Timothée Chalamet and Kylie Jenner seem to be going stronger than ever.
From attending awards shows together to sharing photos from a private beach vacation, the couple has been inseparable for much of the year. On Wednesday, they sat courtside at a Knicks game, kissing in between plays and grinning at each other.
Jenner and Chalamet were first linked in 2023, and though they keep their relationship largely private, they tend to make a fashion statement whenever they do step out together.
Here are Jenner and Chalamet’s style moments as a couple, ranked from worst to best.
Jenner and Chalamet’s styles clashed at a tennis match in March 2025.
Jenner and Chalamet both wore casual attire when they attended the BNP Paribas Open in March 2025, but Chalamet opted for a sporty look, while Jenner chose a retro-inspired style.
Jenner wore white pants and a red Celine top. She paired the look with round Courrèges sunglasses, completing the retro ensemble.
Chalamet, on the other hand, wore a white Adidas jacket with green detailing and a Saint-Étienne logo. Both looked relaxed and stylish, but their outfits didn’t work as well together.
Their style also seemed out of sync at the 2025 Academy Awards.
Though they didn’t walk the red carpet together, Jenner accompanied Chalamet to the 2025 Oscars.
Chalamet turned heads in a leather, butter-yellow suit from Givenchy, which he accented with a bejeweled pin on his neck and gold accessories.
Jenner wore a custom black gown from Miu Miu. The bodice had bold cutouts on the waist, creating a bikini-style top adorned with sparkly gems that continued on the form-fitting skirt.
Again, both looked stylish, but it didn’t seem like they had given much thought to how their outfits might look together, given the stark color contrast between them.
They each leaned into their personal style for the 2025 Golden Globes.
Jenner dazzled in a silver vintage Versace gown when she attended the 2025 Golden Globes as Chalamet’s date. The dress scooped low on the neckline, had an open back, and was covered in silver sequins.
Chalamet paid homage to Bob Dylan with his outfit, as he was nominated for his performance as the singer in “A Complete Unknown.” He paired his sequin-adorned Tom Ford suit jacket and pinstripe pants with a thin blue scarf, one of Dylan’s signatures.
Their outfits looked great on their own, but it was clear the couple still hadn’t fully leaned into coordinated style yet.
Chalamet’s and Jenner’s relaxed looks for a Lakers game in April 2025 complemented each other.
The couple sat courtside at an NBA playoff game in April 2025, when the Los Angeles Lakers faced the Minnesota Timberwolves, and both wore black-and-white outfits.
Jenner wore a one-shoulder white crop top with black leather pants that had rips running down the front. Roberto Cavalli designed the edgy trousers.
Chalamet wore a tee featuring a black-and-white photo of Kobe Bryant, celebrating the late Lakers player. He wore a black-and-white-checked jacket from Chanel over the shirt, which he paired with black jeans and Timberland boots.
While Jenner’s outfit was sleek and Chalamet’s had a more playful feel, the coordinated colors made them look chic together.
Both of their outfits for the 2026 Critics Choice Awards had a retro flair.
Chalamet seemed to draw on “Marty Supreme” for inspiration with his look at the Critics Choice Awards in January 2026, wearing a navy pinstripe Givenchy suit that wouldn’t have looked out of place in the 1950s, when the film was set. He paired the classic suit with a multicolored floral tie and Chelsea boots.
While Chalamet’s look was vintage-inspired, Jenner wore an actual vintage Gianni Versace gown from 1996 to support Chalamet. The black sequin-covered gown hugged Jenner’s figure and featured sheer lace panels on the sides.
It was fun that Chalamet’s and Jenner’s looks both had a vintage flair, but they would have worked even better together if Jenner had looked to the ’50s for her ensemble to coordinate with Chalamet’s.
The couple’s ensembles for the 2026 Oscars were glamorous, but they didn’t look great side by side.
Chalamet, who was nominated for best actor for his performance in “Marty Supreme” at the 2026 Oscars, wore an all-white Givenchy suit to the awards show.
Jenner, meanwhile, sparkled in a red Schiaparelli keyhole dress with a plunging neckline that hugged her figure. It almost had a Jessica Rabbit feel.
Jenner and Chalamet could have gone for a retro, old Hollywood vibe together, but Chalamet’s styling didn’t do them any favors. His wide-legged pants and boots modernized his look too much.
The couple looked a bit mismatched at the Golden Globe Awards in January 2026.
Chalamet wore Chrome Hearts to the January 2026 Golden Globes, where he won best actor for his performance in “Marty Supreme.”
The all-black look put a casual spin on red-carpet attire, as Chalamet didn’t wear a tie and paired the suit with Timberland boots. A vest with silver buttons and a silver chain accented the ensemble.
In contrast, Jenner’s custom Ashi Studio Couture gown was as glamorous as they come. Made of silver sequins, the figure-hugging dress featured a sweetheart neckline, a corset bodice, and several spaghetti straps resting on her chest.
The couple both wore pretty ensembles, but they didn’t quite fit together. A slightly more formal suit from Chalamet would have taken their couple style over the edge.
Their after-party looks for the 2026 Vanity Fair Oscar Party felt more cohesive than their outfits for the ceremony.
They both changed their wardrobes after the 2026 Oscars for the Vanity Fair party.
Chalamet wore another monochromatic white look, turning to Chrome Hearts for the suit, which he wore with no tie, lace-up boots, and a chain.
Jenner arrived in another sparkly dress, this time a custom McQueen number. The gown had a halter neckline, a cutout on her waist, and a feathered skirt with a subtle train.
Both Jenner and Chalamet looked stylish and ready to party, making their looks a great fit for the Vanity Fair party.
The couple both wore all black at the 2025 BAFTAs.
Jenner’s and Chalamet’s coordinating black looks for the BAFTAs both had a chic feel.
Chalamet wore a Bottega Veneta suit with a T-shirt and black shoes, adding a high-end touch with Cartier jewelry.
Jenner chose another vintage look for the occasion, wearing a 1995 John Galliano semi-sheer gown with sparkly sequins. Strappy silver shoes, a messy updo, and diamond jewelry completed her look.
At their first awards show together in January 2024, they both wore sultry black looks.
Jenner first accompanied Chalamet to the January 2024 Golden Globes, though she didn’t walk the red carpet with him. The couple’s coordinating black looks were perfect for their first A-list event together.
Chalamet wore a sparkly black suit by Celine Homme, paired with a black shirt and a statement necklace. Jenner opted for a subtly sparkly Hanae Mori gown adorned with sheer cutouts and floral embroidery.
The textured looks paired well together for the event.
Jenner and Chalamet wore some of their most fun ensembles to date to Knicks games in 2025.
Jenner and Chalamet attended multiple Knicks playoff games in May 2025, and both rocked outfits supporting the New York team.
During game six of the Eastern Conference Finals, Chalamet repped his team in an all-orange look, pairing a Knicks-embossed jacket with coordinating pants featuring a blue stripe down the side, much like the team’s uniforms. Timberland boots and white sunglasses completed his over-the-top look.
Jenner kept her Knicks support slightly more subtle, pairing dark jeans and white pointed-toe shoes with a vintage Knicks jacket featuring blue, orange, and white stripes and the team’s logo. She also wore large hoop earrings, adding a bit of glam to the sporty look.
Their coordinating orange jackets for game five were perfect for the occasion.
Jenner and Chalamet’s looks for game five of the 2025 Eastern Conference Finals were just as festive but slightly more coordinated.
Much of Chalamet’s look was designed by Chrome Hearts, including his black jeans, black boots, and the custom Knicks varsity jacket that was the star of his ensemble. He wore a striped blue-and-orange shirt beneath the statement jacket and accessorized the look with a $11,000 Cartier necklace.
Like her partner, Jenner rocked an orange jacket with black pants. Her vintage Jean Paul Gaultier jacket featured white detailing, which she wore over a white top, and she paired it with 2001 Gucci pants. She also wore a statement piece from Cartier in the form of a $54,000 watch.
Chalamet and Jenner seemed to really find their groove as a couple with the look.
They brought back their coordinating sporty looks at a Knicks game in May 2026.
The pair watched the Knicks beat the Philadelphia 76ers on May 6, 2026, sitting courtside.
They coordinated their ensembles, with both wearing jeans, a simple top, and orange jackets. Jenner completed her look with orange-and-white Miu Miu heels and a navy Birkin bag, fully leaning into the Knicks spirit.
Their sporty style worked well together.
Their outfits for one of their first public outings as a couple at the September 2023 US Open also felt cohesive.
Chalamet and Jenner attended the 2023 US Open, making their relationship clear by kissing at the event.
Their outfits for the match were both simple and relaxed in the same style. Jenner wore a black T-shirt with Bottega Veneta accessories, including rounded sunglasses. Chalamet also wore round sunglasses, which he paired with a gray tee and black hoodie.
Chalamet’s and Jenner’s outfits looked cohesive together.
The couple’s casual ensembles for another Knicks game in April 2026 complemented each other.
The couple watched the Knicks beat the Hawks on April 28, 2026, and they both decided not to lean too heavily into Knicks attire for the game.
Chalamet wore wide-legged cargo pants, a gray tank, a hoodie with blue embroidery, and a black leather jacket.
Jenner went for an all-white look, pairing bedazzled Isabel Marant jeans with a white tank and Manolo Blahnik sandals. She also wore a black leather jacket during the evening.
The couple looked effortlessly cool as they roamed New York City together.
Jenner and Chalamet both wore sultry looks for the 2025 Vanity Fair Oscar Party.
Both Jenner and Chalamet had a wardrobe change for the 2025 Vanity Fair Oscar Party, and their post-ceremony looks suited each other much better than their looks for the awards did.
Jenner changed into a strapless Ashi Studio gown. The dropped-waist gown had a corset-style bodice that was semi-sheer with lace appliqué, and the mermaid skirt featured a layer of darker fabric.
Chalamet swapped his yellow look for a Tom Ford ensemble. His black jacket had subtle polka dots, while his black trousers were simple. He also wore his white shirt slightly unbuttoned.
Jenner’s and Chalamet’s looks had a sexy vibe, well-suited to the after-party.
Their monochromatic orange outfits for the “Marty Supreme” premiere created arguably their most memorable style moment to date.
Chalamet spent the months leading up to the premiere of “Marty Supreme” in an assortment of orange looks, nodding to a ping-pong ball in the film.
Those months of promotion seemed to come to a head at the premiere when Chalamet and Jenner arrived in custom all-orange ensembles from Chrome Hearts.
Jenner’s dress had a plunging V-neckline, mirroring the cutouts on either side of the bodice. The dress hugged her figure on the skirt, with a slit cutting up one side.
Chalamet paired his orange leather suit with Timberland boots and an orange shirt. He also carried a black paddle holder, cementing the celebration of “Marty Supreme.”
The looks were dramatic and playful, and they will certainly stand out in Jenner and Chalamet’s couple style history.
Their coordinating looks for the BAFTAs in February 2026 were among their best red-carpet looks to date.
Jenner chose a vintage look for the 2026 BAFTAS, accompanying Chalamet in a 1999 Mugler gown. The black dress had sparkly beading on the bodice, a fun touch she played up with big earrings.
Chalamet’s custom Givenchy suit was also black, paired with a black bow tie and dress shoes.
The couple looked moody and chic side by side in their complementary ensembles.
When Jenner and Chalamet made their red-carpet debut as a couple in May 2025, they knocked it out of the park with their complementary black looks.
Jenner and Chalamet walked their first red carpet together in May 2025 when Chalamet received an honorary award at the 70th David di Donatello Awards in Rome.
The couple wore coordinating black looks for the occasion. Tom Ford by Haider Ackermann designed Chalamet’s black velvet suit, which included a double-breasted jacket and flared pants. He wore a black shirt beneath it with no tie. A white flower on his lapel offered a pop of color.
Jenner’s Schiaparelli gown was textured, with a scooped neckline and crisscrossed straps in the back. She carried a black-and-gold Schiaparelli clutch and wore statement gold earrings.
The coordinating colors and similar high-end, fashion-forward feel of Jenner’s and Chalamet’s outfits were perfect for their red-carpet debut as a couple.
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