It felt like skirts were on the back burner for a minute there, but if you enjoy wearing them as much as I do, then I come bearing good news: spring/summer 2027 runways have spoken and skirts are officially back on the map. Not only that, they’re dominating it. Prada, Chanel, Miu Miu and Tommy Hilfiger all showcased a number of the skirt trends that will each prove to be very big deals next year, and trust me when I say they’ll all make you want to pack away your jeans and tailored trousers (at least temporarily) to make room for some swish.
Skirts dominated the spring/summer 2027 runways.
(Image credit: Chanel, Tommy Hilfiger, Prada, Miu Miu S/S 2027 – Launchmetrics Spotlight)
As someone who works in fashion (and takes their work very seriously), I’ve made it my mission to get ahead of the pack and incorporate these chic skirt trends into my winter 2026 outfits. Of course, it’s currently too chilly to pair them with the open-toe heels and sandals that were spotted on the runway, so instead, I decided to go on the hunt for the cool boot styles that will pair well with them until temperatures rise. After hours of scrolling on Instagram, Pinterest and TikTok, I managed to narrow my attention down to six skirt-and-boot formulas that work better than the rest and that you’ll genuinely want to wear from now and well into the next season.
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-boots outfit ideas to try this winter.
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6 Skirt-and-Boot Outfits to Try in 2026
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:
prada
Pleated silk midi-skirt
This will go with everything your black midi skirt will.
& Other Stories
Leather Sock Boots
Simple? Yes. But, so very easy to style.
Boden
Aya Cotton Sateen Midi Skirt
Wear with jumpers, cardigans and button-down shirts alike.
A.Emery
Sutherland Leather Ankle Boots
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 myself.
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I want the entire outfit, please!
These are one of H&M’s bestsellers. And for very good reason!
ZARA
Contrast Flowing Skirt
An easy way to freshen up your winter outfits.
3. Mini Skirt + Riding Boots
Style Notes: I have to admit, mini skirts have already felt very hit or miss to me, as 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 each and every time, not only providing me with the coverage I prefer but also tapping into the ‘quiet luxury’ and ‘equestrian-chic’ aesthetics that keep my winter outfits looking elegant and expensive.
Shop the Pairing:
Reformation
Carla Low Waist Skirt
This also comes in versatile black and brown hues.
Equestrian-chic at its finest.
Wolford doesn’t only make great tights.
Massimo Dutti
Leather Riding Boot
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 as temperatures start to rise, 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 that your feet remain comfortable all day long.
Shop the Pairing:
St. Agni
Leather Everyday Wrap Midi Skirt
There’s something so elegant about a knee-length skirt.
These look so comfortable.
Uniqlo
Double-Faced Wool Blend Mini Skirt
I’d style this with a cream knit and the below boots.
ASOS DESIGN
Ashton Chunky Chelsea Boots
The chunkier the sole, the better!
5. Check Skirt + Brown Boots
Style Notes: Typically a print we see throughout autumn and winter, I was shocked by the sheer amount of check and plaid skirts I spotted on the spring/summer 2027 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.
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This has such a “dark academia” vibe to it.
Don’t sleep on COS’ designer-passing boots collection.
Miu Miu
Pleated Checked Flannel Miniskirt
No one does preppy quite like Miu Miu.
Free People
Daisy Slouchy Kitten Heel Boots
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 feeling alternative and extremely wearable, biker boots bring just the right amount of attitude to a classic black skirt.
Shop the Pairing:
karen millen
Faux Suede Pencil Skirt
Karen Millen’s winter collection is so good right now!
PARIS TEXAS
Roxy 45 Studded Leather Knee Boots
I’m obsessed with the “lived-in” feel these have.
TOMMY HILFIGER
Premium Knit Slim A-Line Midi Skirt
So easy to dress up or down.
ASOS DESIGN
Cassandra Eyelet Biker Boots
Everyone will think these are a designer find.
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