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
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
Round-neck Cashmere-blend T-shirt
High-waisted Tapered Trousers
Edgy Coolness Combat Boot Tall
Stanley Puffer Jacket
Cleo Shoulder Bag
Turtleneck Sweater + Wool Skirt + Slouchy Boots
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
Danni V-neck Knitted Cardigan
Houndstooth-print Wool Straight Skirt
Stivale Slouchy Boots
Jackie 1961 Shoulder Bag
Transparent-frame Sunglasses
Layered Sweater + Blazer + Cropped Trousers
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.
Cropped Straight-leg Trousers
Cable-knit Cashmere Jumper
Single-breasted Pinstripe Blazer
Colorblock Leather Penny Loafers
Triomphe Shoulder Bag
Los Angeles Dodgers Baseball Hat
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