Street style experts show the versatility of a midi skirt with socks and loafers
Street style experts, always on the lookout for Winter 2025 trends, have wasted no time in establishing that loafers, even as controversial as furry ones can be interesting, if worn with socks and midi skirts. So, here is Vogue’s edit for wearing loafers with socks and midi skirts this Winter 2025.
Lean into cosy staples
In recent years, Katie Holmes has become a key reference for dressing comfortably with pieces that subtly redirect the look. One of her tricks is wearing socks with loafers. With patent loafers, she leans into a casually polished aesthetic, pairing them with a camel sweater and a black midi skirt.
Neutrals always deliver
Neutral colours have long been essential for minimalists, and they remain the perfect formula for looking put-together with minimal effort. While an all-black outfit will never go out of style, in the second half of the year, brown pieces—like striped midi skirts and sleeveless blouses—become foolproof options, especially when worn together. Simply add black almond-toe loafers, long white socks and a blazer for a structured, versatile look.
Try statement shapes
T-shirts aren’t just wardrobe basics; they’re surprisingly useful when paired with more dramatic items like midi balloon skirts. Jane Birkin used this trick in the 60s with flared pants, and today Kaia Gerber and Nicole Kidman apply it to dress pants and heels. It keeps the silhouette from feeling overloaded and lets you play with cropped, short-sleeved jackets and black loafers with socks.
Make the combo your own
This pairing naturally evokes the preppy aesthetic that Gen Z has embraced—Miu Miu being a major reference. But that doesn’t mean more mature wardrobes can’t explore it, whether through beige pleated midi skirts, polo shirts or classic black button-downs.
Let details do the work
Turtleneck sweaters are signature pieces for the season. Besides offering warmth, they can add a touch of drama through sequins, puffed sleeves or structured shoulders. These details instantly elevate an outfit, whether worn casually with jeans or for something more refined with straight midi skirts, flat loafers and black socks.
Mix moods for impact
Mixing contrasting aesthetics has been a key concept in recent seasons. Hybrid shoes—like sneakerinas—and unexpected juxtapositions are everywhere in major fashion capitals. An easy way to tap into this idea is by mixing romantic and urban elements: think sheer lace midi skirts with loafers and socks, topped with an oversized denim shirt.
