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 in 2025, FYI – are great transitional footwear options, as are our ever-reliable 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 to make getting dressed this autumn/winter even easier. While you definitely need one pair of knee-high boots, no one said you can’t have more.
Everyone’s clicking on…Pair a denim dress with brown suede boots
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Speaking of must-haves, a denim dress (or maxi skirt) is definitely up there. A long-sleeve midi version is ideal for colder temperatures, or layer a sleeveless summer style 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 brown suede 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!
Opt for a slit 
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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.
Go grunge
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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.
Make it a mini moment
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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!
Fancy, fun hemlines are a big yes!
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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!
Double leather *does* work
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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.
Try colour-coordinating
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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.
Limit your look to one animal print item
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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.
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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 about 10 years ago. Since then, she’s also served as the style editor at The Haitian Times. The Haitian-American pageant queen is Miss Supranational Haiti 2024, a Syracuse Masters graduate, and the author of three books, including: Claim Your Crown. Follow her on Instagram and TikTok: @iamtarahlynn.
Alexandria Dale is the Digital Fashion Writer at Cosmopolitan UK. Covering everything from the celebrity style moments 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 sustainable fashion 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!