Posted on: November 15, 2023 Posted by: Comments: 0

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 Copenhagen, 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, fashion editors and street style stalwarts 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 tailored suit trousers into mid-calf boots or embracing the versatility of skinny jeans, several trouser-and-boot trends have cropped up among the street style set over the last couple of seasons. Even those who likely vowed to never wear skinnies 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 mid-calf 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. 

Style Notes: A cropped trouser allows the shoe to show, and avoids soggy hems on damp winter days. 

The perfect cropped trousers will fall a few inches above your ankle to make the most of chunky Chelsea boots.  

A cult favourite. 

Style Notes: For a more elevated ensemble, look to cropped smart trousers and a heeled boot. 

Skinny suit trousers make a cropped hemline feel office-ready. 

Keep it smart with pointed leather boots, and get extra points for a wearable heel. 

Style Notes: Tailoring remains a key feature of our winter wardrobes, and we’ve noticed fashion people are styling theirs tucked into mid-calf boots. 

If our editor’s reviews are anything to go by, these are a reliable pair of trousers you’ll wear for years to come.

Stand tough in a pair of lace-up boots with attitude. 

Style Notes: Add contrast to slick tailoring with chunky boots. 

Opt for a slouchy silhouette for a contemporary feel. 

Ganni’s iconic mid chelsea boots come in 8 variations. 

Style Notes: A classic combination that makes use of your perhaps forgotten skinny jeans is the knee-high boots outfit formula. 

A sculpting, stretchy fit that hugs the leg all the way down to the ankle. 

Team Who What Wear all agree: Massimo Dutti has some of the chicest footwear on the high street. 

Style Notes: Take your skinny jeans from day to night with this boot pairing. 

The clever team at Good American have engineered jeans with a contoured waistband to get rid of that annoying gap at the back. 

Russell & Bromley knows good boots, and the Paris comes in black, suede and snake for those looking for a wise investment purchase. 

Style Notes: The cowboy boot revival is showing no signs of slowing down. 

It’s easy to see why Levi’s 501 jeans remain a fashion favourite. 

For those not fully sold on classic cowboy boots, try these subtle suede boots with a little Western energy. 

Style Notes: Chrissy proves that you wardrobe staples can have a brand new feel with the addition of a great pair of shoes. 

You can’t talk about jeans without including Agolde’s stovepipe jeans. 

Ready, boots? Start walking. These are cowboy boots for the statement dresser who looks for styles that stand out from the crowd. 

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

Next Up: It’s Boot Season, and These Are the Trends That Will Dominate

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