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Why There's No Off-Season for This Timeless Manner of Dressing

Prep is the ultimate anti-trend style.

Style Equations
Why There's No Off-Season for This Timeless Manner of Dressing
Photos: Edward Berthelot/Getty Images (left and right); Valentina Frugiuele/Getty Images (right)

If there’s one thing I appreciate about preppy style, it’s the emphasis on timelessness. Prep is fundamentally anti-trend, its disciples opting for a spare wardrobe of durable, impeccably-made essentials. This functional subset of style especially shines in the cold weather; think long tartan skirts, button-up shirts worn under cashmere sweaters, and heavy wool coats. (Hint: this all revolves around layering.) Here, we’ve compiled three ways to wear prep staples this winter, all composed of quality garments designed to last.

Vest + Camel Trousers + Knee-high boots

Photo: Edward Berthelot/Getty Images

I have never been a horse girl, but the equestrian vibe of this ensemble just might convert me. With its durable, thick-soled boots and a long, down jacket, it’s the perfect outfit for trudging through the snow in style.

Ribbed Knit Top

Saint Laurent

Round-neck Cashmere-blend T-shirt

Stefano Mortani
$151 $128

High-waisted Tapered Trousers

Alberta Feretti
$539 $351

Edgy Coolness Combat Boot Tall

Dorothee Schumache
$750 $525

Stanley Puffer Jacket

Lenki Lenki
$1470 $1323

Turtleneck Sweater + Wool Skirt + Slouchy Boots

Photo: Edward Berthelot/Getty Images

A sweater draped around the shoulders of the sweater you are already wearing is the ultimate prep styling move. Oversized sunglasses and slouchy boots add a little flare to the classic turtleneck and wool skirt combination.

Turtleneck Ribbed Jumper

3.1 Phillip Lim

Stivale Slouchy Boots

Paris Texas
$730 $635

Layered Sweater + Blazer + Cropped Trousers

Photo: Valentina Frugiuele/Getty Images

If Succession has taught me anything, it’s that a good baseball hat pairs perfectly with luxury clothing. Cropped trousers can be a challenge to style, but you can’t go wrong with grey socks and loafers.

Cable-knit Cashmere Jumper

Polo Ralph Lauren
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