If there’s one styling tip I took away from street style spotting this September’s London Fashion Week, it’s this: in the eyes of the London crowd, there’s only one way to wear a midi skirt—and that’s with loafers and calf-grazing socks.
It’s true, knee-high boots can take a back seat for now. This season, the formal footwear is dominating London’s streets right now, and it looks like its influence is making waves across the pond as well.
Tapping into the trend in New York this week, Katie Holmes was spotted pairing a flowing, calf-skimming skirt with tall black socks and tortoise-print leather loafers. Creating an easy, chic silhouette with a distinct London edge.
(Image credit: Getty Images)
Loafers naturally carry a polished, collegiate appeal that lends any outfit a smart, considered finish. At the same time, their flat silhouette and subtle nod to menswear give them a grounding toughness—the kind of balance Londoners love to strike.
While Holmes opted for a soft brown knit on top, the city’s style set has been taking the same formula in a more casual direction, teaming midi skirts, loafers and socks with crisp white tees and oversized jackets as the first chills of autumn set in.
The detail that really makes the look feel “London”? The socks. Pulled high above the ankle, they add a preppy twist while offering the practicality of extra warmth—a clever styling choice that’s both functional and outfit-enhancing.
With Holmes and London’s most stylish women on board, it’s clear the midi-skirt-and-loafers combo is autumn’s chicest uniform. Scroll on to shop the best loafers and midi skirts to re-create the look for yourself.
Shop Midi Skirts and Loafers:
H&M
Pleated Twill Skirt
Between the trending tone and the chic box pleats, I can’t see this midi skirt staying in stock for long.
H&M
Loafers
Style with white socks to give your look a preppy feel.
COS
Draped Checked Midi Skirt
This skirt was a fashion person’s favourite during New York Fashion Week
Arrange
Leather Loafer in Black
These soft leather loafers are comfortable enough to style without socks.
Reformation
Carolina Silk Skirt
This also comes in six other shades.
Marks & Spencer
Leather Loafers
These also come in half sizes, so you can find your perfect fit.
COS
Rounded Cotton Midi Skirt
Mark my words: rounded skirts are going to be a major trend this season.
Mango
Gathered Leather Moccasin
The burgundy finish gives these a thoroughly modern look.
H&M
Midi Skirt
This comes in UK sizes 4—22.
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