Everyone needs at least one pair of knee-high boots in their sartorial arsenal, especially now we’re in peak boot-wearing weather. Sure, ballet flats and loafers – both big autumn shoe trends, FYI – are great transitional footwear options, as are our ever-reliable fashion trainers. But, when it comes to getting maximum wear out of all the dresses and skirts hanging in your wardrobe, nothing beats a boots and dress combo.
Knowing how to style your knee-highs with dresses is a whole other matter, though. Should the hem of your dress cover your boots? Or, should there be some skin peeking – and if so, how much? Would it look weird if my dress is fitted but my boots are slouchy? Can you wear leather boots with a leather jacket, or will I look like a character from The Matrix?
We get it, this situation can be v confusing! As much as we love ’em, knee-high boots aren’t always the easiest to style. Luckily, the street style set has you covered when it comes to outfit inspo. And, to make getting dressed this autumn winter even easier, we’ve recreated these exact lewks for you so you can shop with a single click. Because while you definitely need one pair of knee-high boots, no one said you can’t have more.
Pair a denim dress with brown suede boots
Speaking of must-haves, a denim dress (or maxi skirt) is definitely up there. A long-sleeve midi version is ideal for colder temperatures, but if you have a sleeveless summer style you could try layering it over a roll-neck for added warmth. Then, simply add a pair of knee-high boots to complete the look. While denim works with almost everything, we love the warmth that camel-hued boots bring. Also, use this as evidence that the hem of your dress can skim the top of your boot and still be super cute!
Shop denim dress + knee high boots:
La Redoute Signatures Suede Knee-High Boots with Block Heel
Now 30% Off
Aligne Parsons Denim Midi Dress
Now 22% Off
Jones Bootmaker Lou LouS Slim Calf Knee High Suede Boots
Opt for a slit
An easy way to highlight your boots, because after all they are the star of the show here, is by opting for a dress with a leg slit. How high you go is up to you, even a small slit will still show off your footwear with every step. We love how these black leather block-heel boots instantly dress up a casual, short-sleeve black dress.
Shop slit dresses + knee high boots:
ASOS DESIGN Ultimate Midi Tea Dress with Collar
Aldo Nevada Leather Knee High Boots
Friends Like These Puff Sleeve Ruched Waist V Neck Midi Dress
Go grunge
One thing we love in fashion is juxtaposition. A romantic slip dress somehow always works with biker boots. When you wear this out on date night, you’ll be feelin’ yourself and you won’t have to worry about your feet hurting! Win-win.
Shop Romantic-Grunge:
Dune London Totoe Buckle Detail Leather Knee-High Boots
New Look Pink Satin Scoop Neck Maxi Slip Dress
Now 29% Off
Stradivarius Flat Distressed Boots with Buckles
Make it a mini moment
If you really wanna steer clear of the whole which-hemline-looks-best-with-knee-length boots convo, then maybe mini dresses and skirts are more your speed. In particular, a wrap style with cowboy boots might speak to your wild side!
Shop mini dress + knee high cowboy boots:
Pretty Lavish Textured Wrap Mini Dress
Now 75% Off
ASOS DESIGN Camden Flat Western Boots
Zara Short Dress with Bows
Fancy, fun hemlines are a big yes!
We can’t think of a better way to bring even more attention to your boots than by adding a statement hemline to your look. Whether you opt for feathers or fringing, the movement will instantly draw the eye. Cue compliments flooding yours – and your boots’ – way!
Shop fringe dress + knee high boots:
Na-Kd Knee High Croc Boots
Simply Be Cream Fringe Knitted Midi Dress
Now 27% Off
Sosandar Chocolate Brown Croc Leather Knee High Boot
Double leather *does* work
Going full leather is not not a look – Matrix chic is a thing after all. But if you want to avoid Keanu Reeves comparisons, there are some rules you should follow. Whether you’re wearing a leather jacket, dress, skirt or trench coat, ensure your outfit includes other textures to break it up a little. Yes, you can coordinate the colours of your leather pieces, but why not try injecting some contrast like a croc effect knee-high boot? Again, this will visually break up your outfit. Don’t forget to layer on the jewellery and you’re onto a winner.
Shop leather + knee high boots:
Silence + Noise Faux Leather Trench Coat
Now 30% Off
Charles & Keith Louise Block-Heel Knee-High Boots – Black
Mango Short Leather-Effect Dress
Try colour-coordinating
For a really statement ensemble, opt for a pair of look-at-me red knee-high boots and a coordinating red dress. Finding a patterned dress, no matter how subtle, will help make matching up your hues that little bit easier. The A-list has been telling us for quite a while now that the only way to wear red is head-to-toe, maybe it’s time we try it for ourselves.
Shop colour-coordinating dress + knee high boots:
Duo Boots Freya Knee High Boots in Red Leather
Warehouse Satin Georgette Panelling Asymmetric Hem Midi Dress
Now 20% Off
Boden Heeled Leather Knee Boots
Limit your look to one animal print item
We love leopard print as much as the next girl, but unlike leather, you can go overboard if you wear a leopard print dress *and* leopard print boots. Instead, stick to black boots when you’re wearing animal print clothing and vice versa – a neutral, block colour outfit if you’re repping leopard print boots.
Shop leopard print dress + knee high boots:
Damson Madder Bluebelle Midi Dress
New Look Stone Leopard Print Knee High Boots
Sister Jane Lola Leopard Jacquard Dress
Tarah-Lynn Saint-Elien is the fashion editor at Cosmopolitan, writing weighty and witty stories that run the gamut of gushing over Zendaya to convincing you of everything you need in your closet! She began her journey in the industry with a fashion and faith blog and an internship at Elle.com almost 10 years ago. Since then, she’s also served as the style editor at The Haitian Times. The Haitian-American pageant queen is a Syracuse Masters graduate and the author of two books, including: Claim Your Crown. Follow her on Instagram and Twitter: @iamtarahlynn.
Alexandria Dale is Digital Fashion Writer at Cosmopolitan & . Covering everything from the worth knowing about to the latest fashion news, there’s nothing she loves more than finding a high street dupe of a must-have designer item. As well as discovering new brands, she’s passionate about and establishing the trends that are actually worth investing in. Having worked in fashion journalism for six years, she has experience at both digital and print publications including Glamour and Ok!