At this time of year, skirts are a hard-and-fast staple. Whether you lean towards the knitted, silky or mini variety, there's no doubt that this chic choice of bottoms is endlessly versatile and transitional-weather appropriate.
Ankle boots sit right up there with skirts on the top tier of autumn essentials. So it makes sense that we would style these two hero items together. Certain outfit formulas work every time, but landing on the right combinations is often a process of trial and error. Luckily, we've consulted the It girls of Instagram to teach us a few lessons in pairing ankle boots with skirts so you can skip ahead to the good part: wearing your winning look.
Scroll on to find out which shape to team with that liquid-looking midi you've been reaching for or the silhouette that works best with a mini. These five effortless outfits sure show us how it's done.
1. Pleated Midi + Cowboy Boots
Style Notes: How to update that pleated midi skirt you 100% have lurking in your closet? Simply add a slick pair of Western boots.
SHOP THE LOOK:
This particular knit design looks very expensive.
A simple piece you'll keep coming back to.
Also very cool with jeans, leggings, dresses… the lot.
A classic black handbag goes with almost everything you already own.
2. Lug-Soled Boots + Monochrome Co-ord
Style Notes: Make like Danielle and pair a refined all-white outfit with chunky boots.
SHOP THE LOOK:
You can also pop this knit on with jeans.
You'll get so much wear out of this midi.
M&S is really killing it this season.
3. Western Boots + Midi Skirt
Style Notes: Cowboy boots and silky fabrics are a match made in fashion heaven. There's something about the rawness of a Western style that contrasts dreamily with a fluid, feminine skirt.
SHOP THE LOOK:
Wear this fluffy knit with a floral dress for a distinctly boho look.
The final flourish to elevate your outfit.
I bet this satin skirt moves beautifully.
Come Autumn, cowboy boots come back around like clockwork. I love this elegant pair.
4. Striped Jumper + Leather Mini Skirt + Zip-Front Boots
Style Notes: Counterbalance the mini skirt with a chunky boot. The Row are renown for its boots, of course!
SHOP THE LOOK:
It's almost time to bring out the knits!
Size up for a slouchy look like Francesca's!
You'll never regret investing in a mini leather skirt.
The Avocado hued Loewe is stunning.
Seasons after its release this still continues to be a coveted boot style.
5. Shearling Gilet + Black Denim Skirt + Chelsea Boots
Style Notes: Girls about town, take note. While this outfit is polished, you won't feel restricted as you work your way through your to-do list. Sounds like the best of both worlds to me.
SHOP THE LOOK:
From summer to autumn, an embroidered blouse is the fashion gift that keeps on giving.
This denim skirt will be with you for life.
The perfect transitional piece.
This bag looks like high-end designer.
No autumn/winter wardrobe is complete without a chunky Chelsea boot.
Next Up, I'm a Stylist - My Wardrobe Wouldn't Function Without This Simple Piece
-
These 2 Effortless Pieces Are the Key to One of the Most Classic Outfit Combos EverI bet they're in your closet right now.
-
Sienna Miller Just Wore the Boot Trend Fashion People Use to Make Jeans Outfits Look ChicerI'll be copying this look all season.
-
32 Timeless Knee-High Boots to Elevate Your Fall WardrobeThe star of the show.
-
Taylor Swift Just Wore Another Polarizing Boot Trend to a Chiefs GameYou'll love it or hate it.
-
This Boot Trend Is Considered Intimidating by Some, But Sienna Miller Just Proved How Chic It Actually IsSo nice she wore them twice.
-
Move Over, Black Boots—33 Animal-Print Pairs Worth Purchasing for FallWalk on the wild side.
-
Bella Hadid Touched Down in Paris and Immediately Put on This 2025 Boot TrendSee how she styled the edgy shoes with leggings.
-
From Cool Flats to Elegant Kitten Heels, These Are the 36 Best Boots on the InternetFrom Mango, Reformation, Khaite, and more.
