For every coffee run, meeting, and brisk city stroll, this effortless yet undeniably elevated look gets the job done
In the vocabulary of modern wardrobing, certain pairings act as reliable shorthand for “cool.” There is the oversized blazer draped over a silk slip, denim paired with a perfect white tee, and, most recently, the high-octane collision of the sweeping maxi skirt and the humble lifestyle sneaker. While the fashion world has long flirted with the “ugly-chic” movement, the industry’s most discerning eyes have now settled on this specific silhouette, a look that prioritises both the stride and the soul.
There is something fundamentally “cool-girl” about taking a garment associated with evening grandeur or bohemian whimsy and pairing it with the rubber-soled grit of an athletic shoe. It is a look that says you have places to be, but you’re in no rush to appease traditional dress codes.
The new proportions
The key to getting this pairing right in the depths of winter lies in balance, specifically, weight and counterweight. We are moving away from the “dad shoe” bulk of yesteryear toward a more streamlined, aerodynamic foot. Think of the PUMA Speedcat or the Onitsuka Tiger Mexico 66, sneakers with a slim profile that don’t compete with the floor-grazing hem of a heavy wool or denim maxi.
When your skirt forms a clean column, whether through colour, texture, or cut, a low-profile sneaker allows the eye to move freely, uninterrupted, preserving that elongated line. Even in January’s slush-heavy reality, a well-worn Adidas Samba does most of the heavy lifting, grounding the look while keeping it sharp, practical, and convincingly modern.
The ultimate styling guide to sneakers and maxi skirts for cold weather
The corpcore
The office wardrobe has finally loosened its grip. Replace the stiff trousers with a structured, charcoal wool maxi skirt from designers like The Row or Tom Ford. The key here is the “sandwich method”: match your footwear to your knitwear or go the other way and lean into playful colour blocking. A dark, earthy turtleneck with New Balance Numeric 933 Reynolds trainers creates a frame for the skirt, turning a functional commute outfit into a deliberate sartorial statement. It’s the ultimate “desk-to-dinner” pivot for the woman who refuses to carry a change of shoes in her tote.
Boho warmth
Channel winter’s earthy tones by pairing Salomon XT-6 sneakers in olive with a tiered, printed maxi skirt from Dries Van Noten. The key to making this work in freezing temperatures? Layer a chunky knit cardigan over a fitted long-sleeve tee, and add a quilted puffer vest for warmth that doesn’t overwhelm the silhouette. Wool tights in a complementary tone keep legs warm while the technical sneakers handle icy pavements. Finish with a crossbody bag, and you’re ready for winter market browsing or weekend brunches.
Minimalist monochrome
Embrace winter’s moodier palette with an all-neutral approach. Choose a flowing jersey or ribbed knit maxi in black, charcoal, or chocolate brown, and pair it with tonal sneakers in suede or nubuck. Toteme’s Sport sneakers or Veja’s V-10s capture this aesthetic perfectly. Layer a long cashmere cardigan or oversized blazer in a matching shade, keeping everything within the same colour family for a streamlined, elongating effect. Add textures through accessories: a leather crossbody bag, wool scarf, and perhaps a structured wool beanie. This monochromatic approach feels sophisticated and intentional, proving that comfort dressing can be utterly chic.
The winter floral
Who says long skirts are reserved for summer meadows? A dark-ground floral maxi, styled with a black oversized blazer, becomes a winter staple when paired with a crisp, white Nike Cortez or a vintage-inspired Autry medalist. This look leans into the “eclectic grandpa” trend that has dominated 2025, offering a playful nod to spring while staying firmly rooted in the current temperature.
