Not All Skirt-and-Boot Pairings Work, But These 5 Definitely Do

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.

Style Notes: How to update that pleated midi skirt you 100% have lurking in your closet? Simply add a slick pair of Western boots.

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.

Style Notes: Make like Danielle and pair a refined all-white outfit with chunky boots.

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.

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.

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.

Style Notes: Counterbalance the mini skirt with a chunky boot. The Row are renown for its boots, of course!

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.

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.

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