Tommy Hilfiger Gives Prep a Roguish Turn for Spring

The Fashionisto / Published September 12, 2026
Tommy hilfiger spring

Tommy Hilfiger sets the stage for its spring 2027 collection at The Plaza, and immediately disrupts the historical ambience. The season engages the brand’s prep codes with a modern, roguish hand.

The strait-laced Tommy Hilfiger man has modern ambitions, and his wardrobe reflects that. The silhouette expands as loose, slouchy proportions meet polos, rugby shirts, blazers, chinos, and windbreakers.

Pants continue the season’s story as hems pool around sneakers and shorts dip below the knee, borrowing from skater proportions. Even tailoring is lax as brash layers oppose any sense of modesty.

Colors live large, with a vibrant yellow taking up residence among a clash of tartans, stripes, and Tommy Hilfiger’s signature tricolor. The styling pushes each piece to the brink of good taste, mirroring the tenacity of a young generation that treats fashion references like material for a high-impact collage.

Four decades into the brand, Tommy Hilfiger bets the future of prep not on a rigid set of rules, but on letting a new generation rewrite them.

Tommy Hilfiger Spring 2027 Collection

A model in a checked oversized blazer over a yellow graphic polo, with khaki shorts and red sneakers, for Tommy Hilfiger's spring 2027 collection
A model in a green baseball cap and beige blazer over a plaid shirt, with red shorts and white sneakers, for Tommy Hilfiger's spring 2027 collection
A model in a color-blocked rugby polo with a 'Tommy' wordmark, wide-leg trousers, and a canvas tote bag, for Tommy Hilfiger's spring 2027 collection
A model in a red rugby polo with a 'Tommy' wordmark and plaid shorts, styled with brown loafers, for Tommy Hilfiger's spring 2027 collection
A model in a bucket hat and colorblock sweater with a Tommy Hilfiger flag-logo tote bag and khaki trousers, for Tommy Hilfiger's spring 2027 collection
A model in a colorblock hooded jacket layered over a denim jacket and striped tie, with shorts and white sneakers, for Tommy Hilfiger's spring 2027 collection
A model in a plaid bucket hat and polo shirt with plaid shorts, styled with brown loafers, for Tommy Hilfiger's spring 2027 collection
A model in a bucket hat and beige trench coat with dark green wide-leg trousers and a knit tie, for Tommy Hilfiger's spring 2027 collection
A model in a green cap and plaid overshirt with a striped tie, dark green trousers, and a bucket bag, for Tommy Hilfiger's spring 2027 collection
A model in a striped zip jacket over a pink collared shirt, with light-colored shorts and a red belt, for Tommy Hilfiger's spring 2027 collection
A model in a plaid bucket hat and plaid shirt with a striped tie and khaki wide-leg trousers, for Tommy Hilfiger's spring 2027 collection
A model in a sheer pastel bomber jacket layered over necklaces, with shorts and red-and-white sneakers, for Tommy Hilfiger's spring 2027 collection
A model in a cap and red jacket over a striped wordmark sweater, with pinstripe shorts, for Tommy Hilfiger's spring 2027 collection
A model in an oversized striped shirt over a red collar, with a striped-strap tote bag and light-colored shorts, for Tommy Hilfiger's spring 2027 collection
A model in a plaid blazer over a colorblock wordmark polo, carrying a flag-print tote bag with khaki trousers, for Tommy Hilfiger's spring 2027 collection
A model in a colorblock hooded anorak with a plaid body over a yellow polo, paired with dark green shorts, for Tommy Hilfiger's spring 2027 collection
A model in a plaid half-zip jacket over a green-collar polo, with dark denim jeans and a tote bag, for Tommy Hilfiger's spring 2027 collection
A model in a ribbed sweater with a collegiate 'Hilfiger' graphic over a pink polo, paired with shorts, for Tommy Hilfiger's spring 2027 collection
A model in a mustard cable-knit polo over a green collar, with light wide-leg trousers, for Tommy Hilfiger's spring 2027 collection
A model in a gray zip jacket over a striped polo, with shorts and white sneakers, for Tommy Hilfiger's spring 2027 collection
A model in an overshirt worn open over a green polo, with yellow wide-leg trousers and a flag-print tote bag, for Tommy Hilfiger's spring 2027 collection
A model in a green cap and gray parka over a plaid shirt with a striped tie, paired with dark denim jeans, for Tommy Hilfiger's spring 2027 collection
A model in a colorblock hooded anorak over a plaid collar shirt, with khaki shorts and loafers, for Tommy Hilfiger's spring 2027 collection
A model in a tan checked blazer over a striped polo, with green wide-leg trousers, for Tommy Hilfiger's spring 2027 collection
A model in a tartan plaid jacket over a checked shirt and striped tie, with khaki wide-leg trousers, for Tommy Hilfiger's spring 2027 collection
A model in a green cap and blazer over a striped wordmark polo, with khaki trousers, for Tommy Hilfiger's spring 2027 collection
A model in a plaid trench coat over a colorblock wordmark polo, with khaki shorts and brown loafers, for Tommy Hilfiger's spring 2027 collection
A model in a plaid bucket hat and patchwork plaid overshirt, with pinstripe shorts and white sneakers, for Tommy Hilfiger's spring 2027 collection
A model in a tartan plaid jacket over a striped shirt and knit tie, with shorts and brown loafers, for Tommy Hilfiger's spring 2027 collection
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