4 Chic Leggings-Boots-and-Jumper Outfits I'll Live in This Winter

Sometimes it's the simplest outfit pairings that end up being the most impactful. Take the humble jeans-and-a-nice top combination, which we turn to for almost every night out. Then there's black trousers and a Breton stripe—on paper, it mightn't sound all that exciting, but in reality, it works and doesn't look in the slightest bit try-hard. And isn't that what we all want? To look stylish but with minimal effort? I know I do. So with the idea of stripping back my outfits to basics, I thought to myself, What is the simplest outfit pairing I can wear this season? The answer: some leggings, a jumper and boots. 


(Image credit: @NLMARILYN)

More comfortable than jeans and with the ability to look incredibly sleek, leggings shouldn't be overlooked when assembling your trans-seasonal outfits; they form a solid base to set interesting separates against and are pretty low-maintenance in terms of upkeep and cleaning. Then there are jumpers; find the right one, and you'll be cosy and chic-looking in equal measure. And finally, there are boots. From knee-high pointed-toe styles to chunky, track-sole ankle grazers, there's a boot trend for every aesthetic and outfit mood. 

Put these formidable staples together and what do you get? An impressively stylish and genuinely easy outfit suggestion. I can do one better—I've created four shoppable graphics that showcase just how effective legging-jumper-and-boot outfits can be. Scroll on to see them. 



(Image credit: WHO WHAT WEAR UK)

Style Notes: Cable knitwear might be classic, but the interesting weave calls for a more basic legging style. Ribbing, for example, runs the risk of pulling focus. You could, however, add more fanciful boots; personally, I always think mock-croc looks the premium part. When temperatures dip, add a blazer into the equation. 

Shop the Look:



(Image credit: WHO WHAT WEAR UK)

Style Notes: Striped knitwear is having a major moment, but that doesn't mean it's tethered to this season—this is a jumper style you'll wear forever, so a designer option wouldn't be a bad investment. I think H&M's panelled leggings help to elevate the entire ensemble—even when casual items like a beanie and tall Chelsea boots come into play. 

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(Image credit: WHO WHAT WEAR UK)

Style Notes: Red knitwear is just as long-lasting than cream or black styles, but it feels particular current now, as fashion people keep adding pops of it in their outfit. Sure, this jumper is sans sleeves but it still checks the knitwear box, and will layer under all of your coats seamlessly. 

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(Image credit: WHO WHAT WEAR UK)

Style Notes: You cannot go wrong with a grey jumper. The classic colour and shape needed a modern twist and I had a hunch that adding some split-hem leggings would work. I love it when I'm right. Add a pair of pointed-toe boots, and you'll look like you have legs for days. 

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Next Up, The Autumn/Winter 2023 Fashion Trends That Really Matter

This story was originally 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 thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically 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, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning 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 at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.