Whilst winter comes with its fashion struggles, it does offer a moment to indulge in one of my favourite styling combinations: boots and dresses. Bored of wearing trousers all the time, I’ve been looking for the opportunity to re-introduce dresses to my wardrobe rotation. With this in mind, it’s time to debut my favourite outfit combination.
I’m keen to add tights to my outfit rotations but for now, I don’t need a layer quite so heavy, so I find myself reaching for knee-high boots specifically for this purpose. Not only are they the most polished boot silhouette (in my opinion), but they’re also totally timeless and work well with every dress trend I can think of. For midis, they disappear under the fabric to create a seamless finish where ankle boots wouldn’t. With miniskirts, they look inherently cool and work to balance out the short hemline.
Truly, dresses and knee-high boots make a perfect pairing, and I’m not the only one who thinks so. I keep daily tabs on what’s being searched for on Google, and whilst there are a surprising amount of queries around air fryers and iPads, amongst the tech and kitchen gadgetry, I can see the term “dresses with knee boots” is up by 100% since last week. Assuming, then, that you’re on the hunt for some dresses-with-knee-high-boots outfits to wear right now, I’ve assembled seven looks below that perfectly demonstrate how handy this pairing is. From minis to midis and heels to flats, scroll on to see the chicest ways to style the combination this winter.
9 Dresses and Knee-High Boots Outfits to Try:
1. Knitted Roll-Neck + Square Toe-Boots
Style Notes: When those cold-weather days arrive, you’ll be grateful for a chunky knit dress to keep you warm. Opt for a neutral shade to look put-together and add some chic square-toe boots.
Shop the Look:
MANGO
Perkins-Neck Ribbed Dress
I love this ribbed style.
Charles & Keith
Square-Toe Side-Zip Knee-High Boots
Some of my most comfortable shoes are from Charles & Keith.
2. Mini Jumper Dress + Riding Boots
Style Notes: Tap into the returning jumper dress trend by way of a few key buys. A mini knit dress in a fun colour will instill effortless energy and a knee-high boot and long sock pairing will add a relaxed edge whilst working to polish the look.
Shop the Look:
A pop of colour instantly brings joy to a dreary day.
STUART WEITZMAN
Celia Riding Leather Knee Boots
Drawing on equestrian inspiration, these boots are an easy way to add some interest into your day-to-day wardrobe.
3. Silk Dress + Stiletto Boots
Style Notes: Giving her heeled boots an even more elegant spin, influencer and stylist Sylvie Mus styled them here with a refined silk dress for an evening out in Paris. Retaining a sophisticated silhouette, the boots pairing added warmth and height to her evening outfit without distracting from the dress.
Shop the Look:
Reformation
Serafina Silk Dress
The lace trimmed detailing is so on trend right now.
Jimmy Choo
Agathe Knee Boot 85
Boots are such a worthy investment piece and an item you’ll love for years.
4. Draped Dress + Kitten Heel Boots
Style Notes: Draped dresses always look sophisticated and this is especially true when you pair them with kitten-heel boots. Wear on its own or opt for a chunky belt if you really want to dress it up.
Shop the Look:
Entire Studios
Draped Wool Maxi Dress
The perfect evening style.
H&M
Pointed Knee-High Leather Boots
I can’t believe these boots are from the high-street.
5. Knit Dress + Brown Boots
Style Notes: When the sunshine isn’t playing ball, reach for a cosy kitted dress and trending brown boots to see you through. Insulating you from those unexpected biting breezes, this comfortable combination will nod towards a major colour trend whilst keeping you snug in the process.
Shop the Look:
ALLUDE
Wool and Cashmere-Blend Turtleneck Maxi Dress
Chocolate brown is a softer alternative to black.
& Other Stories
Kitten Heel Leather Knee Boots
A brown boot is so sleek.
6. Minidress + Knee-High Boots
Style Notes: Channel the spirit of summer and pull out your favourite flirty mini a little early this season. To close the temperature gap whilst it’s still winter, style with warm tights and knee-high boots—and don’t be afraid to keep a maxi wool coat close to hand.
Shop the Look:
Dôen is such a good brand for dresses.
ZARA
Fitted High-Heel Boots
Black, pointed-toe boots are one of the most versatile pairs to have in your arsenal.
7. Pinafore Dress + Cowboy Boots
Style Notes: A pinafore dress is a summer staple, but with a heavy layer thrown into the mix, you can get your wear out of it during wintertime too. Style with chunky cowboy boots to toughen up the “feminine dress” and add some tights if there’s a breeze in the air.
Shop the Look:
Nobodys Child
Black Cord Chiara Pinafore Mini Dress
Wear over a white tee, chunky roll-neck or crisp cotton button-down.
Free People
Finn Tall Western Boots
Embroidered cowboy boots top so many wish lists.
8. Denim Dress + Flat Knee-High Boots
Style Notes: A denim dress doesn’t have to be reserved for summer; transition it into the winter seasons by layering it over a light knit and pairing with a flat knee-high boot for a chic, everyday outfit.
A darker denim is ideal for the colder seasons.
COS
Clean Cut Regular Long-Sleeved T-Shirt
The perfect basic white tee.
Ideal for those that don’t like wearing heels.
9. Bright Knitted Dress + Biker Knee-High Boots
Style Notes: Biker boots are such a big trend this season. The juxtaposition of pairing them with a bright knitted dress creates an instantly chic, interesting look.
Tommy Hilfiger
Cable Knit Midi Soft Wool Jumper Dress
ASOS
Off The Hook Adderstone Block Heel Knee High Leather Boots
A great high-street option.
