by Emily Maesar, Associate TV Editor

The things that make a movie are all the details that are often overlooked. Things like editing, music, production design, casting, and costuming. You can’t make a film without those elements, and the best films are showcases for them working in perfect harmony. Challengers, directed by Luca Guadagnino and written by Justin Kuritzkes is a case study in this. Particularly the costume design by Jonathan Anderson.

Anderson had never done costume design for a feature film, but he and director Luca Guadagnino met because of how much Guadagnino loved his collections. His history in fashion is a deeply interesting one, as he created his own label, JW Anderson, around 2008. In 2013, he was named as the creative director of Spanish fashion house Loewe, which has seen a fair amount of recent notoriety following Challengers, with many actors in the film becoming ambassadors for events in 2024. His understanding of brands and iconic silhouettes made him the perfect choice for the job.

Since its inclusion in the Oscars in 1949 for the 21st ceremony, the Costume Design award has gone to over 90 films. Which, if you’re doing the math, does mean there’s a bit of an incongruence between how long the award had been handed out and how many Oscar ceremonies there have been (we’re about to have our 97th ceremony). Until 1966, two Costume Design awards were handed out almost every year: one for black-and-white films and one for color. If you were to generally conceptualize what films would get this kind of Oscar, it makes sense that big period pieces or musicals with showy costumes would often win.

Since 2000, only two films set in the modern era, or even set within those 24 years, have won Best Costuming: Black Panther and Black Panther: Wakanda Forever, with costumes by Ruth E. Carter for both. While they’re contemporary films, they have very specific costuming that feels more in line with the epics that have won in the past, fitting nicely into the lineage. Since 2000, there have been less than ten films set within the 24 years between then and now that have even been nominated for Best Costuming. All of which is to say that there are few things harder to get Oscar recognition for than contemporary or recent period costuming. And, if it wasn’t obvious, I think Challengers is a truly great example of it—knocking its costumes out of the park.

Despite costumes being a very important part of the language of film, they are often overlooked, or even deemed as unimportant, by some audience members. However, to quote Luca Guadagnino from a W magazine interview he did with Jonathan Alexander, “The way a character looks does very much provide insight for an audience before anything is revealed through drama, interaction, or behavior on-screen.” You’re literally judging the book by its cover and costuming allows you have a little bit of a jump into that. It allows you to see things in a character you might not get through action or dialogue at any point in the film.

At a recent Q&A for Challengers, Anderson talked about how America is inundated by branding from the moment you step off a plane, especially in the sports world. Not to mention that sports stars themselves become brands. It was important to have that feel like an authentic part of the film and why Challengers not having any paid product placement allowed him the freedom to express things about the characters, and their status in life throughout the film, with their clothing. To quote Anderson from the Q&A, “There’s something quite psychological about that. Why we wear things and, as you get more successful, why you would buy something.”

For Tashi Duncan (later Donaldson), played by the iconic Zendaya, her fashion is deeply important to understanding how she moves through life. As an up-and-coming tennis wunderkind, she’s decked out in branding (including in Adidas adverts at the Junior US Open and Nike at Stanford) because that’s the name of the game for sports stars. Once her career is over, Tashi changes her life into something else and her clothing changes with it. When she becomes Art’s coach, and they visibly have money, her style becomes much more sleek and rich. With only things like her liquid-filled pink sparkly phone case and jewelry (including a Taylor Swift-style friendship bracelet with her daughter’s name on it) to give her real personality.

But, of course, there’s the blue dress. Oh, wait. Actually, dresses! Something that I think Anderson really knocked out of the park with Tashi’s clothing is this use of blue dresses in every era of her life, except for Stanford because the school’s color is red. You’ve got the strapless blue dress from the Adidas party that she wears, like a beautiful siren by the water. It evokes 2006 high school dance dresses, certainly. Then there’s the deeply period accurate blue silky dress from Applebee’s that, combined with the jacket and huge wedge heels, make this perfect recreation of a 2009 outfit, but it’s also giving “just a girl” energy in the scene. And then, of course, there’s the white and blue wrap dress she wears during the Phil’s Tire Town final that is the throughline of the whole film. All three are perfect time capsules, but also give you a lot of information about how Tashi sees herself and the image she’s projecting to the world.

Like Tashi, Art (Mike Faist) and his career is covered in branding. And because he’s a professional tennis player for longer than her, he remains branded. Between the Mark Rebellato Tennis Academy and Stanford shirts of his youth, the Nike branding before Tashi becomes his coach, and the Uniqlo branding later in his career, Art can be seen as nothing but a piece of advertising. “There is no aesthetic—it is just whatever is there,” said Anderson in the W magazine interview.

Then there’s everybody’s favorite rich kid, Patrick (Josh O’Connor). When Anderson was figuring out what Patrick’s style would be, he decided on American royalty: John F. Kennedy, Jr. While Patrick’s family history is only hinted at, it would make sense if his wealth came from a similar style of dynasty. That and, as Anderson said in the Q&A, “I wanted him to look like JFK Jr. because I think he’s the hottest guy in history.” So true! Which leads us nicely to the “I Told Ya” shirt. There are two things at play here with this shirt, so let’s discuss!

First, the history of the thing. When John F. Kennedy won the election in 1960, the pins for his inauguration read the slogan “I Told You So.” Cheeky, fun, and the sign of victory—without the knowledge of what was to come. That slogan was later transposed into the shirt worn by John F. Kennedy, Jr. during a park visit where he played frisbee. “I Told Ya,” was modern, still cheeky and fun, and deeply iconic. Having Patrick wear it is a really nice nod to his style inspiration and his generational wealth. Second, there’s the sharing of the shirt. Patrick isn’t the only one who wears it. First seen on Tashi, Patrick later takes the shirt when he leaves after their fight, before Tashi’s tennis career is over forever. He wears it again when they meet at the Atlanta Open. It becomes the symbol of something that ties them together across time, again without the knowledge of what was to come after each on-screen wearing.

The costuming in Challengers is specific, iconic, and beautifully executed. The film takes place between 2006 and 2019, and fashion changed so much over that time. Even since 2019! But while Jonathan Anderson captures the time periods with perfect precision, he’s also masterful at allowing the characters to speak for themselves with their clothing over the course of the most important 13 years of their lives. It’s more modern costume design with intent and no one’s done this specific type of design better than this—not for a long time.