Kylie Jenner and Timothée Chalamet have been one of the most fashion-forward couples to watch, and their June 17 outing in New York City was no exception. The pair was spotted cycling through Manhattan on Citi Bikes just one day before the New York Knicks' highly anticipated championship parade, and as expected, the internet had plenty to say—mostly about Jenner's shoes.
This was not your average celebrity sighting. Between the setting, the timing, and the footwear, the afternoon bike ride turned into a full-blown celebrity style moment that perfectly captured where streetwear trends are heading in 2026.
The Outfit That Stopped the Internet
Jenner kept things monochromatic and sharp for the outing. She wore black linen trousers, a black GUIZIO Perfect Classic Tank top priced at just $38, retro sunglasses, and a bamboo-handle handbag. The look was effortless and minimal, the kind of outfit that looks like it took no effort but actually requires a very specific eye for proportion and detail.
But the real talking point? Her shoes.
Rather than reaching for sneakers like most people would before hopping on a bike, Jenner chose Maison Margiela Tabi Ballerina Flats, priced at $1,050. The choice was unexpected, divisive, and entirely on-brand for someone who has made fashion-forward footwear a signature part of her celebrity style. As Who What Wear noted, the flats were "practical enough for pedaling yet still true to her luxe personal style."
Chalamet, who is a born-and-bred New Yorker, kept his look relaxed with a grey T-shirt, basketball shorts, and a New York Yankees cap. The contrast between the two outfits said a lot: one half of the couple dressed like he was heading to a pickup game in the park, and the other half dressed like she was walking out of a fashion editorial.
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What Makes Maison Margiela Tabi Flats a Streetwear Staple
The Tabi shoe has a history that predates Instagram, TikTok, and even Kylie Jenner's entire career. The design traces back to 15th-century Japanese split-toe socks, but it was Maison Margiela who introduced the style to the fashion world at his 1988 debut show, sending models down the runway in split-toe boots that left distinctive red hoofprints on the floor.
Since then, the Tabi has evolved into one of fashion's most recognizable and debated silhouettes. The split-toe design divides opinion almost everywhere, but that is exactly the point.
What has kept the Tabi relevant across decades is its ability to sit at the intersection of comfort and conceptual fashion. The split-toe construction is said to improve balance and grip, making the shoes surprisingly wearable despite their avant-garde appearance. Fashion insiders have long described the Tabi as a kind of secret handshake among people who understand the codes of high fashion: subtle to outsiders, instantly recognizable to those in the know.
Why Celebrities Cannot Stop Wearing Tabis in 2026
The Tabi moment happening right now in celebrity style is not a coincidence. In the weeks surrounding this bike ride alone, Laufey, Blackpink's Rosé, Zoey Deutch, and Zendaya were all spotted wearing variations of the split-toe silhouette. Post-Met Gala, Zendaya and Emma Chamberlain were both photographed in Tabi flats the morning after the event, choosing them over the heels they had worn on the carpet.
Jenner herself has been a Tabi loyalist for some time. She wore them on repeat during Coachella 2026, and the bike ride look marks yet another moment where the flats made the outfit rather than simply completing it.
The broader shift happening in streetwear trends is worth paying attention to here. Fashion-forward dressers are increasingly swapping out their sneakers for designer flats, especially the Tabi. Charli XCX was recently photographed traveling through Heathrow Airport in Maison Margiela Tabi flats as part of a polished all-black travel outfit, choosing them specifically over athletic shoes. The message is clear: in 2026, the Tabi flat is what the white sneaker was a decade ago.
Maison Margiela is leaning into this momentum. At the brand's Fall 2026 show in Shanghai, the label doubled down on the Tabi with new iterations including second-skin ballerina versions and stiletto-heeled Tabi-claw boots, signaling that the split-toe era is nowhere near its end.
Kymothée's Style Evolution: A Pattern Worth Noting
This bike ride did not come out of nowhere when it comes to the couple's fashion choices. Jenner and Chalamet have steadily been building a shared aesthetic identity that blends his downtown New York sensibility with her California-bred luxury instincts.
At Game 4 of the NBA Finals on June 10, the couple coordinated in matching denim looks featuring Chrome Hearts designs. Before that, they turned heads at the premiere of his film "Marty Supreme" in coordinated leather outfits, with Jenner in a fur-trimmed biker jacket and Chalamet in head-to-toe black leather with suede boots. The couple also made waves at the "Marty Supreme" Los Angeles premiere in custom Chrome Hearts orange looks.
Each public appearance adds another layer to what has become one of the more stylistically interesting celebrity pairings in recent memory. He leans effortlessly into New York street culture; she brings the elevated, designer-forward choices. Together, the looks tend to generate significant traction because they feel real rather than staged.
When Celebrity Style Shapes What Everyone Else Wants to Wear
Moments like Jenner's bike ride matter because of how quickly they move from paparazzi photo to shopping cart. The Maison Margiela Tabi Ballerina Flats have a well-documented history of selling out after celebrity sightings, and Jenner's outing is the kind of organic placement that money cannot buy.
More broadly, the look she put together that afternoon reflects exactly where streetwear trends are in 2026: minimalist, monochromatic, built around one statement piece, and entirely unbothered about being dressed up for a casual activity. The formula is simple to describe and difficult to execute, which is why it keeps producing moments worth talking about.
A $38 tank top, black linen trousers, and a pair of $1,050 split-toe flats on a Citi Bike in Manhattan. That is the outfit. That is the story.
