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

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.

1. Denim Skirt + Loafers

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



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.


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

I expect to see these everywhere over the coming months.

2. Leather Mini + Knee-High Boots

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. 

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

3. Slip Skirt + Trainers

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.


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

4. Midi Skirt + Ballet Flats 

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



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.


Don't overlook the timeless nature of navy. 

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.

The bow detailing makes this pair feel really traditional.

5. Maxi Skirt + Clogs

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.


A great layering piece for the autumn months.

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

The Boston is a bestseller for good reason.

6. Plaid Skirt + Block Heels

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



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.


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

7. Cargo Skirt + Cowboy Boots

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



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.


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

A wearable take on the western boot.

This story was published at an earlier time and has since been updated.

Next Up, 8 Major Dress Trends That Will Be Everywhere This Autumn