10 Fresh (and Fun) Ways to Wear Dr. Martens in 2019

Trends cycle back every so often, and with that, certain pieces do as well. But if we had to pinpoint one fashion item that has been a consistent go-to staple throughout the years—regardless of time and trends—it's a pair of Dr. Martens. Since first being introduced in the '60s, the iconic work boots have always been worn, making them a true investment piece. And aside from being timeless (part of the reason it's been around for decades), the boots are extremely durable, meaning that if you buy a pair today, you can rock them for years to come. Which then leads us to our next topic—how to style the grungy footwear. Ahead we've rounded up an assortment of stylish outfits that have been grounded by the classic work boots. From teaming them with a playful midi dress to a little black skirt, here are 10 fresh (and fun) ways to wear your Dr. Martens this year.

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Christian Vierig/Getty Images

Style a patent leather overall dress with poppy white boots. The contrast makes for quite an eye-catching ensemble.

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Style du Monde

Team denim overalls with the classic black Dr. Martens for a cool but comfy outfit that you can wear all day long.

We love the idea of teaming a flirty dress with a pair of grungy work boots.

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Style du Monde

Pair the classic combat boots with an LBS—a little black skirt. Then add some texture to the otherwise clean pieces with fishnet stockings.

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Collage Vintage

Want something cool(ing) and practical? Then swap the little black skirt for a pair of cutoffs. And if it's too hot, trade in the oversize, off-the-shoulder sweater for a summery tank top.

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Collage Vintage

If you're feeling less experimental with your Dr. Martens, then go with a no-fail outfit pairing—skinny jeans, a cool trench, and, to ground the look, the classic black boots.

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Christian Vierig/Getty Images

Or try cropped flare jeans (and a cool crop top to go with it).

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Style du Monde

Play up the texture on top and then ground the look with platform Dr. Martens.

Or amp up the print. Pair a fun, flirty romper with your Dr. Martens.

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Christian Vierig/Getty Images

You can never go wrong when pairing a printed midi with classic boots.

Next up, see how model Kaia Gerber wears her Dr. Martens.