Chester Is the Gender-Bending Unicorn of Generation Whose Style Is Based on Jaden Smith and Harry Styles

HBO Max
HBO Max

You're watching HBO Max's Generation, right? Of course you are. The Daniel and Zelda Barnz directed show follows high school students exploring their sexuality and expressing themselves largely through what they wear. Chester is played by Justice Smith, who you might recognize from Paper Towns and 2020's All the Bright Places, in which he starred alongside Elle Fanning.

The 25-year old actor brings his character to life with the help of costume designer Shirley Kurata, who's behind projects like Selena Gomez's recent "De Una Vez" video. Kurata is an expert at curating wardrobes, which becomes clear as soon as you see how much stuff Chester wears, and he's just one of the seven core kids the series follows. But Kurata accurately describes Chester as the rainbow unicorn of the show. He's inspired by 19-year-old Zelda Barnz's real life classmate, so his mood board started there, but also takes influence from Jaden Smith, Ezra Miller, Harry Styles, and the queens of RuPaul's Drag Race — specifically Yvie Oddly.

"His character doesn't come from a lot of money, but he is smart and resourceful and can make his outfits look great without spending a lot."

Even though shopping was tough during the pandemic (episodes are being filmed from September 2020 to present day), Kurata went online to thrift, mostly from the women's section, at local vintage shops, Depop, Etsy, Dolls Kill, and ASOS, stores Kurata felt like Chester would probably have his eyes on, along with eBay and Crossroads. "His character doesn't come from a lot of money, but he is smart and resourceful and can make his outfits look great without spending a lot," she told POPSUGAR, confirming that she was also sure to mix in LGBTQ+ sources such as L.A.G. vintage, anti-waste, gender-free label Official Rebrand, and musician/artist Seth Bogart's brand Wacky Wacko.

Kurata and Justice collaborated on the character completely. "Justice definitely played a part in how Chester would look. We would discuss what look would be appropriate for each scene — whether it would be a bit more masc-presenting or more gender-bending. We would collectively decide on what jewelry he would wear and how much he would wear," Kurata said. Ahead, the talented stylist shares behind-the-scenes fitting photos of Justice as Chester, which provide a sneak peek at the outfits we'll see him in soon, along with everything you'd ever want to know about how Chester's traumas and experiences impact who he is and what he wears. And yes, the iconic rainbow crop top from episode one is involved, because we know you can't get enough of it.

Justice Smith's Favorite Chester Outfit
Courtesy of Shirley Kurata

Justice Smith's Favorite Chester Outfit

"[Justice] loved the first outfit he wore in the first episode, but he calls this outfit — that hasn't aired yet — his favorite. It consists of a vintage jacket I found at Bearded Beagle, a vintage turtleneck from Cannonball & Tilly, and a pair of paper-bag waist women's jeans from Virgo, which is a downtown store that carries both new and vintage clothes."

Justice's Fittings For Chester
Courtesy of Shirley Kurata

Justice's Fittings For Chester

"Fittings for Chester are superfun because we can go in so many directions for him. With each outfit, we start adding accessories, and Justice is always saying, 'More! More!' With Chester, it's not less is more, it's more is more! In terms of showing skin, Chester is all about showing more skin."

Courtesy of Shirley Kurata

"Justice's personal style is different from Chester's, so he didn't bring anything of his own to set. They are two different people, which is a testament to how great an actor he is. Once Justice was dressed as Chester, he would be Chester; even off-camera he would wear a face mask that would match his outfit, or have a comfort coat that was bedazzled in Chester fashion."

Chester's Iconic Tube Top Moment
HBO Max

Chester's Iconic Tube Top Moment

"Daniel and Zelda Barnz, the creators of the show, had written in the script that Chester wears a red tube top to school. I had tried some on him, but after seeing this rainbow crop top on him from Dolls Kill, I felt that it would be a better statement than the red tube top. Also, right now in women's fashion, crop tops are superpopular and Chester would naturally gravitate toward that given his gender-bending inclinations."

How Chester Stands Out
HBO Max

How Chester Stands Out

"Chester [was] the one unicorn that would stand out and push the boundaries more."

"For the pilot, which was filmed pre-pandemic, I would drive by the high school near my house and study what the students were wearing when school was out. Unfortunately, we were shooting the rest of the season during the pandemic, so I wasn't able to study kids out and about as much. I studied a lot of YouTube videos posted by high school students interviewing other students about their outfits. I wanted to make sure the rest of the cast reflected as closely to what teenagers are wearing today, with Chester being the one unicorn that would stand out and push the boundaries more. The other characters still had their own style but more scaled down and less accessorized. It was important to keep a nice balance to make it real and believable."

Chester's Jewelry
HBO Max

Chester's Jewelry

"The jewelry is a mix from a lot of places. A good number are handmade pieces from independent Etsy and Depop vendors and the Slauson Swap Meet. I also sourced from online vendors like Dolls Kill and ASOS, The Santee Alley, flea markets, vintage stores, and local jewelry shops like Maya. They are fun, but also pretty inexpensive."

Chester's Grandma Influence
HBO Max

Chester's Grandma Influence

"Chester's mother passed away, so he lives with his grandmother, and she's the type that never throws anything out, so I wanted to put him in stuff from his grandmother's closet — pussy-bow blouses, pearl necklaces, and vintage floral cardigans that she wore when she was younger. I did that with my mother's closet, and I think Chester would do the same!"

How Chester's Style Reflects His Mood
HBO Max

How Chester's Style Reflects His Mood

"Chester's style changes based on his moods. When he's listening to Britney Spears, he amps it up. When he's depressed, like in episode eight, he wants to be unseen and dresses in gray. We also choose the underwear he wears for each episode, and they are purposely chosen to go with his outfits."

Chester's Pink Hair Moment
HBO Max

Chester's Pink Hair Moment

"When I found out Justice was going to have pink hair for episode four, I felt like he would wear an outfit to match his hair. I found a pink short-sleeved shirt for him, and Justice was like, 'Chester likes to show his skin, so he would make this shirt sleeveless and tie it up so it's cropped.' So, we removed the sleeves and then went into the process of accessorizing. My assistant costume designer Minnie Garcia found this pink bunny backpack at the Slauson Swap Meet, and we all felt Chester needed to wear it. We piled on the accessories, and when Justice showed up on set, Daniel Barnz saw him and was like, 'He looks too much like he's on the runway and less like a teenager,' so we had to tone down the accessories. But Justice and I were like, 'The bunny needs to stay!'"