Seasonal Fashion
Dec 5, 2022

7 Strong Winter Outfits Featuring Skirts and Boots

by Maxine Eggenberger

When you're tired of wearing your jeans (and, let's face it, your joggers) on loop, what should you wear? I can tell you that this has been a hot topic of discussion on the Who What Wear UK Slack channel this week, especially with the new season coming into view. There was talk of new colour trends, the pieces French women always reach for and the coat that always looks so expensive (no matter how much you've spent on it). But the one thing we all settled on as a great look that works for now and spring is the classic skirt-and-boot combo.

Right now, the skirt needs to say "I'm ready for 2023," but the footwear needs to say, "Do you realise that it's still winter?" And trust us—the look is so easy to adapt. Whoever you are and whatever your personal style, there's a skirt-and-boot pairing out there for you. Whether you wear an eternally chic pleated skirt with heeled knee-high boots or prefer to prioritise comfort, you can't really go wrong.

For inspiration, we looked to some of our fashion friends who have been wearing this fail-safe combo on repeat. Keep scrolling for some much-needed winter-dressing ideas and to shop any key pieces you might not already have in your wardrobe to achieve these 'fits.

Skirt and Boot Outfits: @MICHELLACCC

Photo:

@MICHELLACCC

Style Notes: Cancel out the chill when wearing a trending miniskirt with a pair of knee-grazing boots.

& Other Stories Tailored Mini Skirt

& Other Stories

Tailored Mini Skirt

At this point a black mini is a staple.

Jigsaw Talley Knee High Leather Boots

Talley Knee High Leather Boots

These boots are on every editor’s wish list.

Skirt and Boot Outfits: @SHHTEPHS

Photo:

@SHHTEPHS

Style Notes: Checked skirts are a fashion classic—bring them up-to-date with a pair of of-the-moment square-toes.

Khaite Maddie Ribbed Knit Sweater

Maddie Ribbed Knit Sweater

The jumper silhouette that’s dominated for three years now.

Brora Wool Blend Check Skirt

Wool Blend Check Skirt

Tartan always comes back in style.

H&M Heeled Boots

These boots look so expensive.

Skirt and Boot Outfits: @SASHA.MEI

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@SASHA.MEI

Style Notes: Get more wear out of your slip skirts with a pair of slouchy heeled boots—this combination of teal and ecru is beautiful.

Aligne Gila Velvet Blazer

Gila Velvet Blazer

Trust us—you’ll wear this velvet blazer more than you think.

Reiss Florie Midi Slip Skirt

Florie Midi Slip Skirt

The perfect shade of teal.

Sosandar Leather Stiletto Knee-High Boots

Leather Stiletto Knee-High Boots

Another excellent high-street boot option.

Skirt and Boot Outfits: @CHAMPAGNEMANI

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@CHAMPAGNEMANI

Style Notes: For a cosy texture combination, try wearing a suede-finish skirt with a pair of leather boots (a cashmere cardigan won’t hurt either).

Jigsaw Maldow Zip Leather Boots

Maldow Zip Leather Boots

The square top is a nice touch.

Skirt and Boot Outfits: @VIKILEFEVRE

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@VIKILEFEVRE

Style Notes: Create an elevated aesthetic by matching the colour of your skirt to that of your boots, like this chic navy example.

Chloé Belted Virgin Wool-Twill Midi Skirt

Belted Virgin Wool-Twill Midi Skirt

Up there as one of the most elegant skirts we’ve seen.

LK Bennett Camelia Black Stretch Suede Ankle Boots

Camelia Black Stretch Suede Ankle Boots

Sock boots are ideal for dressing up jeans, too.

Skirt and Boot Outfits: @SYANALANIYAN

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@SYANALANIYAN

Style Notes: Give your more formal skirting a cool overhaul with the addition of rubberised boots—knee-high for minis, ankle for midis.

Karen Millen Tweed Gold Button Cropped Jacket

Tweed Gold Button Cropped Jacket

We keep coming back to this tweed co-ord.

H&M Knee-High Boots

Knee-High Boots

We had to do a double take when we saw the price of these boots.

Skirt and Boot Outfits: @EMMAROSESTYLE

Photo:

@EMMAROSESTYLE

Style Notes: If staying cosy and comfy is of the utmost importance, do so in a pair of chunky leather boots and a knitted skirt—we promise it’s just as comfortable as your joggers.

Arket Cotton Wool Jumper

Cotton Wool Jumper

A knit we know is going to fly.

Altuzarra Rozey Ribbed Stretch-Knit Midi Skirt

Rozey Ribbed Stretch-Knit Midi Skirt

Because who wouldn’t want this in their wardrobe?