Not All Boots and Skirts Work Together, But These 6 Combinations Sure Do
From classic black skirts and cool biker boots to preppy pleated styles with sleek sock boots, here are six skirt-and-boot outfit ideas to copy this winter.
It felt like skirts were on the back burner for a minute there, but if you love them as much as I do, then I come bearing good news: spring/summer 2027 runways have spoken, and skirts are officially back in the fashion zeitgeist! The likes of Prada, Chanel, Miu Miu and Tommy Hilfiger all showcased several skirt trends set to dominate next season, and trust me when I say they’ll all make you want to pack away your jeans, shorts and tailored trousers to make room for these pretty styles.
Skirts dominated the spring/summer 2027 runways.
As someone who works in fashion (and takes their work seriously), I’ve made it my goal to get ahead of the pack and incorporate these chic skirt trends into my winter 2026 outfits. Of course, it’s too chilly to pair them with the open-toe heels and sandals spotted on the runway, so I decided to hunt for cool boot styles that pair well with them until the temperatures rise. And after hours of scrolling Instagram, Pinterest and TikTok, I managed to narrow it down to six ultra-sleek skirt-and-boot combinations to wear now and well into next season.
And the best part? I’ve rounded them up for you below. From classic black skirts worn with cool biker boots to give them some edge to preppy pleated midi skirts refined by minimalist sock boots, keep scrolling to discover the six skirt-and-boot outfit ideas to copy this winter. And rest assured: these pairings will put you firmly ahead of the pack, well before the skirt trends become big fashion players next spring/summer.
1. Pleated Skirt + Sock Boots
Style Notes: If you were savvy enough to hang onto your pleated midi skirts, even through the many years they were considered "dated", congratulations! This preppy trend is officially back for spring/summer 2027. Now, we all probably know that this elegant skirt style pairs well with pared-back shoes such as ballet flats and loafers, but if you really want to make yours look sleek this winter, look no further than the minimal leather sock boots. Not only are they a proportional dream when contrasted against the A-line silhouette of the pleated midi, but their refined nature will keep your outfits looking neat and polished no matter the price point you invest in.
Shop the Pairing:
This will go with everything your black midi skirt will.
Simple? Yes. But, so very easy to style.
Wear with jumpers, cardigans and button-down shirts alike.
Minimalists will love these.
2. White Skirt + Black Boots
Style Notes: Contrary to popular belief, white skirts are not just for spring and summer. It’s true; they do come into their own throughout the warmer months; however, there’s something that feels particularly fresh when worn with the darker palette we really lean on throughout autumn and winter. And the best boot style to pair them with? Classic black iterations, of course! This contrasting pairing comes with the unexpected appeal associated with an elevated outfit, but the two neutral hues remain wearable and well within the comfort zone of a minimalist like me.
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I want the entire outfit, please!
These are one of H&M's best-sellers. And for very good reason!
An easy way to freshen up your winter outfits.
Just so sleek.
3. Miniskirt + Riding Boots
Style Notes: I have to admit: miniskirts have always felt very hit or miss to me, someone who tends to stick to the more modest side of dressing. However, for winter 2026, I’ll be wearing the trusty shoe style that chic dressers have been relying on for years: riding boots. Of course, this pairing is not technically new, but it’s a foolproof combination that works every time, not only providing me with the coverage I prefer but also tapping into the "equestrian-chic" aesthetics that keep my winter outfits looking elegant and expensive.
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This also comes in versatile black and brown hues.
Equestrian-chic at its finest.
Wolford doesn't only make great tights.
If you already own a pair of black riding boots, try this sophisticated brown hue.
4. Wrap Skirt + Chunky Boots
Style Notes: With the ability to be dressed up or down with ease, if you don’t already own a wrap skirt, I’d highly recommend investing in one. Whilst linen and cotton fabrics come into their own when it's warm, until then you cannot go wrong with a thicker wool or jersey iteration that will keep you cosy from now until next spring. And the ideal boot to pair them with? A chunky style that will give this more refined silhouette an elevated touch. They’ll not only look incredibly considered when worn together, but the chunkier sole is a stylish way to ensure your feet are comfortable all day long.
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There's something so elegant about a knee-length skirt.
These look so comfortable.
I'd style this with a cream knit and the below boots.
The chunkier the sole, the better!
5. Check Skirt + Brown Boots
Style Notes: Typically a print we see throughout autumn/winter, I was shocked by the sheer amount of check and plaid skirts I spotted on the S/S 27 runways. Of course, as someone who very much leans into the dark academia aesthetic throughout the chiller months, I’m not in any way complaining, and I’ll be taking a cue from chic dressers and styling them with warm espresso-brown hues as a less harsh but no less versatile alternative to the black shoes I typically reach for around this time of year.
Shop the Pairing:
This has such a "dark academia" vibe to it.
Don't sleep on COS' designer-passing boots collection.
No one does preppy quite like Miu Miu.
I'm very into the subtly Western feel of these.
6. Black Skirt + Biker Boots
Style Notes: Timeless, versatile and so easy to style, black skirts aren't really a trend, but they are a staple that you’ll find on the runway year-round. And when the fashion girls want to give them some edge, they use cool biker boots to make their winter outfits look slightly more elevated. The perfect balance between a little edgy and extremely wearable, biker boots bring just the right amount of attitude to a classic black skirt.
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Karen Millen's winter collection is so good right now!
I'm obsessed with the lived-in feel these have.
So easy to dress up or down.
Everyone will think these are a designer find.
