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6 Ways To Wear Loafers With Socks And Midi Skirts In Autumn/Winter 2025

Fashion recently has been defined by shoes. They’re the way to make a bold statement: from the popularity of furry styles sweeping through every brand from Dries Van Noten to Erdem, to Margiela Tabis taking over the mainstream. At the moment, however, we’ve decided to go back to basics, following the classic fashion lessons of Miu Miu and Givenchy.

The best loafers stood out on the runway not only for their timelessness, but also for their versatility. Ranging from chunky soles to flat, they often come in neutral colours like brown and black, but also often dabble in red, oxblood and burgundy.

Street style experts, always on the lookout for autumn/winter 2025 shoe trends, have wasted no time in establishing loafers as a piece that can be just as interesting as furry footwear. Worn with socks and midi skirts, they give off that preppy chic energy that works just as well for the office as it does for a day out.

Here are our tips for wearing loafers with socks and midi skirts this autumn/winter 2025

Opt for comfortable garments such as sweaters

Katie Holmes con mocasines calcetas falda midi y suter en Nueva York.

Katie Holmes con mocasines, calcetas, falda midi y suéter.Michael Simon / Getty Images.

In recent years, Katie Holmes has become a great reference for dressing comfortably with pieces that don’t shout, but command attention nevertheless. One of her tricks is to wear socks with patent loafers, giving that academic look but with a fun twist. The result is a casually distinguished aesthetic, with a camel sweater and black midi skirt.

ASOS DESIGN Milan Chunky Chain Detail Loafers

Ella Wool-Cashmere Crew-Neck Jumper

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A solid, neutral colour palette never goes wrong

Mocasines con calcetas falda midi y blusa sin mangas en el street style.

Mocasines con calcetas, falda midi y blusa sin mangas.Valentina Valdinoci / Launchmetrics / Spotlight.

LP Staff Writers

Writers at Lord’s Press come from a range of professional backgrounds, including history, diplomacy, heraldry, and public administration. Many publish anonymously or under initials—a practice that reflects the publication’s long-standing emphasis on discretion and editorial objectivity. While they bring expertise in European nobility, protocol, and archival research, their role is not to opine, but to document. Their focus remains on accuracy, historical integrity, and the preservation of events and individuals whose significance might otherwise go unrecorded.

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