Not All Boots and Skirts Work Together, But These 6 Combos Do

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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.

a model wearing a check Chanel skirt, a model wearing a white maxi Tommy Hilfiger skirt, a model wearing a black pleated Prada skirt, a model wearing a check Miu Miu skirt on the S/S 2027 runways — *Skirts dominated the spring/summer 2027 runways.*

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.

6 Skirt-and-Boot Outfits to Try in 2026

1. Pleated Skirt + Sock Boots

@frannfyne and @mcristinastyling wearing black pleated skirts and black leather sock boots, @brittanybathgate and @ebonylouisefrancis wearing dark grey pleated skirts and black leather 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

prada

Pleated silk midi-skirt

Leather Sock Boots - Black

& Other Stories

Leather Sock Boots

Aya Cotton Sateen Midi Skirt-Black

Boden

Aya Cotton Sateen Midi Skirt

Sutherland Leather Ankle Boots

A.Emery

Sutherland Leather Ankle Boots

2. White Skirt + Black Boots

@modedamour. @nnennaechem, @thevisuelofgrace, @erinoffduty wearing white long skirts with black leather 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.

Shop the Pairing:

Dipped Knit Skirt White - Xxs

H&M, Knee-High Boots

Zw Collection Contrast Flowing Skirt - Oyster-White - Xs

ZARA

Contrast Flowing Skirt

Capucine Booties in Smooth Leather

3. Mini Skirt + Riding Boots

@maryljean wearing a brown mini skirt, @rabia.cissokho wearing a burgundy mini skirt, @emmanuellek_ wearing a tan mini skirt, @kristincabat wearing a cream mini skirt with 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:

Carla Low Waist Skirt

Reformation

Carla Low Waist Skirt

Leather High Boots - Women | Mango United Kingdom

Midnight Grace High-Rise Jersey Miniskirt

Massimo Dutti, Leather Riding Boot

Massimo Dutti

Leather Riding Boot

4. Wrap Skirt + Chunky Boots

@modedamour wearing a brown midi wrap skirt, @alexisforeman wearing a black midi wrap skirt, @francescasaffari wearing a mini wrap skirt, @taffymsipa wearing a check midi wrap skirt with 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.