25 Ways To Wear Classic Doc Martens No Matter Your Personal Style

There's a lot to love about Doc Martens: They're timeless, durable, and go with pretty much anything. And there's no better time to take out your classic Docs than right now. With soft grunge looks taking center stage and the Tumblr girl aesthetic being revived in the form of indie sleaze, classic Doc Martens are the versatile shoe to give your closet that punk-inspired edge.

Originally a working shoe, Doc Martens built up its big reputation over decades. Though the brand traces its history back to 1901, it's really the 1960s that changed how we view Docs with the invention of the 1460 Dr. Martens (which is still a popular silhouette today). From the '60s onwards, through decades of social change and upheavals, Dr. Martens were picked up by fringe groups around the world. From anti-government groups in Britain to grunge and emo subculture in the United States, Doc Martens became a symbol of anti-establishment and self-expression. As they grew and grew in popularity, that sentiment was never entirely lost.

Doc Martens are now pretty solid in mainstream fashion today, but they still capture that original rebellious spirit, giving a bit of edginess to any outfit you pair them with. Classic Docs can truly go with anything, and we'll prove it: Here's how to wear Doc Martens, regardless of your style.

Baggy jeans

Oversized is in right now, and there's no place where the trend is more obvious than in current jean styles. Baggy jeans are casual, cool, and, best of all, comfortable. To complete that "cool girl" look, pair them with classic Doc Martens. The slouchy look brings us back to skater-inspired street style. Plus, the height on Doc Martens (especially if you have a platform style) can give you a bit of a boost if you find many baggy jeans too long, making Docs one of the best types of shoes to pair with your baggy denim

A cute mini skirt

It's pretty much impossible not to look chic when pairing Doc Martens boots and a mini skirt. Combining the two strikes the perfect balance between feminine and grungy. The chunky boots offset the look of a sleek skirt silhouette and gives some contrast to your look. Best of all, Doc Martens pair well with any style of short skirt, including schoolgirl, plaid, classic black mini, or a girly floral or frilly style — there are so many ways to rock this look.

Denim shorts

Doc Martens boots aren't just a cold-weather shoe; you can rock them in the spring and summer too. When paired with some cut-off denim shorts, they give the outfit a bit more edge than your typical sneakers or sandals. They'll keep your feet more protected, too, for when you're out and about. If your Docs are nicely broken in, this is a comfortable outfit for a day walking around the city. This punk-inspired look looks great with both black and blue denim shorts.

Midi-length skirt or dress

Another look perfect for summer, Doc Martens also pair well with an edgy midi skirt. It's another dichotomous coupling, combining a flowy and feminine midi silhouette with a chunky and more masculine boot. Depending on the skirt and how you layer the look, this pairing can also work as a fall or winter outfit.

Bike shorts

There's something about the bike shorts and Doc Martens pairing that screams model-off-duty. The bike shorts say you're on the go, while the boots show that you want to look just a bit cool and put-together. It's a little edgier than your typical athleisure combo of shorts and sneakers. Plus, it's hard to fault how comfortable this outfit is.

Long and flowy skirt

Looking for more leg coverage? Turns out Doc Martens look just as fabulous with a maxi skirt as other skirt lengths. Opt for one that stops around the top of the boot to keep the Docs on full display, like in this outfit. Get the most out of your maxi skirt and go for a longer style to cover the boot and offer a peekaboo effect. Another thing we love about this outfit? The band tee — it goes perfectly with a pair of Doc Martens for that rocker chick look.

Comfy sweatpants

Sweatpants and sneakers are a classic combination, but if that's feeling a little too basic for your day, pair your sweatsuit with Doc Martens instead. This outfit has all the comfort of a sweatsuit outfit, but with a bit of edge. It's the less obvious choice of footwear, and that's exactly what makes it more fashion-forward. And you'll look cool and be comfortable.

Little black dress

A little black dress is a closet must-have, no matter your style. If you've pulled out your LBD for a night out but aren't in the mood for wearing heels, Doc Martens can give your outfit that put-together look, but in a much more comfortable way. While they won't replace heels in all situations, they can offer a more formal look than sneakers, as long as they're paired with the right dress. Since the boots have a bit of height, they can make you look a little taller as well.

Skinny jeans

Sure, we've talked about why you might want to ditch your skinny jeans, but let's be real — they're a mainstay in many closets, and some variation of them is sure to come back in style in the future. If you want to update a skinny jean look, pair it with a trendier shoe like Doc Martens. There really is something timeless about a skintight pair of jeans and combat boots. It gives an outfit a nostalgic 2000s emo-punk look that we can't help but appreciate.

Sheer tights

A classic combination, Doc Martens and sheer tights are a go-to look for coming across as put-together with just a touch of sultriness. Grab a pair of new tights (ones without accidental holes in them) for a more preppy look, or go for a pair of ripped tights instead to create a look that aligns with the rebellious spirit of Docs. Sheer tights can add to a range of Doc Martens outfit ideas: Wear them under a mini, midi, or maxi shirt or even under shorts to add an edge and keep warm. They also look fabulous with a pair of leg warmers over top.

Classic trousers

Take your Doc Martens back to their work boot roots. The Doc Martens and trouser coupling is one way to use Docs to create a daytime-to-nighttime look. These classic boots are appropriate for casual offices but also cool enough to wear out for an evening on the town. They bring a bit of edge to clean-cut trouser outfits, making the fit feel less formal and changing the vibe entirely from "clean girl" to "cool girl."

Cozy leg warmers

The balletcore fashion aesthetic has leg warmers popping up all over our feed — and we must say, we love the comfy and cozy look of it all. Today's trending leg warmers are not the bright leg warmers of the 80s but come in more subtle, neutral tones. We love how they soften the look of Doc Martens. Plus, since they cover the top of the boot, it gives the illusion that you could be wearing a whole new shoe, like a Docs loafer. Adding leg warmers is a good way to switch up your look, and it doesn't hurt that they add a bit of warmth to your outfit as well.

Fishnet stockings

Fishnet stockings are another Tumblr-era trend making its way back into our closets. It can be hard to style fishnets, but one way to do so is with Dr. Martens boots. Paired with a chunky boot, you can really lean into the grunge look. Make it more fun with different variations of fishnets, such as bedazzled or multi-colored styles. And just like with tights, a few holes in your stockings don't matter — it actually just amps up the indie sleaze style to this look.

Plaid pants

Plaid is a mainstay pattern in soft grunge looks. Pair plaid pants with your Doc Martens to easily achieve this aesthetic. This look is another one that brings us back to our Tumblr days when plaid dominated our feeds. We love how this outfit incorporates this preppy element into an otherwise rebellious look to serve us "good girl gone bad."

With a classy blazer

Style your chic blazer outfit with a pair of Doc Martens. Blazers are oh-so-cool, but for some of us, they can feel a bit too stuffy and formal. Doc Martens boots take this look from an office-chic look to an edgier city-girl vibe. The bright blue color makes it stand out even more as a stylish pick.

Denim skirt

Denim and Docs just work, and one way to pair the two is with a denim skirt instead of jeans. Long denim skirts are making a comeback against all odds, and we especially appreciate how this pairing works year-round. You can opt for a short denim mini skirt and a crop top in the spring and summer. Or, for fall and winter, dress along the lines of this outfit with a midi or long denim skirt and a sweater to keep warm.

Oversized jacket

Square shoulders and oversized silhouettes recall a popular 90s look that still looks modern today. There's something that looks just right about Doc Martens and an oversized coat. Together, they make the perfect combination that's cozy and looks totally effortless (even if you actually put a lot of thought into it).

Straight-leg jeans

Straight-leg jeans flatter every body shape. Plus, they go with absolutely every shoe out there, including a pair of Doc Martens boots. This jean length shows just enough of the boot for it to be recognizable, but not the whole shoe. It makes the outfit flow seamlessly together.

Wide-leg jeans

Cover a little more of your boots with a wide-leg jean, which changes the look to make it a bit more trendy rather than punk-inspired. The boots above elevate these classic medium-wash blue jeans. There are a lot of jeans looks on this list, which we hope goes to prove that Doc Martens work with all denim styles.

Leather pants

Leather pants have an air of rebelliousness and defiance, making them the ideal partner for Doc Martens. If you really want to channel Doc's anti-establishment sentiment, do so with black leather pants. They really just complement Doc Martens boots beautifully. Or, to add a twist to this look, colorful leather pants (like a bold red or maroon) give the same vibe with more originality.

Patterned pants

When you're in the mood for a bold outfit, pair a set of loud, patterned pants with your Doc Martens. These pink leopard plants look more elevated with a pair of Docs than they would with sneakers! While Doc Martens are distinctive, it's nice that they're on the plain side since you can wear them with patterned clothes. Especially if you have a black or white pair, they won't clash with the pants pattern, but they'll just add a carefree edge to your outfit instead.

Knee-high socks

Knee-high socks are a staple you'll want to integrate into your closet. Add a skirt, and it gives an ultra-preppy uniform vibe. However, the entire ensemble is elevated when paired with platform Doc Martens. Doc boots give this outfit an edgier feel than loafers or Mary Janes would while still maintaining its cutesy appeal.

Flared leggings

With a recent trend towards wider leg silhouettes, it's no surprise that flared leggings are making a comeback, taking over the skinny leggings of previous years. You may think leggings pair best with sneakers, but you may change your mind after seeing this outfit. It's equal parts cozy and fashionable, so it's a good choice for when you want to look like you made an effort in your outfit while also prioritizing comfort, like running errands or going to appointments.

Tucked in

If you want to make your Doc Martens the star of your outfit, tuck your pants into them. Whether you opt for slim-fit jeans or baggy track pants, tucking them in really showcases the boot. Even though the clothing is bright and bold, your eyes are automatically drawn to the boots in this outfit.

Ribbon laces

With their utilitarian style, Doc Martens are pretty gender-neutral, if not leaning towards masculine. If you want to add a feminine touch to the Docs themselves, string through some ribbon laces. Black laces stick to the more edgy look of the boot, but you can also opt for different colors to show off your personal taste.