7 Strong Winter Outfits Featuring Skirts and Boots

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. 

1. MINISKIRT + KNEE BOOTS

skirt-and-boot-outfits-285620-1639659257448-image

(Image credit: @MICHELLACCC)

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

2. CHECKED MIDI + SQUARE-TOE BOOTS

skirt-and-boot-outfits-285620-1639659257928-image

(Image credit: @SHHTEPHS)

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

3. SLIP SKIRT + SLOUCHY BOOTS

skirt-and-boot-outfits-285620-1639659257688-image

(Image credit: @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. 

4. SUEDE + LEATHER

skirt-and-boot-outfits-285620-1639659259103-image

(Image credit: @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). 

5. SKIRT + BOOTS IN A MATCHING COLOUR

skirt-and-boot-outfits-285620-1639659258784-image

(Image credit: @VIKILEFEVRE)

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

6. TWEED SKIRT + RUBBERISED BOOTS

skirt-and-boot-outfits-285620-1639659258251-image

(Image credit: @SYANALANIYAN)

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

7. KNITTED SKIRT + CHUNKY BOOTS

skirt-and-boot-outfits-285620-1639659256429-image

(Image credit: @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. 

Next Up, Spring/Summer 2023 Fashion Trends: The 21 Looks You Need to Know About

This story was published at an earlier time and has since been updated.

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over twelve years of experience in fashion journalism. She been creating engaging and elevated style content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories, and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, works closely with influencer talent on content initiatives, represents the brand at industry events, and regularly contributes to social media. Previously, Maxine appeared on TV in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o. 


Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship, she was offered a position on the Look magazine fashion desk. She accepted, leaving university a year early in the process. She went on to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion writer along the way. She later served as Look’s acting Editor in Chief before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others. Maxine works remotely from her countryside home near Edinburgh.