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Jonathan Bailey's style file: Outfit choices that make him the sexiest star

We decode Bailey's latest style outings. 

Updated on: Nov 13, 2025, 16:34:13 IST
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Jonathan Bailey's devastatingly gorgeous face can make any outfit work in his favour. That said, the 37-year-old has a knack for stylish clothes and knows what works best on him. We decode his recent appearances to find out what worked and what didn't for the 'Most Stylish Man Alive'.

All eyes on Jonathan Bailey.
All eyes on Jonathan Bailey.

Monochrome magic

His latest look is a masterclass in winter layering.
His latest look is a masterclass in winter layering.

Attending the premiere of Wicked for Good, Jonathan Bailey made a case for winter layering in a gray wool button-down and matching trousers. He layered the look with a black coat and a red flower pinned to his lapel in honour of UK holiday Remembrance Day. The trousers were tapered at the ankle, adding a fresh touch to the look.

The new formal

Jonathan Bailey at the premiere of Jurassic World Rebirth.
Jonathan Bailey at the premiere of Jurassic World Rebirth.

Bailey wore a bomber-styled jacket with collarless neckline over a white tank top. He paired the look with high waisted pants. The star of the look are the Tabi mules. The split-toe style of the shoes instantly draws attention.

Rethinking separates

The dandy star has a thoughtful wardrobe.
The dandy star has a thoughtful wardrobe.

Bailey opted for a blue denim shirt, paired with white denim pants and layered it with a cocoa brown blazer and baseball cap. This is the elevated uniform for a man who understands that true style is about attitude and juxtaposition. It’s the preppy structure of the blazer, softened by the ruggedness of the denim and the casual punch of the baseball cap—a flawless expression of smart casual for the modern era.

Coffeecore

The actor blended relaxed aesthetic with rich colour and luxurious texture. He nailed the coffeecore trend with this look and the pleated pants look uber-chic. He finished off the resorty vibe with a pair of circular sunnies.

Indian at heart

Jonathan Bailey nailed the traditional look.
Jonathan Bailey nailed the traditional look.

Bailey left the Indian girlies swooning as he attended an Indian wedding wearing a crisp white kurta-pyjama set with a sky blue Nehru jacket. He accessorized the look with a pair of glasses on a cord around his neck. His Indian look went viral instantly.

  • Akshay Kaushal
    ABOUT THE AUTHOR
    Akshay Kaushal

    Akshay Kaushal writes on fashion, for the daily Entertainment & Lifestyle supplement, HT City.