17 Dr. Martens Outfit Ideas to Try This Fall
Forever a fall staple.
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I’d bet a fair amount that everyone I know owns at least one pair of Dr. Martens boots. I remember buying my first pair ahead of Coachella: They were the all-white 1460 Boot that I’d definitely seen on Tumblr. Then came my more practical black chunky Jadons. Both still live in my closet today, and come in handy for rainy days, festivals, or when I’m feeling a little edgy. That’s the beauty of the Dr. Martens boots! They’re durable, go with virtually any aesthetic, and will never go out of style. Fall marks the season of Docs, and to celebrate, we’ve rounded up 17 outfit combinations—spanning wardrobe staples and trendy silhouettes—to wear with Dr. Martens.
Skirt and Jacket
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Play with aesthetics and pair a cute mini-skirt with edgy black Dr. Martens. The two create a fun balance that feels modern and fun. On chillier days, style the look with a blazer or jacket.
Model Off-Duty Formula
Put a twist on the classic model-off-duty formula and swap the sneakers and flats with a pair of Dr. Martens. This outfit features items you probably already own, like a blazer and medium-wash jeans, that can be mixed and matched with similar classic silhouettes.
Dark Wash Denim
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Denim jumpsuits and dresses feel equal parts polished and fun, and the addition of a black chunky boot adds a casual, on-the-go energy. This short jumpsuit, black bag, and boots combo are perfect for festivals or casual outings.
Fall Staples
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Dr. Martens belong in any go-to fall outfit formula, but look especially fitting when paired with a trench coat and jeans. The neutral pairing acts as a great canvas for adding personal flair with layers and fun accessories or colorful eyeshadow.
Cozy Sweater and Sweats
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Dr. Martens may feel like a statement piece, but they’re a perfectly practical option when the weather is dreary and you need a protective boot. On cozy days step out in a comfy sweater, sweats, and boots.
Jorts and a T-shirt
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Have you tried the “Adam Sandler” outfit yet? It consists of baggy shorts (a transitional fall staple) and whatever top your heart desires. The easy outfit formula just makes sense with black Dr. Martens.
Plaid Set
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Dr. Martens and plaid go together like peanut better and jelly. Lean into the ’90s of it all with a plaid set and edgy fishnets.
Blazer and a Dress
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You can still wear dresses come fall, and this outfit is proof. Dr. Martens and a jacket layer like a blazer helps keep you warm, and a silky dress adds a fun texture that can be shown off once it’s sunnier in the afternoon.
Crop Top and Maxi Skirt
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The perfect counterpart to long, sweeping maxi skirts? A pair of platform boots. In the in-between period of summer to fall, opt for a similar outfit formula of a tank top, maxi skirt, and Dr. Martens.
Turtleneck and Wool Coat
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Contrary to popular belief, Dr. Martens can look luxurious. Although the shoe is often associated with its edgy ’90s roots, Dr. Martens look like their more expensive counterparts when worn with a plush turtleneck and wool coat.
Breezy Dress and Sunnies
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Think of the “wrong shoe theory” here. Although you’d think to pair a dress with flats or heels, the chunky boots add an unexpected feel that makes for a thoughtful outfit combination.
Classic Barn Jacket
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ICYMI: Barn jackets are having a moment. Take Bella Hadid’s New York street style fit as inspiration and style the country-core piece with boots, flared jeans, a vintage shirt, and eclectic accessories.
Activewear and a Blazer
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For when you have pilates at 6 PM but drinks at 7, throw on a pair of Dr. Martens and a blazer over biker shorts and a top for a sporty-chic look that gets the job done.
Bold Dress and Sandals
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Dr. Martens has way more to offer than its classic lace-up boots. The brand’s chunky sandals are the perfect way to add some edge to a printed maxi dress, even in the late summer heat.
Plaid Skirt and Baby Tee
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Olivia Rodrigo might have singlehandedly revived our love for Dr. Martens during her grungy, goth-rocker phase. In this look she’s wearing the boots with a ’90s-esque tartan skirt and a baby tee.
Matching Set
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The easiest outfit combination of all time has to be a matching set—it’s done the styling for you. Here, the styling prowess of Dr. Martens is on full display, and the cute ribbon laces compliment the feminine tweed set.
Oversized Sweater and Leggings
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Throw it back to the Tumblr days with an oversized sweater, leggings, and Dr. Martens. Perfect for lazy days mid-fall when it’s too cold to wear open-toed shoes or sneakers, a statement sweater like this one adds a pop of color to the monochrome look.
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