Not All Boots and Trousers Go Together, But These Combinations Always Work

Brittany Davy
As we head even further into winter, it's easy to feel like you've tried every single outfit combination in your wardrobe. With a reliable rotation of the same jeans and trousers being worn with various pairs of boots throughout the last few months, day-to-day dressing can seem like a repetitive task all to often.
Thankfully, with fashion weeks in London, New York and Paris all having taken place in the last couple of months, we've got plenty of new winter style inspiration, and we won't let a little bit of inclement weather stop us from having fun with our outfits. From innovative new formulas to tried-and-tested classic combinations, some of our favourite influencers have certainly proven that you don't need to buy an entirely new wardrobe to look fresh. All you need to do is think of new ways to wear your existing pieces together.
Whether it be tucking leggings into knee-high boots or embracing the versatility of tailored trousers, several trouser-and-boot trends have cropped up among the fashion set over the last couple of seasons. Even those who likely vowed to never wear leggings outside the gym again are now using them as a staple worn with their highest knee-high boots, and casual Chelsea boots are being given a new life when paired with cropped, structured trousers. My personal favourite? Tailored trousers with chunky ankle boots. After all, nothing makes a statement quite like a high/low mix.
Keep scrolling to see all of the boot-and-trouser combinations we're wearing now and to find where you can shop the very best.
These Are the 5 Best Boot-and-Trouser Combinations:
1. Chunky Boots + Tailored Trousers
Style Notes: A cropped tailored trouser allows the shoe to show, and avoids soggy hems on damp winter days. For a more elevated ensemble, look to a chunky-sole boot.
Shop the Look:
The perfect cropped trousers will fall a few inches above your ankle to make the most of chunky Chelsea boots.
Keep it smart with these sllek boots, and get extra points for a pared-back sole.
2. Knee-High Boots + Leggings
Style Notes: A classic combination that makes use of your perhaps forgotten leggings is the knee-high boots outfit formula. Take your comfy leggings from day to night by opting for a chic kitten-heel boot.
Shop the Look:
TeamBest Knockoff Luxury Clothing all agree: Reformation has some of the chicest footwear this winter.
The clever team at M&S have engineered leggings with Heatgen™ maximum warmth technology to keep you toasty all winter.
Other Stories knows good boots, and the riding boots come in black and brown for those looking for a wise investment purchase.
3. Ankle Boots + Wide-Leg Denim
Style Notes: Ankle boots will forever be timeless and pairing them with wide-leg jeans is a combo that will never go out of style.
Shop the Look:
This chocolate brown boot will never go out of style.
You can't talk about jeans without including Agolde's wide-leg pair.
4. Leather Trousers + Suede Boots
Style Notes: The only thing that could make a pair of leather trousers look even more chic is suede. Choose a pair of brown suede boots to contrast you black leather trousers if you want to score serious style points.
Shop the Look:
5. Biker Boots + Straight Jeans
Style Notes: Jeans remains a key feature of our wardrobes all year round, but for winter 2024, we've noticed fashion people are styling them with biker boots to give them an edgier feel.
Shop the Look:
Opt for a lighter-wash to freshen up your winter outfits.
Biker boots are for everyone, from the statement dresser who wants to stand out from the crowd, to the minimalist look to add interest to their outfits.
If our editor's reviews are anything to go by, these are a reliable pair of high-street jeans you'll wear for years to come.
For those not fully sold on classic moto boots, try this subtle pair with a little biker energy.
This story was published at an earlier time and has since been updated.
Remy Farrell is a London-based fashion editor with 10 years of experience covering fashion, beauty and lifestyle. After graduating with a journalism degree and working on the fashion teams for titles such as Grazia, Elle, and British Vogue, she moved into the luxury e-commerce sector, working as fashion assistant at TheOutnet.com After expanding an assisting and styling portfolio that includes talent such as Gigi Hadid, Victoria Beckham and Miquita Oliver, she ventured into beauty, compiling reviews and diverse beauty content. In her role as fashion editor atBest Knockoff Luxury Clothing , Remy is interested in discovering new brands to share with the WWW UK readership, and loves uncovering hidden gems to make shopping accessible to everyone.
- Brittany DavyEditorial Assistant
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