Jonathan Anderson’s Best Fashion Moments Over The Years
From the debut of Loewe’s Puzzle bag to the crystal rope bras for JW Anderson

Though the whispers had been circling for months, the fashion world is a-buzz over Monday’s confirmation that Jonathan Anderson, the Irish-born designer known for his cerebral yet often playful approach, will officially succeed Maria Grazia Chiuri as the new creative director of Dior across all categories. He’s spent the past 11 years transforming the Spanish house Loewe into a cult-favorite brand, which will now be helmed by designer duo, Jack McCollough and Lazaro Hernandez, the duo formerly behind Proenza Schouler.
In Anderson's new role, he’ll oversee women’s, men’s, and haute couture collections. This is a rare, sweeping appointment that marks a pivotal chapter for the house, with Chiuri’s role as the former creative director at the maison was confined to haute couture, ready-to-wear, and accessories collections at Dior, with Kim Jones helming menswear. While he's taking the reins at Dior, it's worth noting that there has been no announcement that he’ll step away from his namesake label, JW Anderson. Before he ushers in his Dior era, we’re taking a moment to revisit some of Anderson’s most unforgettable contributions to fashion over the years at JW Anderson and Loewe.
During Anderson’s tenure at Loewe, the house found a new rhythm shaped by his playful avant-garde sensibility, surrealist flourishes, and a penchant for sculptural, often geometric silhouettes. A defining moment came early on with the Fall/Winter 2015 collection, when Anderson introduced the now-iconic Puzzle bag, which celebrates its 10-year anniversary this month. The deconstructed take on the handbag was not just a first for Anderson, but the house as well, as the first new bag silhouette to be introduced since the 1980s.
Over the years, Anderson has proved that he’s never one to shy away from boundary-pushing silhouettes, imagining experimental collections where nature came alive with pieces like his unforgettable JW Anderson pigeon clutch from his Fall 2022 menswear show, that Sarah Jessica Parker’s Carrie Bradshaw wore in the filming of And Just Like That…, along with Loewe’s grass garments in 2022 and anthurium breastplate blouses in 2023. All of which challenged the idea behind art as fashion and how it pertains to human relationships with earth. Beyond the shows, his designs left a distinct imprint on pop culture, from custom tennis core looks for Zendaya’s Challengers press tour to Rihanna’s instantly iconic Super Bowl performance ensemble.
Elsewhere, at JW Anderson, the designer leaned into his signature experimental and genre-bending style when he sent crystal rope bras down the Spring/Summer 2020 runway over draped silhouettes. At the Milan Menswear Fall/Winter 2023 runway, Anderson took it one step further when he introduced pillow clutches as accessories, a plush cushion nearly identical to your bedroom necessity. Its absurdity marked a moment where fashion met function, with Anderson particularly questioning the zeitgeist’s understanding of where style and comfort meet.
Ahead, a few of our favorite Jonathan Anderson fashion moments over the years, before his Dior debut later this month.
The Puzzle Bag
Catwalking / Getty Images
Jonathan Anderson first introduced the Puzzle bag in Loewe’s Fall/Winter 2015 collection, which took place at the Unesco HQ in Paris. Apart from its innovative, geometric shape, unique materials, and quality craftsmanship, this piece marked an exciting shift for both the brand and former creative director as it was Anderson’s first handbag creation for the brand and Loewe’s first new bag to launch since the 1980s.
Crystal Rope Bras
WWD / Getty Images
At the JW Anderson Spring/Summer 2020 show, Anderson debuted a series of crystal rope bras as accessories, which sat atop flowy silhouettes and draped dresses, symbolizing the idea behind dualities that have the ability to be congruent, like softness and strength or fashion and armor. Perhaps a precursor to Anderson’s Loewe balloon bras.
Met Moments
Jamie McCarthy / John Shearer / Angela Weiss / Getty Images
During the 2024 Met Gala, Anderson dressed Ayo Edebiri, Ariana Grande, and Taylor Russell in swaths of pearly white and 3D illusions. From Edebiri’s blooming floral skirt to his wood corset top for Russell—who made her debut on the carpet that year—Anderson’s whimsical creations honored ‘The Garden of Time’ dress code.
Pin Dress
Pascal Le Segretain / Getty Images
This floor-length, butter yellow gown from Loewe’s Spring/Summer 2024 ready-to-wear collection featured a giant dressmaker pin pierced into the fabric near the décolletage, paying homage to the designer’s surrealist vision.
Organic Fabrics
Xinhua News Agency / Getty Images
In Loewe’s Spring/Summer 2022 Menswear Collection, Jonathan Anderson explored the fusion of fashion and nature, featuring garments and accessories being overtaken by authentic grass sprouting from seemingly sodden fabrics, which he achieved with the help of Spanish, sustainable designer Paula Ulargui Escalona. In Paris, the two designers grew chia plants and catswort for a span of 20 days to reach the desired growth, then integrating them into the collection as though the greenery grew around and atop the clothing to show the intersection of fashion, humanity, and sustainability.
Zendaya’s Tennis Attire for Challengers
Daniele Venturelli /James Gourley / Getty Images
On the press tour for Challengers, Zendaya wore two custom Loewe looks complete with tennis ball heels and interpretive takes on the traditional tennis dress.
Pillow Accessories
Daniele Venturelli / Getty Images
At JW Anderson’s Milan Menswear Fall/Winter 2023 runway, the designer leaned into the avant-garde as he sent models down clutching puffy pillow clutches to their person—a rather polarizing accessory that was intended to blur the lines between fashion and function, showcasing how style and comfort can work in tandem.
Loewe Fall/Winter 2024 Collection
WWD / Getty Images
After Anderson learned that Jackie Kennedy Onassis collected Albert York paintings, the Loewe Fall/Winter 2024 collection was born. The designer played on the notion of class, wealth, and the significance that high society bestows on artifact, producing unforgettable pieces on the runway, like the architectural, dog-printed A-line dress meant to parallel the mosaic rings of the elite, which often featured their pets.
Loewe Spring/Summer 2023 Collection
Estrop / Getty Images
Loewe’s anthurium collection saw walking surrealism, with flora and fauna breastplates and heels, as well as pixelated pieces that blurred the lines of fashion and art.
JW Anderson x Michael Clark Collab
Victor Virgile / Getty Images
In 2023, Anderson’s JW Anderson collaborated with dancer and choreographer Michael Clark on an exclusive Fall/Winter 2023 collection highlighting British culture for London Fashion Week. There were bold graphics, rhinestone-embellished knits, exaggerated sleeves, check suiting and quippy placards along the tops that read, ‘WITCH,’ ‘DENTIST’ and more
The Comic Lacquered Pumps (Spring/Summer 2023)
Victor Virgile / Getty Images
Anderson leaned into surrealism once again with the debut of the Comic Lacquered pumps in the Loewe Spring/Summer 2023 collection. The larger-than-life footwear had an exaggerated chunky design that instantly felt like it was plucked from Barbie’s wardrobe.
Rihanna at the Super Bowl LVII
Kevin Mazur / Getty Images
Rihanna wore a bright red, custom Loewe ensemble during her 2023 Super Bowl halftime performance, featuring Anderson’s signature balloon-like campy breastplate that complemented her pregnancy announcement.
Anya Taylor-Joy in a Modern-Day Victorian Dress for Emma
Sean Zanni / Getty Images
For the 2020 press tour of the film adaptation of Jane Austen’s Emma, Anya Taylor-Joy showcased a sculptural Loewe dress, which reimagined Victorian fashion through its fabric, piping, and modern crinoline silhouette.
JW Anderson Men’s Fall/Winter 2015 Collection
Victor Virgile / Getty Images
JW Anderson's Men’s Fall/Winter 2015 collection drew inspiration from the 1950s through to the 1980s, showcasing exaggerated collars and cuffs, ultra-high waist pants with side slits along the hem, and blending the decades' references into an ambiguous aesthetic.
Dame Maggie Smith x Loewe Campaign
Juergen Teller/Courtesy of Loewe
Loewe's Spring 2024 pre-collection featured, then, 88-year-old actor Dame Maggie Smith, highlighting the timeless nature of style and paying homage to a British icon.