“Is there a prize for the stupidest outfit at Men’s Fashion Week in London…? If so, one of these must be the winner.”

The headline, published in the Daily Mail in 2013, ran alongside several photos from the JW Anderson Fall/Winter 2013 collection during London Fashion Week. The collection showcased ruffled shorts, dresses, bandeau tops, and riding boots worn by male models.

“At J.W. Anderson, the humiliation of the models was made truly complete as the designer sent out his clan of put-upon male beauties wearing frilly shorts, leather dresses and frill-trimmed knee-length boots,” the article read.

To this day, the show stands out in Jonathan Anderson’s memory. “I just saw it as a normal show, and the message was a gender- fluid, shared wardrobe. But the next day, the Daily Mail was scandalized. They said we’d humiliated the models, fashion, masculinity as a whole,” he recalled.

“When you look back, it’s crazy how far we’ve come in less than a decade, you wouldn’t be able to write that today.”

Today, this very collection is now on display in museums around the world.

It’s safe to say Anderson was ahead of his time. Nowadays, the cultural landscape has shifted greatly. Popstar Harry Styles graced the cover of American Vogue wearing a floor-length ball gown; Oscar Isaac wore a skirt while on a recent European press tour; and Timothée Chalamet showed up to the Venice Film Festival wearing a backless halter top. Each was praised for their daring fashion choices.

Thankfully, such criticism didn’t get him down. Anderson persevered and has since become one of the most celebrated and recognized designers in the world. This year, he is adding the CFDA’s International Designer of the Year Award to his accolades for his work at JW Anderson and the Spanish luxury house Loewe.

It’s a full circle moment of sorts for the Irish native, who moved to Washington D.C. as a teenager to attend the Studio Theatre and pursue his interest in acting, and discovered his love of fashion during that time.

“While I was there, I met this incredible guy who was in charge of costumes at the theatre. I spent lots of time with him instead of going to rehearsals, and he taught me everything important about American designers,” Anderson recalled. “He ignited that passion in me. I was working on ‘A Midsummer’s Night Dream’ and became obsessed with the costumes and this idea of characters and clothing.”

Anderson returned to Ireland and landed a job at a luxury Irish department store Brown Thomas. After moving to London to attend London College of Fashion, where he graduated in 2005, he was hired by Manuela Pavesi to work as a visual merchandiser at Prada, where he spent nearly two years. Anderson took a leap of faith and in 2008 launched his own label, JW Anderson. He quickly garnered attention for his buzzworthy, fashion-forward,and controversial collections. His work caught the attention of Delphine Arnault and then LVMH-executive Pierre-Yves Roussel, who approached the designer to buy a minority stake in his label – and also came with another idea. They pitched Anderson with the prospect of taking over Loewe.

“They were like, ‘Why don’t you go to this factory?’ And I said, ‘Sure, why not?’ So, I remember going to the factory in Spain pretending I was writing for a magazine. Undercover. I’ll never forget the day I turned up, going into a room filled with all different leathers. I was just like, ‘This is the brand I want to work for.’ I created a kind of scrapbook of ideas, and I presented it to them.”

The bet paid off, and under Anderson’s leadership, Loewe has become one of the hottest fashion brands in the world on track to become a $1 billion brand by 2024. His own label has seen similar success.

Upon first glance, it’s not quite clear why. Anderson frequently bridges the worlds of art and fashion, drawing inspiration from other mediums like poetry, pottery, sculpture – into designs that are innovative and inspiring, but not exactly commercial.

At Loewe, Anderson tapped a young artist Paula Ulargui Escalona for the Spring/Summer 2023 collection that explored the relationship between nature and technology. Live grass sprouted from garments and footwear on the runway, each of which required regular watering to maintain proper health of the plants for the show. At JW Anderson, he presented clay molded hoodies and shorts in bright colors for the Spring/Summer 2024 show, which sat in rigid forms on the body.

Anderson’s brilliance lies his ability to inspire and excite audiences with beautifully strange clothing that sits just in the sweet spot of avant-garde and wearable. Across both Loewe and JW Anderson, an element of familiarity and nostalgia keeps you just invested enough to want to buy into the world he is selling.

Of course, it doesn’t hurt that the brand has also garnered massive support from a roster of A-list clientele. In the last year, Anderson created custom looks for Rihanna’s Superbowl performance and Beyoncé for her Renaissance tour. In 2020, Harry Styles helped JW Anderson go viral on TikTok when he wore a patchwork cardigan that fans began to recreate at home. Inspired by their creativity and craft, Anderson released a Knit Pattern for sale through the brand. “I am so impressed and incredibly humbled by this trend and everyone knitting the cardigan. I really wanted to show our appreciation so we are sharing the pattern with everyone. Keep it up!” he wrote on the brand’s website.

Anderson has long had an appreciation and dedication for artistry and craft, perhaps most evident through the Loewe Craft Prize, started in 2018 to celebrate excellence in craftsmanship. Anderson also sits on the board of the Victoria & Albert Museum in London.

Despite the striking similarities between the two, Anderson manages to make the two labels feel distinct from one another, which he largely attributes to the brand’s separate home bases – and the teams that operate them (JW Anderson is based in London and Loewe in Paris).

“I have this thing that when I go through the tunnel on the Eurostar, I’m in a different landscape. The two cities are so incredibly different culturally and there are two different teams. So, when I am there, I am 100% there, and when I am at JW, I am 100% here,” he said.

“There might be threads between them. I can’t do one fashion show and then say two weeks later that everything that was done then is irrelevant. It is kind of about building two different languages. That idea of JW as a cultural agitator; I think there is a youthful friction in it that it is more naive, more crafty, less refined. And then at Loewe you’ve got the weight of a leather house, and everything is bigger. Ultimately there is a thread, there is an ‘I’, but I think the biggest thing is having two very distinct teams that you have two dialogues with. I can’t do what I do without having some of the best people in the world to work with. I feel that sometimes I am a director, or a conductor,” he added.

The weight of running two luxury houses in an industry as demanding as fashion is an impressive feat. Yet the pace has not seemed to dampen Anderson’s creativity. Anderson credits his innate sense of curiosity for his continued drive.

“I know that if I lose curiosity, creativity and inspiration go away. I have to absorb everything around me in real time to predict the future since I’m supposed to imagine what will be in stores in six months,” he said. “Concretely, I listen to podcasts and I read the press religiously for two hours, every morning, to be aware and try to understand what is happening in the world. I can’t live in a bubble. Because how could I dress society if I am not aware of what crosses it?”

Even now, Anderson finds new ways to push himself. The designer will be returning to his film roots by taking on the job of costume designer in the upcoming Luca Guadagnino film, Queer.

“I really enjoyed it, but I wouldn’t do this for anyone but Luca,” Anderson admitted. “It gave me a deep appreciation for the work film costume designers do. The movie is set in the past, but it’s not theatrical at all, so the challenge was to try to make something look as real as possible.”

Anderson’s career is one any aspiring fashion designer would admire. Achieving commercial success and critical acclaim at such a young age, Anderson has earned his title as a wunderkind of the industry. We now live in an era where the visibility of fashion designers is greater than ever, with designers becoming celebrities in their own right – and this type of attention can be daunting to even the most seasoned designer. Yet even as his profile has grown, Anderson has managed to keep his head down and focused on the job.

“Fashion is all about hard work,” he said.  “You can have all the talent in the world, but if you are not willing to commit to that marathon, then it will not work. And another thing is that you cannot go into fashion as a fame game.”

The CFDA Fashion Awards presented by Amazon Fashion will take place on Monday, November 6th at the American Museum of Natural History.