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The New Rules of Men's Preppy Style
Content editor
Jayne Cherrington-Cook
What is preppy style?
Born in the hallowed halls of America's Ivy League universities, preppy style for men is the ultimate mix of sporty comfort and timeless classics. It's all about clean lines, effortless elegance and a touch of sophistication. This iconic look is back, proving that classic style never goes out of fashion.
While its DNA has remained largely unchanged since the 1950s — high-quality fabrics and core pieces like Oxford shirts, blazers and chinos — today's interpretation brings fresh energy to the classic dress code.
Rather than adhering to rigid rules, modern preppy outfits for men involve mixing heritage elements with contemporary pieces.
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How to build a preppy wardrobe
Looking to master the art of modern preppy clothes for men? The key lies in giving those timeless classics a contemporary twist. No need to go full Carlton Banks – think of it as adding a hint of prep to your style.
Start with the essentials: crisp Oxford shirts in white and light blue and perfectly fitted khaki or beige chinos. Add a crew-neck sweater in merino wool or cashmere and a navy blazer (brass buttons optional) for an extra touch of polish. Incorporate classic patterns like stripes and nautical motifs but always keep quality and fit in mind; these are investment pieces that should last for years.
Loafers are a preppy footwear staple that work just as well with shorts as they do with trousers. And when the sun comes out, you can't beat a classic pair of boat shoes.
Complete your collection with timeless accessories: a leather belt, some striped ties, a baseball cap and a messenger bag.
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Preppy style: The 2025 edit
Start small by introducing one or two preppy pieces into your existing wardrobe. A shirt under your favourite jumper, a check scarf worn over a coat or a blazer over a white t-shirt can reference prep style without feeling forced.
Once you've got the basics down, don't be afraid to experiment and have some fun. Mix a traditional cricket sweater with selvedge denim, or pair boat shoes with straight leg joggers.
The great thing about preppy outfits is that they can take you anywhere. For casual weekends, channel the relaxed prep of the '80s with a sweatshirt, chinos and white trainers. Heading to the office? Sharper lines are key: a navy blazer over a crisp shirt, paired with loafers. Want to dial up the '90s nostalgia? Throw a jumper over your shoulders, add a polo shirt and pull on some loose fit jeans.
Get prepped with the basics
Published 1.26.2025
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