rework of a classic silhouette. The smooth leather is famously tough at first before softening over time. The elasticated panels will afford you a bit more room during the first few wears. They're set on tough air-cushioned soles, and reinforced with yellow welt stitching. Wear yours with jeans or wool trousers for a smarter look.