When I was working on my successful celebrity rebrands list, I noticed something I couldn't unsee: their style had evolved just as dramatically as their careers. And that got me thinking about celebrity stylists and some of the wildest fashion evolutions we've watched happen over the years. Because I have to say, some of these transformations have been so good that we may have collectively forgotten what these celebs looked like before their stylists got involved.
And before you come at me with, “Well, they were kids back then,” fair point! But some of these celebs have been working with stylists for years, and the glow-ups have been VERY real.
Here are 24 celebrities whose style evolutions might make you do a double take.
THEN: When Dua first broke through, her wardrobe leaned heavily into the typical late-2010s pop-star formula: crop tops, bodycon dresses and LOTS of leather.
NOW: After meeting Lorenzo Posocco on an Italian magazine shoot in London in 2015, Dua Lipa found the person who would help shape her fashion evolution. Since then, he's helped her build a style that's equal parts sexy and playful and screams her, like the custom Jean Paul Gaultier pieces and those signature Paris Texas boots.
Here’s Lipa, side by side, then and now:
THEN: From 2013 to 2016, Hadid was still finding her style, bouncing between jeans and tees, girly sundresses, and plenty of athleisure.
NOW: Then Mimi Cuttrell came along, and Gigi's style took a completely different direction. Her laid-back California look was replaced with outfits that were much edgier, sometimes slightly oversized, and (much) more high-fashion.
Here’s Gigi, side by side, then and now:
THEN: Early One Direction Harry was mostly in skinny jeans, basic tees, boots, and conventional suits.
NOW: Harry's current wardrobe is a far cry from his early One Direction days. Since teaming up with Harry Lambert in 2014, he's leaned into everything from pearls and flared trousers to sheer tops and sequins, while his Celine, Prada, and JW Anderson tour looks and memorable Met Gala outfits have helped make his fashion just as (if not more) recognizable as his music.
Here’s Harry, side by side, then and now:
THEN: When Zendaya went to her first movie premiere at just 14, she put the whole outfit together herself with pieces she'd picked up at Target. She felt completely confident in it, too, saying she felt “fly.” Then, in 2011, she teamed up with Law Roach, and that's when the fashion experimentation really started to take off.
NOW: These days, if there's one celebrity who always seems to be dressed to the T for an event, it's Zendaya. With Law Roach by her side—the first-ever recipient of the CFDA Stylist Award and a 2019 InStyle Stylist of the Year winner—she has become known for carefully planned looks that often tie into whatever she's promoting.
Here’s Zendaya, side by side, then and now:
5.
Pedro Pascal - Jamie Mizrahi
THEN: Pedro's earlier red-carpet wardrobe was mostly classic suits that didn't draw much attention.
NOW: Pedro's style really took off in 2023, when stylist Julie Ragolia helped turn him into an unlikely menswear crush and a full-blown fashion favorite. His unexpected choices quickly became part of his image. In 2025, he began working with Jamie Mizrahi, who now handles his red-carpet and press tour looks for projects including The Fantastic Four: First Steps and Eddington.
Here’s Pedro, side by side, then and now:
6.
Emma Stone - Petra Flannery
THEN: Early in her career, Emma's red-carpet style was cute and feminine, but she often played it pretty safe with colorful dresses and classic silhouettes.
NOW: Emma began working with celebrity stylist Petra Flannery in 2007, around the time of her breakout role in Superbad, and the two have continued working together ever since. Flannery was even ranked No. 1 on The Hollywood Reporter's 2015 list of the 25 Most Powerful Stylists and won Stylist of the Year at the 2017 InStyle Awards.
Here’s Stone, side by side, then and now:
7.
Bad Bunny - Storm Pablo and Marvin Douglas Linares
THEN: Early Bad Bunny was mostly tracksuits, casual streetwear, and relaxed everyday looks. He wasn't completely predictable, though—every so often, he'd show up in a suit, like the purple one that became one of his more memorable early looks.
NOW: Thankfully, Bad Bunny's style is a whole different story now. Since around 2019 or 2020, stylists Storm Pablo and Marvin Douglas Linares have been behind many of his biggest looks, from the "Yo Perreo Sola" skirt to his silver 2020 Super Bowl outfit.
Here’s Bad Bunny, side by side, then and now:
8.
Lewis Hamilton's - Eric McNeal
THEN: Early on, Lewis Hamilton mostly dressed like, well, a professional athlete. His wardrobe leaned heavily on sportswear and Formula 1 gear, with not much of the fashion experimentation we see from him now.
NOW: Lewis started working with Law Roach around 2021, and by 2022, stylist Eric McNeal had taken over. Since then, Lewis has made the F1 paddock his own little fashion show, showing up in everything from high fashion tailoring to full-on runway looks and couture.
Here’s Hamilton, side by side, then and now:
9.
Beanie Feldstein - Erin Walsh
Beanie was already having fun with fashion before bringing a stylist on board. She styled herself for the red carpet, even rewearing her old prom dress to the 2018 SAG Awards and I kind of love that for her.
NOW: Then Beanie called up stylist Erin Walsh before the Booksmart premiere in 2019, and clearly decided to stick with her. Since then, her red-carpet wardrobe has gotten a lot more colorful and playful, with feminine dresses and fun designer pieces from the likes of Oscar de la Renta and Miu Miu.
Here’s Beanie, side by side, then and now:
10.
Paris Hilton - Sammy K
THEN: Back in her The Simple Life days, Paris didn't have a stylist telling her what to wear. From 2003 to 2007, she and Nicole Richie pretty much wore whatever they wanted on the show, which gave Paris the very early-2000s style she's now so closely associated with.
NOW: Paris still has a very specific idea of what she likes, but these days she has a stylist in her corner. After Kim Kardashian briefly helped her with her wardrobe back, Paris eventually began working with Sammy K, who has been behind some of her recent red-carpet and event looks since at least 2024.
Here’s Paris, side by side, then and now:
11.
Margot Robbie - Andrew Mukamal
THEN: Before the big red-carpet moments, Margot's style was pretty simple. Growing up on an Australian farm, she was used to throwing on shorts, T-shirts, and Converse, and she carried that same easygoing, girl-next-door vibe into her early acting days.
NOW: Margot's red-carpet style got a serious makeover once Kate Young came into the picture around 2016. They worked together through Margot's Chanel ambassador era. She later teamed up with Andrew Mukamal, who took things to another level during the Barbie press tour with all those carefully planned, Barbie-inspired looks.
Here’s Margot, side by side, then and now:
12.
Colman Domingo - Wayman Bannerman and Micah McDonald
THEN: Colman Domingo was never exactly clueless when it came to clothes. He had a thing for '70s soul stars, took cues from the stylish men in his family, and loved a good thrift find. Before getting a stylist (or two), his red-carpet looks mostly consisted of suits and clean-cut tailoring.
NOW: Colman's red-carpet wardrobe is a lot more interesting these days, thanks in part to his longtime stylists, Wayman Bannerman and Micah McDonald. The duo, who won Stylist of the Year at the 2022 Hollywood Beauty Awards and Men's Stylist of the Year at the 2025 Daily Front Row Fashion Los Angeles Awards, have helped him move away from the usual suit-and-tie look and embrace pussy-bow shirts, custom couture, and the dandy-inspired outfits he's now known for
Here’s Colman, side by side, then and now:
13.
Anne Hathaway - Erin Walsh
THEN: In the early 2000s, Anne's style was pretty safe. She mostly stuck to low-rise jeans, simple knits, and classic gowns that felt more 'Hollywood actress' than 'fashion girl'. She began working with celebrity stylist Rachel Zoe around 2004, and the two continued working together for about a decade before amicably parting ways in January 2014.
NOW: Anne's style didn't stop evolving after Rachel Zoe. She worked with Penny Lovell in 2014, which included her memorable gold Ralph Lauren gown at the 2015 Met Gala. Then came Law Roach in 2018, who pushed her looks even further. She now works with Erin Walsh, and her red-carpet looks continue to be a far cry from the safe, predictable gowns she wore early in her career.
Here’s Anne, side by side, then and now:
14.
A$AP Rocky - Matthew Henson
THEN: Before the stylists came into the picture, A$AP Rocky's style was very much a product of the scene he came up in. He mixed Harlem streetwear with skinny black jeans and Hedi Slimane-era Dior, giving his early looks a very specific underground-fashion feel.
NOW: A$AP Rocky has come a long way from the skinny jeans and streetwear he was known for early on. He met stylist Matthew Henson while shooting a Complex cover in 2012, and they've been working together ever since. Henson helped him bring his Harlem style into the world of high fashion, with Rocky now regularly mixing streetwear with pieces from Dior, Calvin Klein, and Gucci.
Here’s Rocky, side by side, then and now:
15.
Florence Pugh - Rebecca Corbin-Murray
THEN: Florence Pugh's red-carpet looks were VERY straightforward back then. It's almost as if someone had locked away the bold, statement-making side of her style—at least for a little while.
NOW: Then Rebecca Corbin-Murray came along, and it was like someone finally let Florence's fun side out. She's been behind some of Florence's biggest looks, including her first Oscars appearance in 2020, and the two clearly aren't afraid to have fun with fashion. Murray told Vogue, "She [Pugh] loves to be unexpected and has a playful, joie de vivre attitude when it comes to choosing looks."
Here’s Pugh, side by side, then and now:
16.
Sydney Sweeney - Molly Dickson
THEN: If you go back to Sydney's earlier red-carpet appearances, you'll notice just how different her fashion game was. Pretty dresses and simple silhouettes were more her speed back then, before she started leaning into the vintage glamour and bombshell looks that became her signature.
NOW: Molly Dickson has been behind Sydney's style for years, and you can definitely see the difference. Together, they've leaned into everything from Miu Miu and Christian Cowan to custom archival pieces, giving Sydney the glamorous, vintage-inspired looks that play a big part in carrying her image just as much as her acting.
Here’s Sweeney, side by side, then and now:
17.
Michael B. Jordan - Jason Bolden
THEN: Early Michael B. Jordan had the right clothes, but not always the right fit. His jackets and trousers were often a little too boxy, which took away from his athletic build instead of making the most of it.
NOW: Things changed pretty quickly once Michael started working with stylists. Jeff K. Kim helped him sharpen things up during his Creed era, playing with slimmer suits and patterns. These days, Jason Bolden is behind his biggest red-carpet moments, and the difference is pretty hard to miss because his suits actually work with his build now, instead of swallowing him up.
Here’s Michael, side by side, then and now:
18.
Hailey Bieber - Dani Michelle
THEN: If you lined up Hailey Bieber's early looks next to Gigi Hadid's, you'd probably have a hard time telling them apart. Back then, Hailey was also all about tight-fitting clothes, distressed denim cutoffs, stiletto boots, and those model-off-duty outfits that were everywhere in the mid-2010s.
NOW: Then Hailey started working with Maeve Reilly, and her wardrobe slowly began moving away from those super-tight, model-off-duty looks. Reilly helped shape her early red-carpet and street style before Hailey eventually teamed up with Dani Michelle, who has leaned into the minimalist, '90s-inspired looks we now associate with her.
Here’s Hailey, side by side, then and now:
19.
Lupita Nyong'o - Micaela Erlanger
THEN: Before working with her longtime stylist, Lupita Nyong'o's style was much more restrained. She even had a list of things she swore she'd never wear—including frills, peplum, velvet, and bias-cut pieces—so her early looks played it much safer than the fashion risks she'd eventually embrace.
NOW: Then Lupita met Micaela Erlanger in 2013, after Michelle Dockery introduced the two while Lupita was gearing up for the 12 Years a Slave press tour. And clearly, they clicked—Erlanger has been by her side ever since.
Here’s Lupita, side by side, then and now:
20.
Cillian Murphy - Rose Forde
THEN: Cillian Murphy's early style was about as understated as it gets. He mostly stuck to simple clothes that were comfortable and practical, with none of the flashy designer pieces or attention-grabbing looks you'd expect from a major red-carpet star.
NOW: Then Rose Forde came along, and Cillian's red-carpet wardrobe got a serious (yup, very serious) upgrade. She worked with him throughout the Oppenheimer press tour and awards season, including the custom archive-inspired Versace tuxedo he wore to the 2024 Oscars, where he won his first Academy Award.
Here’s Cillian, side by side, then and now:
21.
Addison Rae - Dara Allen
THEN: Back when Addison was first blowing up on TikTok, her wardrobe was basically a snapshot of peak TikTok fashion. Crop tops, loungewear and casual denim made up most of her looks before she started experimenting with a much more fashion-forward wardrobe.
NOW: Then came 2021, when Addison's fashion game really started changing as she stepped into her music era. She worked with Law Roach for some of her biggest early fashion moments, including the MTV Movie Awards and her first Met Gala. These days, she's working with stylist Dara Allen, who has helped take her love of Y2K fashion even further.
Here’s Addison, side by side, then and now:
22.
Jacob Elordi - Wendi Ferreira and Nicole DeJulio
THEN: Back in his The Kissing Booth and early Euphoria days, Jacob didn't exactly have the fashion game he has now. He mostly stuck to casual streetwear and standard young-Hollywood looks, giving him that very recognizable teen-heartthrob style of the time.
NOW: Then Wendi Ferreira and Nicole DeJulio came into the picture as Jacob's profile really started taking off. They've been behind some of his biggest red-carpet and public looks, especially during his Saltburn and Priscilla era, helping him nail that polished, cool style of a man we all suspected would make a pretty great James Bond.
Here’s Elordi, side by side, then and now:
23.
Ariana Grande - Law Roach
THEN: During her Victorious days, Ariana's style was very much giving teenage Nickelodeon star. She was all about floral prints and of course, that bright red hair. She also started working with her first official stylist, Brigitte Pilla, around this time, who went on to style her for her debut album, Yours Truly.
NOW: Then Law Roach came into the picture and helped turn Ariana's signature look into a full-on fashion era that had girls copying her left, right, and center, from the oversized hoodies and thigh-high boots to the famous high ponytail. She later worked with Mimi Cuttrell on major red carpets and campaigns, and Law has since returned to style her for the Wicked press tour.
Here’s Ariana, side by side, then and now:
24.
Timothée Chalamet - Taylor McNeil
THEN: When Timothée was first becoming a red-carpet regular, he was picking out his own looks rather than working with a stylist. He leaned into slim tailoring, dressed things down with streetwear, and seemed pretty happy figuring out his style as he went.
NOW: Timothée kept doing his own thing for a while, even as the red carpets got bigger. He eventually started working with Erin Walsh and Ryan Hastings around 2021, but these days, Taylor McNeill is behind his biggest looks, including his A Complete Unknown and Marty Supreme press tours. And I think we can all agree the man has figured out what works for him.
Here’s Timothy, side by side, then and now:
Which of these celebrity fashion evolutions was your favorite? And if your pick didn't make the list, tell me who you think deserves a spot in the comments!
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