How to Style Dr. Martens Boots (and Not Look Like a 1994 Mall Rat)

Give your casual lace-ups a style boost by replacing your go-to jeans with an equally versatile—and surprisingly warm—faux-leather pant. Opt for a classic straight-leg cut in black leather to really maximize the number of outfits in which you can make this swap.

Shop similar styles: Chico’s Elongated Faux-Leather Shacket ($169; $80); Club Monaco Turtleneck Sweater ($190); Abercrombie & Fitch ’90s Straight Pants ($110); Dr. Martens 1460 Boots ($170)

Docs and miniskirts are a very cute combo, but if you want to avoid looking too much like a ‘90s high schooler you can add a tailored jacket into the mix. A blazer is perfect, but just about any polished topper will help make your outfit look overall more grown-up.

Shop similar styles: Everlane Oversized Blazer ($228; $171); Madewell Oversize Button-Up Shirt ($85); LOFT Button Miniskirt ($70; $50); Swedish Stockings Svea Tights ($35); Dr. Martens Tarik Boots ($140; $110)

Going for all black on bottom can potentially elongate your stems, but if you’re also rocking a cropped jacket suddenly your proportions can feel totally out of whack. Instead, opt for a lighter color boot, like these bright white platforms to help shake things up and keep your figure looking fabulous.

Shop similar styles: Sanctuary The Shacket ($129; $78); Topshop Turtleneck Sweater ($68); AE Ne(x)t Level Jeggings ($40); Dr. Martens Jadon Boots ($200; $156)

The perfect spot for cropped pants to end is either right at the top of your Dr. Marten boots or just below, so there is maybe a half-inch to an inch of overlap. This ensures your legs won’t look oddly cut off mid-shin, nor will your pants start pooling around your ankles.

Shop similar styles: Tory Burch Collared Sweater ($548; $409); Faherty Strecth Surplus Pants ($168); Dr. Martens Jadon Pisa Boots ($200)

Chunky, black Dr. Martens may not feel like an obvious choice for spring, but we love this look pairing them with a dark floral maxi. If you want to add a jacket, pick something that hits right at your natural waist rather than a longer style to help emphasize your waist. Bonus: Leather Docs will keep your feet cozy and warm in an unexpected spring rain showers.

Shop similar styles: Tanya Taylor Bria Dress ($575; $288); Aldo Rotorua Bag ($60; $50); Dr. Martens Audrick Boots ($200)

One of the best styling tricks we ever learned was the Sandwich Dressing Rule. Basically the rule says you should balance one piece on your bottom half with another on your top half, and include something contrary in the middle. In this case, the white boots are balanced by a white tee up top, with khaki green trousers in between, to ensure neither piece feels too out of place.

Shop similar styles: GAP Faux-Leather Blazer ($128); Madewell Whisper Cotton T-Shirt ($20); By Anthropologie Bungee Parachute Pants ($128); Dr. Martens 1460 8-Eye Boots ($150)

If you have a pair of colorful Dr. Martens, try putting together an outfit with pieces that all fall within the same color family. For instance, if your boots are burgundy, a red mini dress, maroon handbag and pink jacket all fall within the same color range. This is a great way to get the same chic effect as an all monochrome outfit, but without the stress of attempting to match all the elements of our outfit exactly.

Shop similar styles: Via Spiga Trench Coat ($200; $130); & Other Stories Mini Dress ($79; $28); Charles & Keith Kiss Lip Motif Bag ($83); Dr. Martens 1460 Smooth Boots ($170)

Something about combining a tailored suit and platform Docs gives us major Brit pop-punk vibes. Even more so if you opt for a colorful or patterned suit over traditional black or gray. Play up the rocker vibes with a loose tank or T-shirt and chain necklaces, or go the posh route with a button-up or crewneck knit.

Shop similar styles: Ann Taylor One-Button Blazer ($189) and Sophia Straight Pants ($118); Old Navy Tank Top ($10; $6); Dr. Martens Jadon Max Boots ($220)

If you want to go all in on Y2K and ‘90s favorites, a navy or burgundy boot will ultimately serve you better than black or white. The reason is that those alternate dark neutrals give your boots a softer edge and won’t look quite so costumey even when paired with bucket hats, pullover fleeces or even a Kurt Cobain-inspired tattered knit.

Shop similar styles: The Hat Depot Classic Cotton Bucket Hat ($12); Patagonia Synchilla Fleece Anorak ($149; $74); Halara Corduroy Pants ($40; $30); Dr. Martens Jaden Boots ($200)

Especially if you top it all off with a chic oversize sweater. Be sure to choose matte black leggings that leave no skin exposed (you can always add a pair of black socks to connect the top of your boot to the end of a cropped pair) for a more seamless, leg-lengthening look. As for your knit, opt for something that hits right about mid-hip to help maintain your proportions.

Shop similar styles: Theory Slouchy Turtleneck Sweater ($425; $128); Spanx Eco Care Seamless Leggings ($68); Dr. Martens 2976 Bex Boots ($270)

Classic Docs and an easy hoodie are perfect for casual Saturdays. But rather than wear them with other comfy basics, like leggings or sweatpants, swap in a silky midi skirt and leather jacket. The end result is a super chic ‘fit you can wear all weekend long.

Shop similar styles: Topshop Faux-Leather Jacket ($91; $73); Fila Valeria Hoodie ($50); Reformation Bea Skirt ($148); Dr. Martens 1460 Bex Boots ($180)

Prove that opposites really do attract by wearing classic black Docs with a polished, wide-leg trouser in a springy hue, like pale yellow or lavender. Just be sure to follow the Sandwich Dressing rule mentioned above and repeat either the black or the contrasting hue somewhere else within your ‘fit.

Shop similar styles: Levi’s OversizeDenim Jacket ($198; $107); Everlane Scoop-Neck Tee ($40); A&F Sloane Tailored Pants ($100); Calpak Luka Belt Bag ($58); Dr. Martens Jetta Boots ($200)

Dr. Martens will forever be intimately associated with ‘90s grunge, and wearing them with leather trousers only emphasizes that tough-gal vibe. However, throwing a preppy tweed jacket or plaid blazer into the mix is a great way to tone down some of that rock-and-roll feeling. We also highly suggest choosing a black topper; even though tweed and leather have seemingly opposite vibes, the shared black hue helps draw the two together.

Shop similar styles: Alice + Olivia Jayden Tweed Jacket ($595); Commando Faux-Leather Jogger Pants ($158); Dr. Martens Leona Boots ($190)

Who knew bike shorts and Docs could look so chic? Opt for shorts that are on the longer side and keep those casual vibes going with a crewneck sweatshirt and a belt bag for good measure. (P.S. If you prefer taller socks, try scrunching them down for a cute athleisure vibe.)

Shop similar styles: Anine Bing Leo Sweashirt ($180); L.L.Bean Pima Cotton Turtleneck ($35); Athleta High-Rise Bike Shorts ($59); Dr. Martens Sinclair Boots ($200)

Black jeans of just about any style look great with coordinating black Docs. And what goes better with black denim than a crisp white tee? Other than, you know, a white turtleneck, a white sweater, a white jacket—you get the picture. If you’re ever feeling overwhelmed with outfit planning, just take it back to the basics.

Shop similar styles: SAM Sherpa Denver Jacket ($395); Calvin Klein Uplift Turtleneck ($108; $33); Warp + Weft ASE Straight-Leg Jeans ($98); Dr. Martens Molly Boots ($200)

Remember in the early aughts when we all thought shorts and tights were the epitome of edgy fashion? Maybe not so much. We know Y2K is making a comeback, but we’d rather leave this combo behind in favor of more modern trends.

Honestly, we’d kind of say that denim minis, especially those with distressed hems, are across the board not a great idea. They feel far too juvenile and specific to Y2K, and we’ve yet to really see someone successfully modernize them for 2023. If you want to show off your legs, stick with more polished materials or a Mod minidress instead.