Everyone needs at least one pair of knee-high boots in their fashion arsenal. Especially now is the peak season for wearing boots. Indeed, ballet flats and loafers (both big fall shoe trends) are great transitional footwear options, as are the ever-reliable fashion trainers. But to make the most of all the dresses and skirts in your wardrobe, there’s nothing better than pairing boots with dresses.
However, knowing how to style knee highs with a dress is a completely different matter. Should the hem of the dress cover the boots? Or should some skin peek through? If so, how much? Does it look weird if the dress is snug but the boots are slouchy? Leather on a leather jacket Can you wear boots or look like a character from The Matrix?
I understand. This situation can be confusing. We love knee-high boots, but knee-high boots aren’t always easy to style. Luckily, the street style set has your outfit inspiration covered. And to make dressing this fall/winter even easier, we’ve recreated these exact leaks for you to shop with just one click. Because while you definitely need a pair of knee-high boots, no one said you can’t have more than that.
Combine a denim dress with brown suede boots
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When it comes to must-haves, a denim dress (or maxi skirt) is definitely up there. The long-sleeved midi version is perfect for colder temperatures, but if you have a sleeveless summer style, you can also layer it over a roll neck for extra warmth. Then just add knee-high boots to complete the look. Denim goes with almost everything, but I love the warmth that camel-colored boots bring. Also, use this as proof that it’s still super cute even if the hem of your dress grazes the top of your boots.
Shop Denim Dress + Knee-High Boots: La Redoute Signatures Suede Knee-High Boots with Block Heel
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Credit: La RedouteAligne Parsons Denim Midi Dress
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Credit: AligneJones Bootmaker Lou LouS Slim Calf Knee High Suede Boots Credit: Jones Bootmaker
choose a slit
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Boots are the star of the show here, so an easy way to highlight them is to choose a dress with a leg slit. How high you go is up to you, and even a small slit will make your feet look great with every step. We love how these black leather block heel boots instantly dress up a casual short sleeve black dress.
Buy Slit Dress + Knee High Boots: ASOS DESIGN Ultimate Midi Tea Dress with CollarCredit: ASOSAldo Nevada Leather Kne High Boots
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Credit: AldoFriends Like These Puff Sleeve Ruched Waist V-Neck Midi Dress Credit: Next
go grunge
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One of our favorite things about fashion is juxtaposition. Romantic slip dresses somehow always go with biker boots. Wear these on a date night to feel good and not have to worry about sore feet. It’s a win-win.
Shop Romantic Grunge: Dune London Tote Buckle Detail Leather Knee High Boots Credit: Dune London New Look Pink Satin Scoop Neck Maxi Slip Dress
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Credit: New LookStrADIvarius Flat Distressed Boots with Buckles Credit: Stradivarius
Let’s make it a little moment
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If you really want to avoid the debate over which hemline looks good with knee-high boots, a minidress or skirt might be a faster option. In particular, a wrap style paired with cowboy boots might reveal your wild side!
Shop Mini Dress + Knee High Cowboy Boots: Pretty Lavish Textured Wrap Mini Dress
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Credit: ASOSASOS DESIGN Camden Flat Western Boots Credit: ASOSZara Short dress with bow Credit: Zara
Fancy and fun hemlines are welcome!
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What better way to draw more attention to your boots than by adding a statement hemline to your look? Whether you choose feathers or fringe, the movement will instantly catch the eye. Cue lots of compliments for you and your boots!
Buy Fringe Dress + Knee High Boots: Na-Kd Knee High Croc Boots Credit: Na-KdSimply Be Cream Fringe Knitted Midi Dress
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Credit: Simply BeSosandar Chocolate Brown Croc Leather Knee High Boots Credit: Sosandar
Double leather *works*
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Going full leather is not just about looks. Matrix chic is what it’s all about, after all. However, if you want to avoid comparisons to Keanu Reeves, there are some rules to follow. Whether you’re wearing a leather jacket, dress, skirt, or trench coat, make sure it includes other textures to add a little break to your outfit. Yes, you can play with the color of the leather pieces, but why not add some contrast, like knee-high croc boots?Again, this visually disrupts the outfit. Don’t forget to layer your jewelry. Then you’re a winner.
Buy Leather + Knee High Boots: Silence + Noise Faux Leather Trench Coat
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Credit: Urban OutfittersCharles & Keith Louise Block Heel Knee High Boots – BlackCredit: Charles & KeithMango Short Leather Effect Dress Credit: Mango
Try color coordinating
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For a truly statement-making ensemble, opt for look-at-me red knee-high boots and a coordinating red dress. No matter how delicate, finding a patterned dress will make color matching a little easier. The A-listers have been telling us for quite some time that the only way to wear red is from head to toe. Perhaps it’s time for us to try it ourselves.
Shop Color Coordinating Dress + Knee-High Boots: Duo Boots Freya Knee-High Boots (Red Leather) Credit: Duo BootsWarehouse Satin Georgette Paneling Asymmetric Hem Midi Dress
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Credit: WarehouseBoden Heel Leather Knee Boots Credit: Boden
Wear just one animal print item
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We love leopard print as much as the next girl, but unlike leather, wearing a leopard dress *and* leopard print boots can be too much. Instead, wear black boots when wearing animal print clothing, and vice versa, wear neutral block colors when wearing leopard print boots.
Shop Leopard Print Dress + Kne High Boots:Damson Madder Bluebelle Midi DressCredit: Damson MadderNew Look Stone Leopard Print Kne High BootsCredit: New LookSister Jane Lola Leopard Jacquard DressCredit: Sister JaneRelated Stories
Tara-Lynn Saint-Therian is Cosmopolitan’s fashion editor and writes stories with weight and wit that make you think of Zendaya and everything you need in your closet. She began her journey in the industry nearly 10 years ago with a fashion and faith blog and an internship at Elle.com. Since then, she has also served as the style editor of the Haiti Times. The Haitian-American pageant queen is a graduate of the Syracuse Master’s program and the author of two books, including “Claim Your Crown.” Follow her on Instagram and Twitter: @iamtarahlynn.
Alexandria Dale is a digital fashion writer at Cosmopolitan & Women’s Health UK. Covering everything from celebrity style moments worth knowing to the latest fashion news, there’s nothing she loves more than finding high-street camo for must-have designer pieces. As well as discovering new brands, she is passionate about sustainable fashion and establishing trends that are actually worth investing in. She has worked in fashion journalism for six years, with experience at both digital and print publications such as Glamor and Ok!
