Skirts are back for the season—and the idea is to wear them with loafers, which are arguably the most comfortable, stylish footwear options since bursting onto the scene circa 1950s. As much as I have a soft spot for a look Vogue shopping writer Augustine Hammond once described as “sulky-rich-girl-in-detention”, I understand that others would rather not resemble an extra in St Trinian’s. Loafers, with their academic associations, can easily fall into this category, particularly when paired with a sensible skirt. But as this season’s street style demonstrates, a few styling tweaks can take the combination well beyond the room. Below, we take a look at how to style a skirt and loafers without conjuring up the distant sound of the school bell.
Tartan skirt and leather jacket
NEW YORK, NEW YORK - FEBRUARY 15: A guest wears long black hair, a black leather jacket, a yellow crew neck sweater, a gray plaid A-line pleated skirt, burgundy socks, burgundy leather loafers shoes, outside Diotima, during New York Fashion Week, on February 15, 2026 in New York City (Photo by Edward Berthelot/Getty Images)
Edward Berthelot/Getty ImagesSwap the blazer for a leather jacket, preferably an oversized bomber with a bit of wear and tear. Add an asymmetric skirt to give your loafers a less studious feel.
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Matching monochrome
Claudio Lavenia/Getty Images
For a more polished take, pair classic leather loafers with a monochrome outfit like this one – proof that a long, straight skirt and a simple jacket are all you need to elevate your slip-ons.
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Milano ribbed jacket, Uniqlo, ₹3,990
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Slip skirt and long sleeves
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Valentina Frugiuele/Getty Images
For a more relaxed look, pair your leather loafers with a simple slip skirt and a baggy long-sleeved T-shirt. Throw on a hobo bag that can lug your essentials for that truly carefree look.
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Pencil skirt and knitwear
Edward Berthelot/Getty Images
Tap into ladylike style by pairing your loafers with a long leather pencil skirt, your favourite knitwear and a do-it-all bag. Keep the colours tonal in rich autumn shades.
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Wool cardigan, Prada, price on request
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Arma Meeka paneled full-grain leather midi skirt, Net-a-Porter, ₹53,986
Patterns galore
Edward Berthelot/Getty Images
Add a bit of flair to a simple pair of loafers by embracing clashing patterns up top. Simply style classic brown or black shoes with a statement skirt and an equally eye-catching knit.
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This story originally appeared on Vogue.uk
Also read:
Channelling ’90s feminine style? Pair flowy skirts with ankle boots
3 ways to wear floral skirts this season
Midi skirts, socks and loafers are the chicest street style trio