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Apparently, it’s 2016 again.
As fun as it has been to see all of our close friends share their 10-year-old throwbacks, we were curious how some of our favorite celebrities have switched up their style.
Style icons like ASAP Rocky, Rihanna, and Kanye West have always been put together. Putting their styles from the past and present next to each other shows you exactly why. They have constantly evolved and experimented with different aesthetics.
Take a look at How Our Favorite Celebs Style Has Evolved From 2016 to 2026, below.
Ye was operating at the peak of his powers in 2016. There were literally hundreds of fit pics to choose from to represent that time period. The distressed denim. The Adidas Yeezys. The TLOP merch. If you cared about streetwear, chances are you were mimicking his outfits from that era. These days, Ye is much more lowkey and typically opts for all-black outfits from his label Yeezy. The influence is still there, but it doesn’t hold a candle to what he was putting on 10 years ago.
With the release of Purpose and help of Jerry Lorenzo, Justin Bieber shed his teeny bopper image in 2016. The distressed denim and ripped flannels channeled the grungey aesthetic of era’s past. Nowadays, you’d be hard-pressed to find him rocking a fit like this. Instead, he prefers super baggy pants and sweats from his own basics label SKYLRK.
In 2016, Timothee Chalamet was just a theater kid trying to break into Hollywood. Nowadays, he’s one of the most talked-about actors, thanks to his Golden Globe-winning performances in flicks like Marty Supreme, diehard New York Knicks fandom, and endless number of custom Chrome Hearts fits. Timmy Tim definitely wins our Most Improved Player award.
Capitalizing off of her King Kylie era from a few years prior, everything that Kylie Jenner wore became a trend for stylish young women around the world in 2016. Her hair changed colors and lengths frequently. Now, her personal style doesn’t shift nearly as drastically. Instead, the billionaire (who sticks to long brown hair) is usually spotted in dresses and other custom looks from some of the most prestigious designers in the world.
Rocky’s style has experienced one of the most jarring shifts. He’s traded in the skinny jeans and Gucci tees for perfectly tailored Dior suits. Despite the drastic transformation into his more timeless dad swag era, he’s maintained his spot as one of the best dressed rappers in the world.
In 2016, Carti was bubbling rapper using his new rapper money to acquire streetwear grails from Supreme and Undercover. Fast forward to 2026 and he’s influencing an entire generation of devoted fans to dress in Rick Owens, Chrome Hearts, Margiela, and backwards NBA throwbacks. What a difference 10 years makes.
Some Uzi fans still beg for them to bring back the purple dreads. The colorful hair and tight clothes helped usher a rockstar-inspired wardrobe into hip-hop that has persisted to this day. While some of the luxury bags and diamond accessories remain, Uzi’s style has leaned much more into the world of luxury fashion in the present day.
Rihanna has effortlessly shifted between chic luxury looks and streetwear for years. The main difference: back then she redefining what on-stage style looks like on her Anti tour and now she is inspiring to-be mothers everywhere to embrace their baby bumps without sacrificing their style. While the intention has changed, her status as the best dressed woman in the world has not.
A fresh fade, OVO varsity jacket, and Air Jordan PEs was the go-to uniform for Drizzy back in the day. While he still hasn’t cemented his place in “Best dressed rapper” conversations, custom Gruppo Vava gear, an endless supply of obscure vintage tees, and insane diamond chains by Alex Moss have elevated the rapper’s style to new heights.
Lil Yachty’s red braids and Nautica fits were defining visuals of the Soundcloud era. Throughout his career, he’s definitely leveled up. Boat has built a strong case as one of the best dressed rappers today, thanks to his effortless mix of high-ticket luxury pieces, emerging labels, and rare vintage gear.
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