Any trouser-phobe will tell you that skirts aren’t only for summer; they open up a world of styling opportunities come winter, too. All you need are the perfect boots to pair with them.
This season, however, it seems there are more boot options to choose from than ever before—hiker, thigh-high, combat, lace-up, Western, to name but a few—which in turn makes deciphering which styles look best with which outfits all the more difficult. So shifting our focus back to the aforementioned skirt, we decided to uncover the best boots to wear with skirts, with a little help from some of our fashion friends.
Keep scrolling to see eight flawless boot-and-skirt pairings. Then, proceed to shop everything you need to re-create the look for yourself.
Style Notes: While leather boot styles work just as well with short skirts, there’s no denying that the proportions of a maxi skirt can add the cool factor.
Who knew a denim skirt could look so cool.
Invest in a great pair of boots now and they will see you through many years, from day to night.
These are just stunning, don’t you think?
The studding adds a edgy look and I’m here for it.
Style Notes: Slouchy, knee-high boots look excellent with just about every skirt length, but they look their best with a miniskirt, as evidenced by Ada Oguntodu. Add sheer tights if you prefer more coverage.
Wear with camel, black, grey, white… The choices are endless.
This dark chocolate colour is everywhere at the moment.
The pull on detail is key here, meaning you can slouch them as much or as little to your hearts desire.
The perfect amount of slouchiness.
Style Notes: Key details, such as lace-up fronts, are too pretty to be covered up by long trousers. Instead, pair them with a split-front or wrap skirt like Katherine Ormerod did to show them off to great avail.
The high waist detail is so flattering.
I’m sorry but these are just too good.
Crafted in Spain from butter soft leather , these boots are an investment that you will bring out year after year.
I’ve always been a fan of Hobbs accessories. These wont stick around.
Style Notes: Much like suede, white and ecru tones offer a softer boot alternative to that of the often-favoured black-leather styles. We love how Marissa Cox wears her white ankle boots with black opaque tights.
This skirt is crafted from the softest suede. Wear with a chunky jumper or a tee and blazer.
I’m obsessed with the square toe on this style.
If your’e a fan of a calf length silhouette then these should be on your radar.
These look so high end IRL.
Style Notes: Combat boots are a wonted staple, and lately, fashion types have been wearing the grunge footwear with their more summery pieces to pull them into the right season. Case in point: Tamara Mory’s slip-skirt-and-chunky-boot pairing.
I love a pop of lilac in my winter wardrobe.
I’m obsessed with the chunky platform on these DM’s, so cool.
These are such a great price and will go with so many other winter outfits.
The OG combat boots.
Style Notes: For some skirts, structured boots can look too chunky. In this instance, turn your attention to sock-style boots that fit tightly around the ankle to create a streamlined leg silhouette. Case in point: Ellie Delphine’s neoprene pair.
This monochrome design can easily be dressed up or down.
I love a chunky mid-sized heel, which always feels chic yet comfortable.
This luxe version is made from stretchy suede to give the sock-like fit, clever eh.
It’s the square toe that elevates the whole boot for me.
Style Notes: Western boots look cool with just about anything you throw at them, though miniskirts, much like Imani Randolph’s, offer an unexpected and modern alternative to prairie dresses and blue denim.
A white mini is surprisingly versatile. We’d wear ours with neutral tones like Imani, but you could also style with bright colours, too.
OK now I want to wear silver cowboy boots with everything I own.
If you’re on the hunt for a designer style that will stand the test of time, voila.
Everything you could ever want from a cowboy boot.
Style Notes: It would be remiss not to mention this year’s It boots, chunky lug-soled boots. Although they look great with everything from jeans to dresses, we think slip skirts balance out their cumbersome proportions perfectly—as does Francesca.
Wear now with a chunky cardigan and then come spring pair with a printed t.shirt and khaki shacket.
I can vouch for just how comfy these are.
A chic alternative to classic black.
Classic Chelsea boots for under £100? *Adds to basket.*
