Every year, major events like the Met Gala, Oscars red carpet, and Paris Fashion Week provide us with memorable style moments. We’re not even two full months through 2026 and the year has already provided us with a few that we will remember for the rest of the year.
We started off the year with a bang when Trax NYC got into a brawl in the Diamond District. The Pope got blessed with some Rhude gear. Ralph Lauren had everybody fawning over its Milan runway show. Custom versions of the classic Timberland Field Boot have been a standout footwear trend.
We rounded up some of the biggest moments across style and streetwear, from viral celebrity looks to global trends, below. These are The Biggest Style Moments of 2026.
Make sure to bookmark this page and check in throughout the rest of 2026. It will be frequently updated.
When: Jan. 2, 2026
Trax NYC started off 2026 swinging. The now-viral video clip showed the veteran of New York City’s Diamond District confronting another jewelry company, AKAY, for scamming customers using his name. Trax later said that AKAY’s people attempted to kill him during the heated exchange. George and Freddy Akay would later be arrested and charged with assault. But the initial scuffle will live on forever in the internet hall of fame.
When: Ongoing
Timberland Field Boots have always been popular in the wintertime. However, they have always seemed overshadowed by their close cousin, the Six-Inch. This winter, the tides seemed to have shifted a bit. The Field Boot has some juice. It isn’t just the classic “Beef and Broccoli” colorway either. Collaborators like Starcow Paris have delivered some premium takes on the silhouette. Independent creators remixing the boot, from Dreamerz’s (previously known as Trapland) colorful pairs to Loso and Greedy Unit’s collabos to DarkPhilKnight’s wool versions have made the most noise. It’s too early to call it, but the Field Boot could end up being the biggest footwear trend of the year when 2026 is all said and done.
When: Jan. 13, 2026
The parent company of iconic luxury retailer Saks Fifth Avenue, Saks Global, filed for Chapter 11 bankruptcy on Jan. 13. This came after months of compounding debt and missed payments that impacted supply chain issues. Selfishly, we’re just looking forward to some of those steep discounts when they inevitably hit.
When: Jan. 13, 2026
Kai Cenat’s fit pic dumps on Instagram have been impressive for some time now. This year, he decided to take his love for fashion to another level. In January, he announced that he would be taking a step back from streaming to focus on developing his new clothing line, Vivet. While we still don’t know much about the venture and how much progress Cenat has made with the line, we do know he is keeping his ideas in a journal that he has been toting around. Most notably, we saw him out at Paris Fashion Week Men’s taking in shows from brands like 424 and Louis Vuitton. Cenat’s foray into fashion has been pretty polarizing. Personally, we can’t wait to see what he cooks up.
When: Ongoing
Behind the creative vision of former designer Greg Betty, Vans experienced a major resurgence in 2025. The biggest hits included the Chanel-inspired “Souvenir” and embellished pairs of the Old Skool. That momentum has continued in 2026 with another Chanel-inspired drop on the Authentic, and more pairs of embellished Old Skools in classic color schemes. We also can’t forget about the continued success of the Satoshi Nakamoto partnership. While it will be interesting to see how long Vans can make this very specific aesthetic resonate with its customers, they are definitely on a winning streak right now.
When: Jan. 16, 2026
Everyone wants to be Ralph. Countless brands have references the timeless Americana looks that Ralph Lauren perfected. Some have even done it very well. But at the end of the day, there is only one Ralph. In case anyone forgot, Ralph used its Milan Fashion Week to remind everyone why its the blueprint. The presentation started by showcasing expertly-styled Polo looks that featured bright rugby sweaters, leaf camo trousers, and classic Fair Isle knits. The more formal Purple Label line came next, which mixed pristine tailoring with pieces like fur overcoats. Top to bottom, it was one of the brand’s most impressive shows in years.
When: Jan. 19, 2026
No, this wasn’t another AI-generated image that popped up on your timeline. Pope Leo actually got blessed with some Rhude. During a visit to the Vatican, Rhude founder Rhuigi Villaseñor gifted him a brown varsity jacket. Villaseńor said it best when he spoke to GQ about the encounter, “I guess the drip is now holy.” The jacket will definitely look good with Pope Leo White Sox caps.
When: Jan. 20, 2026
As influential as streamers have become, we haven’t seen many high profile clothing brands align with them beyond sponsored content and brand deals. That’s why 424’s Fall/Winter 2026 seemed like an important moment in the streamer/fashion relationship. 424 founder Guillermo Andrade had streamers Jason the Ween and Brucedropemoff walk in the show. Kai Cenat watched from the front row. It was Andrade’s way of welcoming streamers to the table in a more official way than we have ever seen. It will be interesting to see how that relationship evolves moving forward.
When: Feb. 7, 2026
Bad Bunny’s Super Bowl LX halftime show was a spectacle worth celebrating. One of the more surprising wrinkles of the performance was who made the custom attire that he wore. It was Spanish fast fashion label Zara.
The monochromatic look featured a cropped football jersey featuring his family name “Ocasio” and number 64 layered over a collared shirt. On the bottom, a pair of classic chinos and his Adidas BadBo 1.0s on feet. The understated look allowed the powerful visuals and stage buildout, which were filled with references to Bad Bunny’s Puerto Rican heritage, to be the focus.
When: Feb. 15, 2026
As incredible as vintage NBA warmup jackets are to style off the court, the modern stuff usually isn’t held in the same regard. The 2026 All-Star Game warmups surprised us. The shade of blue made them almost look like they were made of denim. The giant logo on extending on the sleeve of the jacket was perfect. The font on the pants was clean. There’s a reason these swiftly sold out upon release. If you got one, consider yourself lucky. We think these may be a valuable vintage piece in a few decades.
When: Feb. 19, 2026
Ebay is trying to speak to the youth. In an effort to resonate more deeply with Gen Z, the online auction platform purchased secondhand clothing resell platform Depop for $1.2 billion. The deal is expected to officially close in the second quarter of 2026.
When: Feb. 6-22, 2026
U.S. figure skaters Alysa Liu and Ilia Malinin didn’t just capture America’s attention during the 2026 Winter Olympics through their skills on the ice. They also made headlines with their unique attire. For Liu, it was her striped halo hair, lip piercing, and homage to Bay Area legend Mac Dre as she posed with her gold medal. For the “Quad God” Malinin, it was his $1,300 Balmain jeans and NF merch that he wore to skate his one of his routines.
Both young skaters injected figure skating with some Gen Z influence on its biggest stage. It was a welcome switch from the usual classical music and leotards.
When: Feb. 23, 2026
The 2026 Met Gala is still a few months away, but its dress code is locked in: “Fashion Is Art.” There are so many interesting ways to interpret the theme. Thinking about all of the custom and archival pieces that the most stylish celebrities will arrive in this year makes this one of the most anticipated Met Gala carpets in recent memory.
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