My tip: If you wear thick socks and keep a few blister bandages handy, you'll be fine. That said, here are my five favorite pairs of Dr. Martens boots and sandals that I would buy again.

You can even bag a pair of Double Doc Organic Cotton Blend Socks, £12, specifically designed to be teamed with the brand’s boots and shoes. Dr. Martens also recommends massaging the leather on ...