Shoes
Aug 21, 2023

Not All Shoes and Skirts Go Together, But These 7 Autumnal Pairings Are Perfect

by Bébhinn Campbell

I wish I could tell you that all skirt-and-shoe pairings are classic and never-changing, but that would be misleading. Truthfully, we're talking about two items that feature heavily in the trends, and while some shapes and silhouettes will always be relevant, others are admittedly short-lived. Certain dressers might steer clear of these and invest solely in seasonless buys—think a black slip skirt and Chelsea boots. But if you do care about what’s current (because let’s face it, trying out trends can be so much fun), there are a few combinations worth considering for 2023.

That being said, when curating our favourite formulas we've focused on pieces we see sticking around for longer than a season. Even if they fade from the spotlight temporarily, these featured styles are worth holding onto. Trends aren't just fun; they're also circular.

Maybe you keep spotting denim skirt looks floating around Instagram and you're keen to give it a go, or perhaps you're wondering which kicks go best with a '90s mini. Either way, you're in the right place. Keep scrolling for the skirt-and-shoe outfit inspiration you've been searching for.

Shoes to wear with skirts: @aude_julie styles a denim midi skirt with loafers

Photo:

@aude_julie

Style Notes: It seems denim midi skirts are the it-buy of the season. Together with some slide-on loafers and a simple tank top, you have yourself a cool end-of-summer look.

SHOP THE LOOK:

Arket Ribbed Racer Tank

Ribbed Racer Tank

This taupe shade is a nice change from white and black.

Reformation Jayde High Rise Denim Midi Skirt

Jayde High Rise Denim Midi Skirt

Reformation's denim is well worth the price.

Prada Weejuns 90s Penny Slides Black Leather

Weejuns 90s Penny Slides Black Leather

I expect to see these everywhere over the coming months.

Shoes to wear with skirts: @annelauremais styles a leather mini skirt with knee-high boots

Photo:

@annelauremais

Style Notes: Mini skirts and and knee-high boots are a match made in heaven. It's a distinctly retro look, especially when you layer a suede trench coat on top, like Adenorah.

COS Leather Mini Wrap Skirt

Leather Mini Wrap Skirt

Wear with a t-shirt now, and pair with a jumper and tights come autumn.

Shoes to wear with skirts: @francescasaffari styles a slip skirt with trainers

Photo:

@francescasaffari

Style Notes: For an easy-going everyday combo, team a silky midi or maxi skirt with complementary trainers and a tank top. Keep a slouchy knit on hand in case the chill hits.

SHOP THE LOOK:

Arket Bouclé Jumper

There's never a wrong time to invest in good knitwear and a cream sweater like this will serve you well for cooler summer evenings.

Veja Venturi Panelled Suede Trainers

Venturi Panelled Suede Trainers

Veja sneakers are famously popular among in-the-know fashion people.

Shoes to wear with skirts: @frannfyne styles a midi skirt with ballet flats

Photo:

@frannfyne

Style Notes: Swap out your chunky sandals for dainty ballet flats as we enter chillier days—I already own a black pair, so I'll be seeking a burgundy iteration similar to Franny's.

SHOP THE LOOK:

Whistles Navy Crepe Boyfriend Blazer

Navy Crepe Boyfriend Blazer

Don't overlook the timeless nature of navy.

Chloé Striped Wool and Cashmere-Blend Midi Skirt

Striped Wool and Cashmere-Blend Midi Skirt

This skirt is an investment, yes, but if you're looking for a great quality piece that will last you for years, this is it.

Ballerette Burgundy Leather Ballet Flats

Burgundy Leather Ballet Flats

The bow detailing makes this pair feel really traditional.

Shoes to wear with skirts: @bubblyaquarius wears a cotton maxi skirt with clogs

Photo:

@bubblyaquarius

Style Notes: Make the most of the last few weeks of summer and combine light neutrals in the form of a beige waistcoat, white maxi skirt and classic Birkenstocks.

SHOP THE LOOK:

COS The Longline Waistcoat

The Longline Waistcoat

A great layering piece for the autumn months.

Reformation Carine Linen Skirt

Carine Linen Skirt

This is on sale, so grab it before it sells out!

Birkenstock Boston Suede Clogs

Boston Suede Clogs

The Boston is a bestseller for good reason.

Shoes to wear with skirts: @shhtephs styles a plaid mini skirt with taupe court shoes

Photo:

@shhtephs

Style Notes: There's something so pretty about a mini skirt and block heel combination. I love that Stephanie has completed the look with a sheer shirt to tap into current trends.

SHOP THE LOOK:

Asos Design Sheer Lace Shirt With Tie Cuff Detail in White

Sheer Lace Shirt With Tie Cuff Detail in White

This is *perfect* for the season we're in.

Rowen Rose Checked Tweed Mini Skirt

Checked Tweed Mini Skirt

This has such a Parisian feel about it don't you think?

Shoes to wear with skirts: @sophiabrenn styles a cargo skirt with cowboy boots

Photo:

@sophiabrenn

Style Notes: If you're still not sure how to feel about the cargo pant revival, perhaps the skirt version is more to your taste. Sophia makes a strong case for styling it with cowboy boots in this Y2K-tinged outfit.

SHOP THE LOOK:

Weekday Turn Printed Long Sleeve

Turn Printed Long Sleeve

This is a lot of fun.

M&S Collection Pure Cotton Maxi Cargo Skirt

Pure Cotton Maxi Cargo Skirt

I never thought I'd want a cargo maxi skirt, but here we are.

Matisse Vegan Ranch Boot

Vegan Ranch Boot

A wearable take on the western boot.

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