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The New, Reimagined Prep

How to beat winter with bold color

Men's reimagined prep outfit inspiration

What’s better than vintage? Fresh pieces, like these J.Crew chinos ($138) that retain the era’s vibe but have been tweaked for today.

By

Valet. Staff
@valetmag

Published

February 19, 2026

Published

February 19, 2026

Photography

Courtesy

Note

Items featured in this story are independently selected by the editorial team. Purchasing via our links may earn Valet. a portion of the sale, which helps fund our editorial mission.

Winter has a way of draining the color out of everything—gray skies, dark coats, the same rotation of muted layers. But getting dressed doesn’t have to feel so bleak. This season, the easiest way to shake off the slump is to lean into bold, punchy hues and a little bit of old-school prep energy. Think bright knits, standout stripes, and pieces that feel equal parts playful and polished.

Right now, brands are fully embracing the throwback prep comeback, which means it’s never been simpler to work these relaxed staples into your everyday lineup. A colorful rugby shirt here, a classic loafer there, and suddenly your winter uniform feels a lot more fun. Or, you can take the full approach and pull it all together like we did here.

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Your Bold Prep Look

Men's reimagined prep winter outfit inspiration

Italian alpaca sweater, $150 / $119.99 by Banana Republic

Full-grain leather belt, $148 by Polo Ralph Lauren

Hadley sunglasses, $250 by American Optical

Corduroy cap, $58 by Rowing Blazers

Chuck Taylor All-Star 70 sneaker, $95 by Converse

Retro stripe sock, $15 by American Trench

Relaxed-fit double-pleated chino, $138 by J.Crew

U.S.-made canvas tote, $195 by J. Press

Clockwise, from top left

Italian alpaca sweater, $150 / $119.99 by Banana Republic

Full-grain leather belt, $148 by Polo Ralph Lauren

Hadley sunglasses, $250 by American Optical

Corduroy cap, $58 by Rowing Blazers

Chuck Taylor All-Star 70 sneaker, $95 by Converse

Retro stripe sock, $15 by American Trench

Relaxed-fit double-pleated chino, $138 by J.Crew

U.S.-made canvas tote, $195 by J. Press

FYI

J. Press men's spring 2025 New York fashion week

For its recent New York Fashion Week runway debut, J. Press paid homage to Take Ivy, the legendary 1965 anthology of Ivy League style photographed by Teruyoshi Hayashida.

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