Five Fashion Editor-Approved Ways To Wear Knee-High Boots In 2025

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Knee-high boots are an enduring wardrobe classic, loved as much by the Princess of Wales as they are by Rihanna. Like a trench coat and a classic black handbag, a pair of knee-high boots is considered a must-have to build out a capsule wardrobe, helping to streamline and simplify the getting-dressed process. But, unlike other pieces with such an enduring reputation, it can be more complicated to understand what to wear with knee-high boots as the style comes in so many varieties (and that’s before we consider the changing diktats coming from the catwalk, too).

That being said, there is a pair for everyone, and for every eventuality. How to style knee-high boots is a conundrum that can be answered by first considering the pair you either already have or are looking to invest in, as the perfect pairing changes depending on your personal style and the context in which you’re going to wear them.

Five Ways To Wear Knee-High Boots

A great pair of knee-high boots can be just as effective in elevating a winter walk look as they can be for taking a party dress into new territory (the official party season might have passed, but people do still have parties. Promise). So, here are five outfit ideas that show you how to wear five different
knee-high boots for an instant, achievable New Year-style success.

With A Mini Skirt

A knee-high boot with a mini skirt is a classic combination that is forever returning to the front of the trend cycle. Some ways of wearing an ultra-short skirt with a boot are reminiscent of the first pairing of the duo in the Sixties (modish mini, patent leather boots), while a more louche approach to the
silhouette (pleated kilt, block-heeled boots) will instantly evoke something more befitting of the nineties. In 2025, to make this pairing feel fresh for now, consider chunky boots that are packed with plenty of hardware, and styled with a puffball skirt that’s altogether dreamier. A fun T-shirt will elevate the
ensemble further.

With A Midi Skirt

A midi-skirt worn with knee-high boots brings instant polish and quick style credentials. In these proportions, it’s a printed boot or one with additional visual interest that will really come into its own as it’s revealed from under the longer-length skirt. Perhaps that leopard worn with a leather skirt, or
shining metallic with a black denim number. The combinations are endless.

With Denim Jeans

Admittedly, wearing knee-high boots with floor-skimming trousers might seem counterproductive as the majority of the shoe is hidden. But, in fact, it can offer a proposition similar to that of a midi-length skirt, bringing instant polish and flexibility. When it comes to this combination, extra thought is needed as you should choose a baggier jean that falls over the leg of the boot so it can’t quite be seen. For now, a low-block heel or entirely flat boot is the answer to avoid a look that feels too retro.

With Tucked-In Trousers

Giddy up! Isn’t remarkable that it has taken this long to mention anything of the equestrian connotations of knee-high boots? Well, here we are. This way to wear pulls straight from the paddock and onto the pavement with all the svelteness required for such equine pursuits. Choose skinny jeans
or slim-fit trousers that slide inside the knee-high boot with ease and elegance. Don’t think it is only riding-style boots that will do here, though. Look to Gabriette in Chloé for the cool-girl way to wear the look instead.

With A Party Dress

Dressing for a party might not be right at the top of your agenda right now, but it’s worth sharing the potential of knee-high boots worn in this context — and don’t think you have to go for full-sheer like Rihanna to make it work, either. A glossy boot (very Hedi Slimane) is an elegant alternative to a disco
heel that offers a subversiveness that is easy to wear. Just make sure that if you’re taking your boots out for a special occasion, they’re well-polished for a shining example of how to do it right.