As Jonathan Bailey glides across red carpets promoting Wicked this week, it’s clear the British actor has mastered more than just hitting his marks. Already earning rave reviews for his portrayal of Fiyero in the highly anticipated film adaptation, Bailey has simultaneously emerged as one of Hollywood’s most intriguing new style forces—a leading man whose sartorial choices are as bold and nuanced as his acting range.
The 36-year-old Brit’s fashion evolution mirrors his meteoric rise from stage actor to global star. While he initially caught attention as the brooding Anthony Bridgerton (a role he confirms he’ll reprise in season four, albeit in a reduced capacity), it’s his confident red carpet appearances that have cemented his status as a male style icon. Whether sporting perfectly tailored Gucci suits or experimental Loewe ensembles, Bailey brings a dancer’s physicality and theatrical flair to menswear that feels both classic and distinctly modern.
His approach to fashion reflects his wider artistic philosophy—one he tells IndieWire rooted in early years as “the only boy within whatever-mile radius” at dance class. That same willingness to stand out and embrace personal expression now manifests in his wardrobe choices, from statement outerwear to adventurous proportions. Living in seaside Hove, where he starts each day with an invigorating swim, Bailey maintains an effortless balance between polished leading man and artistic free spirit. As he steps into even bigger spotlight with Wicked and the upcoming Jurassic World: Rebirth, his thoughtful approach to style continues to evolve, proving that the most compelling fashion wins come from a place of authentic self-expression.
Baby Bailey serves up serious charm in a Lacoste polo that’s more art gallery than tennis court. The whimsical print turns sportswear into conversation piece, while that perfectly coiffed hair suggests a star in the making. Consider this the prequel to his style saga—before the designer suits, but already showing signs of the fashion rebel to come.
Consider this Bailey’s red carpet training wheels—and what a ride. The slim-cut three-piece suit gets a moody upgrade through dark-on-darker layering, while those burgundy socks hint at the style maverick waiting in the wings.
Before he was breaking hearts in Netflix’s Bridgerton, Bailey was breaking the rules of business casual. That butter-yellow Oxford paired with perfectly tailored navy chinos shows an early knack for color play.
Who knew workwear could be this playful? Bailey transforms into an urban cowboy in honey-colored corduroy and tropical prints, proving that sometimes the best costume is just elevated everyday wear.
Bailey channels peak varsity charm in a color-block rugby that screams “prep school rebel with a cause.” Those pristine white kicks and perfectly worn-in denim prove he understood the assignment: young Hollywood with a British twist.
Courtside style gets an upgrade with tonal blues and perfect proportions from Lacoste. The knit polo and tailored trousers hit the sweet spot between casual and considered—exactly the kind of effortless polish that’s become Bailey’s signature.
Between shows in Milan, Bailey demonstrates the power of considered basics. A navy button-down shirt tucked into black trousers creates a clean line, while white sneakers with navy accents show his eye for subtle coordination.
At the Ami show, the English actor channels French minimalism with razor-sharp execution. The leather overshirt adds subtle luxury while hitting the sweet spot between workwear and avant-garde. Doc Martens and high-waisted trousers complete a look that feels equally at home in Le Marais or on set.
Pure sophistication in Givenchy—a winter white suit with considered proportions. The wide-leg trousers and crisp button-down demonstrate Bailey’s understanding of modern formal wear, while black loafers ground the monochromatic statement.
A slam-dunk example of tonal dressing at the Burberry (BURBY) fashion show, the cream trench’s architectural shoulders complement the relaxed grey suit beneath. Wide lapels and fluid trousers speak to current trends while maintaining timeless appeal.
A Loewe confection that nods to his Wicked character Fiyero—the white trousers and iridescent blue top create ethereal movement while maintaining masculine edge. The combination shows Bailey’s comfort with theatrical elements in daywear.
Cable knit complexity: Bailey layers texture masterfully with a chunky cream sweater over crisp cotton. The interplay of casual knitwear with sharp shirting showcases his skill at high-low dressing.
Custom Loewe brings architectural drama to the museum steps. The double-breasted white suit jacket creates a canvas for the showstopping oversized floral embellishment—a masterclass in statement dressing that honors the “Sleeping Beauties” theme.
Giorgio Armani’s impeccable tailoring provides the foundation, but it’s Bailey’s styling choices that elevate this look at the television awards show, for which he was nominated for Best Supporting Actor for his role in Fellow Travelers: the strategic shirt unbuttoning, the De Beers gardenia brooch placement, and those tinted sunglasses. This is how you make black tie feel fresh without losing its essence.
In Giuliva Heritage’s perfectly proportioned shorts and sheer polo for a Wicked promo in Australia, Bailey proves that formal doesn’t always mean full-length. The high waist and precise pleating maintain sophistication while embracing modern menswear’s more relaxed direction.
Bailey demonstrates his flair for dramatic eveningwear in a Loewe ensemble with a metallic chainmail shirt that plays with texture and transparency. The pairing with crisp white trousers creates a striking contrast, while ruby Versace footwear adds theatrical punch without crossing into costume territory.
For the Wicked premiere with co-stars Ariana Grande and Cynthia Erivo, Bailey opted for Givenchy from head to toe: burgundy blazer, white tank and an unexpected purple cummerbund. The sunglasses-at-night move? Pure star power.
Even in athleisure, Bailey’s eye for proportion and color shows through. The oversized puffer balanced against fitted sweats creates a considered silhouette, while the bold yellow-navy palette demonstrates that casual doesn’t mean careless.
Loewe’s innovative hand-torn silk detailing elevates a classic suit silhouette into contemporary art territory. The textural play creates depth and movement, while Chelsea boots and an Omega timepiece ground the look in masculine utility.
007 meets musical theater in a Ralph Lauren Purple Label tuxedo—a cream double-breasted dinner jacket that had everyone shaken and stirred.
