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There’s a reason Dr. Martens is such a well-known brand that has remained at the forefront of all the latest trends in footwear. Throughout the years, the English company, which was established in 1947, has pulled off successful collaborations with Marc Jacobs, Keith Haring, Lazy Oaf, and Jean-Michel Basquiat, just to name a few. Doc Martens are more relevant than ever, with models, editors, and creatives making the brand’s combat boots and lug-sole loafers seasonless wardrobe essentials that help achieve a quintessential ’90s and 2000s vibe. Doc Martens complete a variety of looks, from a breezy dress to jeans and a T-shirt to oversize suiting. Their versatility is what makes them a transitional shoe option that’s worth the investment.

While Dr. Martens has stayed pretty committed to the classic combat boot – continuously reinventing the wheelhouse when it comes to churning out slight variations on the silhouette – other footwear labels have taken note and adapted the look. Prada’s chunky loafer with the metal logo on the upper, for example, takes inspiration from the same decade, while Ganni developed quirky details for the beloved shoe, like buckle closures rather than laces and a creeper-style rubber sole.

Whether you’re looking to build outfits around your Doc Martens specifically or you’re into the appeal of the aesthetic and open to trying any number of similar lug-sole loafers and boots, you’ll appreciate the 35 creative ways to build an outfit around these stylish and comfortable walking shoes. Keep reading for foolproof Doc Martens outfits appropriate for all seasons of the year.