How To Wear Your Dr. Martens With Anything

Mini skirts? Menswear? It’s all fair game.

Love it or hate it, the 2014 Tumblr aesthetic is back. To quote The 1975’s front man, Matty Healy, while headlining the Reading Festival 2022 in the U.K.: “Wow, the ‘75 and Arctic Monkeys in the same weekend. Get your Dr. Martens and your fishnets and your vinyl and your Tumblr aesthetics — get ‘em all out!” With those two Tumblr-era bands releasing new music soon, along with Taylor Swift, Carly Rae Jepsen, and Sky Ferreira, we’re officially re-embracing Tumblrcore. And as much as Docs fit snugly into the 2014 soft grunge revival, the truth is that the iconic English footwear brand will never go out of style, which is why you should know how to wear Dr. Martens for every occasion.

Platform shoes and combat boots, in general, have had a big moment in the style zeitgeist in recent years. They can be found on red carpets, at fashion weeks (most recently the Vogue World Runway), in street style, and in many, many TikTok fit checks. “Who doesn't want a classic and timeless black boot to style their favorite fits with?” style content creator Marie Eriksson tells NYLON. “Especially nowadays, when people are becoming more aware of their shopping habits and would rather shop sustainably for timeless, quality fashion pieces that they are able to re-wear again and again.”

Part of the reason that Docs transcend trends is simply due to the fact that they are incredibly durable and last years, if not decades, given that they were originally designed as workwear boots. “I think that a lot of people are looking to simplify their wardrobe in a way that will last them years instead of a season or two — not just in terms of style, but also with quality and durability in mind,” fashion content creator Erika Dwyer tells NYLON. “For me, I purchased my first pair of Dr. Martens with this exact intention, to have a reliable boot that went with endless outfits in my wardrobe.”

Both Dwyer and Eriksson agree we’ll see even more pairs of Docs in the coming season due to the rise in grunge, punk, and goth style aesthetics. “They are especially trendy right now, due to the resurface of the ‘Tumblr grunge’ aesthetic,” Eriksson says. “‘Preppy grunge’ is another trend that's believed to be very popular this fall, an aesthetic where Dr. Martens would fit right in since they're perfect to dress both preppy and grunge! But to be fair, I think they fit pretty much all fashion styles.”

Everyone knows that Docs are the fall season shoe, but wearing them all year round is actually quite easy, given that the heavy-sole, yellow-thread shoes are arguably one of the most versatile out there. Here’s what the experts have to say about styling the timeless kicks no matter the season.

How To Style Dr. Martens For Cold Weather

Autumn and winter are “the best time to wear Dr. Martens, because you can finally wear the thick cozy socks that will prevent in those break-in blisters,” as Dwyer puts it. “An oversized sweater, black mini skirt, tights, thick socks, a trendy handbag, and my Docs is going to be my fall fit formula.”

If you’re sticking with skirts well into the winter, the cool “It Girl” vibe of the moment, Eriksson explains, is very centered around skirts and dresses with longer hems. “If you want to wear your Docs with skirts and dresses in cold weather, they also go really well with tights and a layered look,” she says.

However, Eriksson’s go-to staples with Dr. Martens in the fall and winter are trousers or jeans. “This fall I think we're going to see a lot of Dr. Martens paired with wide-leg trousers and jeans, and also baggy jeans, together with biker/leather jackets and trench coats,” says Eriksson. “The overall vibe will be somewhat casual with an edge.”

As a styling tip, Eriksson recommends making a conscious decision about whether you want your pants to go over your Dr. Martens or end right above them, especially if you have an ankle boot. “Wide-leg trousers is the most popular way to style them, and with good reason! I think that's a more subtle and elegant way of styling your Dr. Martens compared to the cropped or shorter-legged trousers,” Eriksson says. “Of course, they also look really cool with a cropped leg paired with some socks, but with the baggy jeans and maxi skirts in style, I really believe that the longer hemmed trousers [are] the ‘It’ style for 2022.”

How To Style Dr. Martens For Warm Weather

Because Dr. Martens are so versatile, you can pair them with just about any warm weather staple: skirts, dresses, shorts, and so on. “My favorite way to style my Dr. Martens is with a very feminine outfit,” Dwyer says. “I love the balance Docs create, especially the Jadon, with the weighty, elevated platform offsetting what might be lace and a soft color palette. I will also never get sick of seeing Dr. Martens styled in a moody, preppy style like dark academia.”

Eriksson shares a similar sentiment when it comes to wearing Docs with sunny day outfits, because one of the best things about styling combat boots is the ability to play with hard and soft aesthetics. “I absolutely adore the contrasting look with an edgier boot paired with a feminine summer dress,” she says. “Dr. Martens will definitely give you a whole other statement element [and] vibe to your look, which is something sneakers just never could. So dare to embrace it and just get creative with your summer styling.” For the spring and summer, she recommends everything from Dr. Martens with very feminine floral skirts and dresses to denim sets, blazer looks, and oversized graphic t-shirts.

Just note that wearing Docs under the sun will definitely turn up the heat a little. “Dr. Martens do a pretty good job at keeping your feet warm, so pairing it with an item that allows for airflow around the legs is key when wearing them in higher temps,” Dwyer adds.

How To Style Dr. Martens For Casual Outfits

When it come to Docs, casual outfits are the shoes’ forte. “Dr. Martens are perfect for a casual look, because they're already giving off that vibe,” Eriksson says. “It's kind of like wearing sneakers, really easy to dress down [and] casual, but harder to dress up, I would say.” She loves styling them with both jeans and trousers for an effortlessly chic and casual look.

“I think I love Docs with casual outfits the most because that is how I wear them 90% of the time,” Dwyer says. “It is hard to do any wrong when it comes to styling your Dr. Martens casually.”

Her easy go-to is a baby tee, jeans, and a vintage shoulder bag with Docs, but she’s partial to long white flowy skirts and plaid mini skirts as the ultimate way to go, as well as mini skirts over sheer black tights circa 2014 Tumblr grunge.

“What Converse were to dresses in the mid-2000s is what I feel Docs are to dresses now,” Dwyer says. “You can really wear them with any dress and it adds an edge — my advice would be to include other accessories to the look that match the vibe of the shoes.”

How To Style Dr. Martens For Going-Out Outfits

Given than Dr. Martens are almost the antithesis of formalwear, dressing them up for a going out look might require you to think a little harder about your outfit. “The easiest way to balance the casual vibe out is to add a clothing piece or accessory that we directly associate with ‘dressed up,’ which could be a matching set, an elegant dress, or something structured like a blazer,” Eriksson says. “You can also play with colors; a monochrome look (especially in neutrals) is usually more associated with ‘luxury’ and being ‘dressed up.’ Another trick could be to add some accessories, or add some matching elements to your outfit.”

Dwyer agrees, seconding the monochrome and menswear aesthetics as ways to make outfits with Dr. Martens look more refined and put together. “I like to go for an all-black moment when dressing up my Docs, as I feel like it looks a little more polished,” says Dwyer. “I also like to feature more luxe textures like silk or leather when trying to elevate the look. The oversized suit and Docs look is a great option to dress up Dr. Martens if you aren’t wanting to opt for a dress — I think the tailored look with the grungy feel of Docs is a great pair.”

The thing about styling Dr. Martens is that you really can’t go wrong. Sure, they’re uber-trendy right now, but they’ll also be just as cool in a few years — and not to mention still intact, which is more than lots of other trendy footwear can say. “Since they are so versatile, my advice would be to just stay true to your authentic personal style and dare to experiment,” Eriksson says. “I promise you, Dr. Martens will fit any aesthetic or fashion look you want to go for.”

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