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Also known as Chelsea boots or jodhpur boots, ankle-high dealer boots feature rounded toes, low heels, and two strips of elastic up the sides for flexibility and comfort. Designers created them as walking shoes and they quickly became popular with artists and fashion icons during the 1950s.

The Beatles and Rolling Stones wore dealer boots, increasing their popularity during the '60s and making them a future staple of men's footwear. For a classic, simple look that goes with nearly any outfit, choose dealer boots.