The ultimate guide to styling knee-high boots with dresses this season

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We love these knee-high boots and dress combos!Edward Berthelot - Getty Images

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

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Christian Vierig - Getty Images

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!

Opt for a slit

street style september 2024 new york fashion week
Christian Vierig - Getty Images

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

street style september 2024 new york fashion week
Edward Berthelot - Getty Images

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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Christian Vierig - Getty Images

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!

street style september 2024 new york fashion week
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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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Edward Berthelot - Getty Images

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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Edward Berthelot - Getty Images

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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