Chelsea Handler’s Transformation is Turning Heads

At 19, Chelsea Handler moved from her hometown of Livingston, New Jersey, to Los Angeles, California, to pursue a career in acting. “I moved out to LA when I was about nineteen to become a famous actress,” she said in 2005 (via Pop Entertainment). However, getting cast wasn’t as easy as she thought. “I realized that there was a lot more competition than I had bargained for. You know, with the perfect girls. There were girls that were prettier and skinnier and all — the whole thing,” Handler explained. “I was like, well, shoot; I better do something other than try and become an actress. I wanted to do something to kind of set myself apart from everybody.” And just like that, Handler switched career paths, at least for some time. “I figured I’ve always had a big mouth, so stand-up would be a good idea, although I was petrified. It’s not an easy thing to get up in front of complete strangers and just try to be funny,” she added.

In the early 2000s, Handler made her breakthrough thanks to shows like “Girls Behaving Badly” and her role as a correspondent on “The Tonight Show.” Now in her mid-20s, Handler was ready to make a name for herself in the industry as a stunning blond comedian whose wit and timing matched — and surpassed — some of the most famous male comedians of the time. Handler’s style was classic early aughts — think halter tops, bright colors, and statement jewelry. Since then, Y2K fashion has had its comeback, but the original era will forever remain the most iconic interpretation of quirky and bold fashion.

The year 2006 was a major one for Chelsea Handler’s career, as the comedian started hosting “The Chelsea Handler Show” on E!. She quickly became known as one of the funniest women in the industry, but Handler admitted that she knew her humor wasn’t for everyone. ”I guess I’m an acquired taste. Some people love me and some people hate me, and that’s fine because comedy is so subjective,” the star said that year (via Cape Cod Times). ”My comedy is observational, if you have to label it. Some of the things I talk about happened to me and some of them happened to friends… And some of it is born out of just how ridiculous life can be, whether you’re single and dating or someone who gets married and overnight it turns into a nightmare.” While it hasn’t always been everyone’s cup of tea, Handler’s comedy has particularly resonated with women who felt like the field of comedy needed more female voices. 

As she was becoming a more well-known name in Hollywood, Handler’s style became even louder and more colorful. Dresses in bold patterns and neon clothing became a staple for the star’s red carpet attire, and even though a tailored orange blazer might not be considered red carpet fashion today, the look somehow worked well at the time.

As the 2000s approached their end, Chelsea Handler was a well-known name in the world of stand-up comedy. “I wanted to say my own stuff. I wanted to talk. And I realised that stand-up was the perfect way to do it,” Handler told The Telegraph in 2009. “So I had to do that. I’ve always been a loudmouth.” Handler also never gave up on acting, appearing in numerous shows over the years. 

Speaking about being a woman in a male-dominated field, Handler admitted that she thought of it as an advantage at the time. “I think it’s easier because there aren’t so many women. There is not as much competition,” she told The Telegraph. “Being a stand-up comedian is not a career that women are drawn to. You’re on the road and touring and living in disgusting hotel rooms, which is what you have to do at the beginning. You have to work your ass off… It’s really hard to do, but once you get good at it, it’s totally worth it,” she added.

Now in her early 30s, Handler’s style drifted away from the loud and colorful aesthetic of the early aughts as she began embracing a more sophisticated and classic look. Of course, that by no means meant that her style had become boring — if anything, her black red carpet dresses made her look edgier and cooler.

By the time the 2010s kicked off, Chelsea Handler was slowly becoming the queen of knee-length dresses on the red carpet. Still, the comedian used every opportunity to showcase just how versatile her style was becoming, and every style of dress that she rocked truly did suit her. 

While comedy remained at the forefront of her career, Handler revealed that she had plans to venture out and explore other spheres of being a public persona. “I feel like there’s only so long I can go around talking about Lindsay Lohan and Tiger Woods,” the star told Forbes in 2010. “There are a lot of issues I’m really interested in — government, politics — that I’d like to explore. Comedy is still the most important thing, but I definitely think I’ll move on to something else after this.” Here, she further cemented herself as a force to be reckoned with, and that directly influenced the confidence she’d been building in her fashion and beauty aesthetic.

Chelsea Handler’s love life has been in the spotlight over the years, too. In the early 2010s, she briefly dated rapper 50 Cent, after which she started a relationship with businessman and hotel manager André Balazs. “My boyfriend and I, we’ve broken up a couple of times, we’ve gotten back together and we’re trying to figure out how to live a life together,” Handler told E! News in 2013, opening up about the difficulties of a long-distance relationship. “[André is] all over the world, I have to be in L.A. for my show for a certain amount of time and he’s opening up hotels everywhere… But when you really want to be with someone, you can make that work.” Being there for a loved one when you’re long-distance isn’t easy, and by the end of the year, the two had parted ways. 

While Handler’s style had toned down and become much more minimalist as the 2010s kicked off, in 2012 and 2013, the star embraced a fail-proof combination for industry events: skinny black pants with a chic, loose blouse. Handler spiced up the aesthetic with beautiful and fashionable accessories but never took it overboard. Seemingly, the colorful and bold era of Handler’s fashion was over.

By the mid-2010s, Chelsea Handler was known for her work as an actor and producer, with projects like “This Means War” and “Fun Size” under her belt. While her career was thriving, it seemed as if Handler’s personal life sadly wasn’t. “I’m just like, the person that’s not getting married so I like it and I think it’s a good example to not have that be part of your identity,” the star said in a 2014 interview with Gwyneth Paltrow (via HuffPost). “The truth of the matter is, I don’t really know how to balance a relationship and my life. I’ve never been able to really do that.” 

However, just because she didn’t see marriage in her near future didn’t mean that Handler was giving up on love. “I love men. I have men around all the time, I’m not an idiot, but you have to have somebody that brings out the best in you and I’ve never met somebody that really brings out the best in me,” the comedian added. “And I want to bring out the best in them. You don’t want it to be a one-way street.”

As Handler entered her 40s, she was clearly finding more and more confidence in who she was and what she wanted. And we don’t mean that only when it comes to her love life — Handler was increasingly confident in her fashion choices as well, and it showed. Black clothing became a staple for the star, who always kept her outfits interesting by incorporating different textures and details.

The more established Chelsea Handler became, the more vocal she was about things that matter. For example, she has repeatedlyemphasized the importance of women supporting one another. “We have to get better at being there for each other,” Handler told Harper’s Bazaar in 2017. “You don’t have to be best friends with women you don’t like, but you do have to be a sister to them.” She also explained that fighting for those who don’t have a voice is important to her. “You have to stick your neck out for every group that’s being marginalized right now,” Handler said. “You have to really dive deep and to try to understand people who aren’t like you, who haven’t had the same life experience that you have had: every refugee, every immigrant, every single working mother, everyone who doesn’t have access to health care, every single person who’s unemployed and struggles.”

In 2016 and 2017, Handler gave herself permission to explore fashion again, often rocking bohemian and detailed looks. From intricate patterns to dramatic silhouettes, the star seemed as confident as ever in herself and what she likes. For the Glamour Women of the Year even in 2016, she went with a long-sleeved midi dress that was hard to pull off due to its busy pattern, but the star knew that combining it with simple heels and a braided updo would allow the dress to take center stage. With this outfit, Handler was clearly saying goodbye to less-is-more fashion with maximalist outfits. The comedian also revealed that she was her own priority now. “I am always doing nice things for myself. I like to remind myself I’m on my side,” she told Marie Claire at the time.

In 2019, Chelsea Handler published her memoir, “Life Will Be the Death of Me: … and You Too!” and noted that writing it was very cathartic. The star said it was about her experience with therapy after President Donald Trump’s election in 2016. “It’s a lot about the grief I had not visited about my childhood, that I thought I could get through my life without having to deal with,” she said (via The Arizona Republic). “And it’s about that kind of thing sneaking up on me after the election and finally feeling like, for the first time, I had to sit down and talk to somebody.” 

The comedian added that writing the book was extremely helpful, and sharing it felt important. “It felt great and it felt like it just kind of vomited out of me. I was learning things in therapy that were opening doorways and hallways and everything was connected,” she said. “You make all these leaps about why you behave a certain way or why you get so angry at certain circumstances. And I just knew I had to share it.”

As the 2010s drew to a close, Handler’s transformation was noticeable in her choice of clothing. Gone were the days when the star only embraced black clothing and a minimalist look. Now, the comedian was confident enough to explore bold fashion again in a way that went back to her fun and colorful roots. From a sparkly silver jumpsuit to a red and metallic dress, Handler was undeniably having a lot more fun with her image, daring herself to think outside of the box when it came to fashion.

The COVID-19 pandemic arrived in 2020, and with that, the entertainment industry was put on hold. Just like most of us, Chelsea Handler was stuck at home, doing nothing. “For the first two weeks of COVID, I treated it like it was Spring Break. I went off. I ate what I wanted. I took as many edibles as I wanted. I had martinis in the middle of the afternoon,” she told Interview in 2020, revealing that after two weeks of relaxing, she decided to focus on her health and fitness. “I’ve definitely been getting more sleep than I’ve gotten in the last five years. I think that’s what’s rejuvenating me. With physical fitness, I have to say, it’s so important to be physically fit because it helps you be mentally fit, too.” Like many of us, this wasn’t always a priority for her. “That’s something I didn’t appreciate when I was younger. I always thought working out was such a pain in the a**,” she added.

As the industry slowly began opening up and red carpet events returned, the comedian stunned in looks that left our jaws on the floor. For the 2021 People’s Choice Awards, the star went with a black-and-white gown that was incredibly simple, yet the star looked absolutely stunning in it. With minimal accessories and subtle waves in her hair, Handler proved that the second half of your 40s can be incredibly empowering. While there are some outdated items that women over 40 should avoid wearing, this dress definitely isn’t one of them.

Chelsea Handler has been very open about her personal life over the years, and in 2023, the star explained why she chose not to have children. “I’m very outspoken about not wanting to be a parent because I don’t think I have the skills,” the comedian said on “The Tonight Show Starring Jimmy Fallon.” She added, “I’m not equipped with what it takes to answer all of those questions to children because they don’t just ask you once… I have enough nieces and nephews to know that I don’t have the tolerance for that kind of line of questioning about things that I really don’t even know the answers to.” Her openness about remaining child-free is refreshing, as not many in the entertainment industry openly discuss this choice.

For the 2023 Critics’ Choice Awards, Handler stunned in a breathtaking orange one-shoulder gown. The unexpected color suited the star perfectly, but it was her voluminous hair with a deep side part that stole the show. This hairstyle was perfectly trendy, as 2023 was the year that the side part came back, and we showed you how to rock the Y2K-inspired hair trend. “I wanted Chelsea’s red-carpet look to be a voluminous, sexy blonde bombshell style,” celebrity hairstylist Adir Abergel told New Beauty that year. Needless to say, the hair magician effortlessly executed the look.

Chelsea Handler turned 50 in 2025, and it was clear that she was just entering the best decade of her life. The star looked stunning, but it was her confidence that really radiated beauty. For example, she did a phenomenal job hosting the 2025 Critics Choice Awards, which helped distract from the worst-dressed celebrities that bogged down the red carpet. 

Handler was also adamant about taking care of herself, both physically and mentally. In a conversation with Page Six, the comedian said that skincare plays a major role in her daily routine. “Moisturize, moisturize, moisturize,” Handler said. “I moisturize all parts of my body, and it pays off. I have very, very soft skin,” she said, adding, “It’s always important to protect your skin from wind and sun. Those are the most important things.”

While it isn’t uncommon for women to fear aging, Handler has shown just how graceful and natural it is. “I don’t care about age — I honestly don’t even think about it in that way,” she told New Beauty in 2025. “I think about it in the terms of what’s happening in my life. What’s my level of happiness? What’s my level of presence?” And frankly, her 50s are only opening up new doors for the comedian, actor, writer, and producer, so we can’t wait to see what the future holds for her. Now, for another celebrity deep dive, check out the complete transformation of Hunter Schafer.