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 2024.
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
Style Notes: It seems denim midi skirts are the it-buy of the season. Together with some slide-on loafers and a simple suede jacket, you have yourself a cosy look.
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This jacket's caramel shade, faux shearling lining and cropped silhouette make it a promising option for winters to come.
I love how sleek this frayed denim midi skirt is—it will work all year round.
I expect to see loafers everywhere as we move into spring.
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 trench coat on top, like Adenorah.
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An outerwear staple.
Pair with a jumper and tights in the colder months, and with a T-shirt come spring-summer.
A truly timeless shape.
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, before layering with a slouchy knit for when the chill hits.
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There's never a wrong time to invest in good knitwear and a cream sweater like this will serve you well.
This is so chic.
Colourful Adidas sneakers are so popular among in-the-know fashion people right now.
4. Midi Skirt + Ballet Flats
Style Notes: Dainty ballet flats are great alternative to heels when wanting to dress up a skirt. I already own a black pair, so I'll be seeking a burgundy iteration similar to Franny's.
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Don't overlook the timeless nature of navy.
This skirt is an investment, yes, but if you're looking for a great quality statement piece that will last you for years, this is it.
The burgundy hue makes this pair super on-trend.
5. Maxi Skirt + Clogs
Style Notes: The winter-to-spring transition is all about layers, so try combining neutrals in the form of a quilted vest, denim maxi skirt and classic Birkenstocks, just like Taffy.
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A great layering piece for unpredictable weather.
This one comes in short, regular and long, so you can achieve your perfect maxi length.
The Boston is a bestseller for good reason.
6. Plaid Skirt + Block Heels
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 and shearling-trimmed coat.
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A button-down shirt with a twist.
This has such a Parisian feel, don't you think?
These Mary Janes feel so classic.
7. Tailored Midi Skirt + Leather Boots
Style Notes: If you're still not sure how to feel about jumping on the current fashion trends, it never hurts to stick to timeless and minimalist looks. Ilirida has done just that in her chic tailored midi skirt, roll-neck jumper and leather boots.
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A belted wool coat is a must-have.
Simple but effective.
There's a reason Vagabond's boots are so loved.
This story was published at an earlier time and has since been updated.
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