Preppy Menswear

Back to school: How to master preppy menswear

28 Feb 2024 | |By Hitanshi Kamdar

The essential guide to nailing this season’s hottest menswear trend

All products are chosen independently by our editors. Luxury London may earn commission on items purchased.

If you’ve got your ear to the internet, you might have heard whispers that streetwear is passé. The hoodies and bomber jackets that dominated the cool ‘fit pics are slowly being relegated back to loungewear status as preppy menswear comes into focus. The sweatshirts-worn-with-sport-jackets aesthetic sported across elite campuses across the globe is being co-opted into mainstream consciousness, and it’s time you got on board.

Propelled to popularity by Emerald Fennell’s Saltburn, preppy menswear is the ultimate expression of the old money aesthetic also exemplified by last year’s quiet luxury trend The preppy aesthetic has influenced many designers of late with brands such as Miu Miu, Gucci, Wales Bonner, and S.S. Daley all introducing elements of the private school aesthetic into their offerings. 

While preppy menswear outfits include certain quintessential building blocks, it’s the styling that makes the difference between an ironic smart casual outfit and a plain mess. Happily, we’ve employed our high fashion nous to put together a guide to acing preppy menswear for 2024.

Polo shirts

A basic and an essential, preppy menswear leans heavily on the polo shirt. The classic collared shirts are ideal summer wear and, for a nonchalant British school boy aesthetic, should be worn oversized with a casual ease. While originally designed for the quintessential prep-school sport – polo – they’re also great for numerous other sporting attires, including golf and tennis.

We recommend investing in a timeless option, such as the cotton-piqué staples from Tom Ford, Loro Piana, or Brunello Cucinelli. Pair with chinos and penny loafers or lean into casual styling with Mr P.’s open-knit polo shirt which pairs well with straight-leg jeans.

Tom Ford cotton piqué polo shirt

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Loro Piana cotton piqué polo shirt

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Brunello Cucinelli slim-fit cotton piqué polo shirt

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Mr P. open-knit ribbed cotton polo shirt

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Rugby shirts

Close relative of the polo shirt, the rugby shirt toes the line between rugged and refined. Crafted to survive savage scrums in muddy fields, these collared shirts are typically made from heavier fabrics and feature horizontal stripes or brightly coloured panels.

Ralph Lauren is always a safe bet for preppy style, and its green and blue striped rugby shirt detailed with the signature Polo Pony logo is a great staple. Alternatively, try Nike’s subtle blue and white option for a low-key look or Drake’s design for a more streamlined and refined approach. Beams Plus offers a retro take on the trend with a navy, dark green, and mustard jersey complete with ribbed hems and cuffs.

Polo Ralph Lauren striped logo-embroidered rugby shirt

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Beams Plus striped cotton-jersey rugby shirt

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Nike Life twill-trimmed striped rugby shirt

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Drake’s cotton rugby shirt

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Oxford shirts

Even though Oxford shirts take their name from the weave of the cloth they’re crafted from – not the university – they are perfectly at home on the storied campus. The classic Oxford shirt as we know it today is said to have been created by American menswear outfitter Brooks Brothers. With a button-down collar and tailored fit, Oxford shirts layered under jumpers are as preppy as it comes.

Sunspel’s soft white cotton Oxford shirt is a great multitasking piece while Polo Ralph Lauren and Pink’s expertly woven shirts make for great office wear. Elsewhere, Thom Browne puts a more casual spin on the look with a sporty pink shirt featuring a contrasting placket and collar. Its buttons are concealed on the lower half, lending it a rugby shirt-style appearance.

Sunspel cotton Oxford shirt

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Polo Ralph Lauren cotton Oxford shirt

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Thomas Pink classic fit Oxford shirt

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Thom Browne grosgrain-trimmed supima cotton Oxford shirt

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Layering goes a long way when it comes to preppy menswear: cable-knit jumpers and sweater vests provide a grown-up alternative to collegiate sweatshirts and hoodies. While crew neck and turtleneck jumpers are classic, for a preppy look, mix it up with V-neck jumpers and button-up cardigans.

The Elder Statesmen and Alex Mill present luxurious cable-knit jumpers primed for layering over Oxford shirts while Polo Ralph Lauren’s blue jumper will pair wonderfully with a T-shirt. Prada’s cashmere cardigan paired with a T-shirt, black jeans and a bomber jacket exudes casual elegance. Alternatively, add preppy professor vibes to your look with a sweater vest such as Agnona’s beige knit or Maison Kitsuné’s whimsical fox-patterned Argyle knit.

Polo Ralph Lauren Polo Pony-embroidered wool jumper

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The Elder Statesman cable-knit cashmere and cotton-blend jumper

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Alex Mill cable-knit merino wool-blend jumper

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Prada cashmere cardigan

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Agnona ribbed cotton and cashmere-blend sweater vest

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Maison Kitsuné profile fox argyle knitted sweater vest

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Since preppy style channels a dichotomy of sportswear and professorial attire, blazers are key to perfecting your outfit. Traditionally, tweed blazers with elbow patches or blazers emblazoned with school emblems were worn but, for 2024, the elbow patches are taking a back seat and oversized silhouettes are gaining popularity.

Bottega Veneta’s single-breasted jacket is crafted from brown tweed, adding a tactile edge to your outfit, while The Frankie Shop plays with shoulder pads for a boxy oversized jacket. For a touch of royalty, opt for Paul Smith’s Prince of Wales check blazer or, for something more unique, consider Clothsurgeon’s collarless blazer which is an amalgamation of streetwear and Savile Row tailoring.

Bottega Veneta single-breasted suit jacket

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Paul Smith Prince of Wales checked wool, cotton and linen-blend blazer

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The Frankie Shop Beo oversized woven suit jacket

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Clothsurgeon grey flannel collarless blazer

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Wide-leg jeans

While we’re glad skinny jeans are showing no sign of return, to embrace a preppy vibe, replace your straight-leg jeans for ones with a wider hem. From Gucci and Balenciaga to Agolde, brands across the spectrum offer great relaxed fit options. To really lean into the aesthetic, pick a pair with a slightly faded, worn-in vibe. But be warned, if they’re ripped, you’ve gone too far into grunge style.

Agolde Otto Carpenter wide-leg organic jeans

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Vetements wide-leg jeans

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Balenciaga wide-leg jeans

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Modern day chinos were derived from the lightweight cotton twill trousers worn by British soldiers in the mid-19th century. The straight-leg mid-rise trousers are incredibly comfortable and versatile, pairing well with everything from formal shirts to casual sweatshirts. While preppy menswear traditionally features bright red or pink chinos, for 2024, stick to minimalist options in beige, navy, ecru, and blue from brands such as Tom Ford and JW Anderson among others.

Tom Ford straight-leg cotton chinos

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Polo Ralph Lauren slim-fit embroidered cotton-blend twill chinos

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Drake’s straight-leg cotton-twill chinos

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JW Anderson straight-leg chino trousers

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