Drew Barrymore Looks Back at 20 Years of Her Style

When we decided to relaunchPeople StyleWatchas a digital issue, there was one thing everyone knew: It needed a dose of Drew! Luckily, the actress, style icon and four-timePeople StyleWatchcover star was just as excited about the opportunity to collaborate with us.

“Accessibility and affordability is everything to me. When I get to wear these elaborate, expensive outfits — and that could be everything from a suit to a big dress — they all go back the next day. I don’t get to keep any of it,” Barrymore tellsStyleWatchon the set of her daily talk show,The Drew Barrymore Show. “I too am trying to learn from the best of what’s out there and figure out how I can put it into my own closet. I don’t shop designer or expensive, but I do get turned on to everything that’s happening in fashion, and then I want to bring that back into real life.”

The entrepreneur, 47, says her love for fashion dates back to her childhood on film sets, where she would learn from the costume pros about what it takes to make clothes look great.

Her best advice is to find silhouettes and styles that feel authentic to you, regardless of trends.

“Don’t get stuck, do what works for you and your body, and make your own rules,” she says. “Because at the end of the day, if you’re not comfortable, you’re distracted. And you want to feel free and empowered.”

Barrymore is not just aStyleWatchcover fave, but she’s also a mainstay in the pages of the weekly magazine, and shares that it’s as special for her as it is for us.

“Peoplemagazine is my safe space. That’s where I’ve been doing covers since I was seven years old, and it’s where I’ve celebrated every milestone of my life,” she shares. “I don’t even know how many covers cumulatively I’ve been lucky enough to be on. Launching the [talk] show in the magazine felt really good, because it was a really important, hopeful chapter for us. Every time I want to do something important in my life, I go straight toPeople.”

Watch the clip above for Barrymore’s look back at 20 years of show-stopping looks, and catch a few of our favorite highlights below.

2003Charlie’s Angels 2: Full ThrottleL.A. Premiere in Stella McCartney

2003 Charlie’s Angels 2: Full Throttle L.A. Premiere in Stella McCartney.Kevin Winter/Getty

Kevin Winter/Getty

2005 Oscars in Atelier Versace

BEI/Shutterstock

“I think I really wanted to wear a serious dress. I wanted serious hair. I wanted an updo. I always had mood boards. This night I was trying to channel more Elizabeth Taylor, more Eva Gabor. I usually went for a more bedroom-y, sexy character a lot on the red carpet. But for some reason this time I was like, ‘I would like to be a ’50s classic woman.’

Sometimes I feel like my hair is all over the place, and I’m not wearing makeup and I’m in my sweatpants. And sometimes you just see those women who look so showered and clean and put together and accessorized and their hair’s in an updo. And maybe there was some teasing and back combing going on, and you’re like, ‘I should try that one day.’ This was the day I tried that, and I didn’t do it very often after that. But I’m glad I did it in this moment.”

2009Grey GardensHollywood Premiere in Andrew Gn

Jeffrey Mayer/WireImage

2010 Golden Globes in Atelier Versace

“Lee Harris, the stylist I’ve worked with for over 20 years and work with every single day of my life, he had this made for me, and I’m forever indebted. I remember when they talked about these sea anemone adornments and how that was going to work. They also made this sick corset underneath that you can see is all laced up in the back. It gave this beautiful boning. It was the kind of dress where I just thought: hair and makeup really take a backseat. Let the dress do its thing. Go clean. Go classic. Don’t fight it. This needs no enhancement.' ”

2013The Tonight Show with Jay Lenoin Kate Spade

Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty

“I knew that I was pregnant with my second daughter, Frankie, and nobody else knew. So I needed to find something that fit, and it made me comfortable. But this outfit means so much to me because it is the first outfit I wore out in public knowing I was pregnant with my second daughter, but was keeping the news a little quiet.

My first ‘outing’ of being pregnant was because I walked out of the doctor’s office with the sonogram in my hand, and there was a paparazzi in the parking lot. I tried to do it differently the second time after that information came out.

2014 Golden Globes in Monique Lhuillier

Steve Granitz/WireImage

“This dress is so special to me. It’s Monique Lhuillier and, boy, does she know how to dress women. This one is a fairytale but very playful and whimsical to me. And I’m very pregnant with Frankie. I’m about six, seven months, and I had never felt better in my life. I just love this dress so much. She gave me so much joy, so much happiness.

Sometimes when you’re pregnant, you’re feeling your best. You feel like this energized gazelle. You go through grueling, crypt-keeper morning sickness for the first several months.Then you go through, like, ‘I’m unstoppable. I’ve never had this kind of energy.’ And then you go through, like, ‘Get it out!’

And she sent me right out on a big red carpet when I could have been feeling like, “Oh, I’m uncomfortable in my body.” And instead, I just did not want to take the dress off. I didn’t want to leave. I went for pizza right afterwards. Another benefit of being pregnant: You don’t have to play that whole red carpet BS game of, ‘I’ve got to look great in this dress.’ I was like, ‘I look great, and I am eating pizza!’ ”

2021 CFDA Awards in Christian Siriano

Presley Ann/Getty

“I hadn’t left the house, I hadn’t traveled, [because] I never wanted to shut the show down for COVID. I took this so seriously, and I felt like it was really my responsibility to keep myself safe. This was kind of my first night back out. It had been about two years since I had gone to any event. And it was Christian Siriano who got me to come out. When he sent this dress, I was like, ‘Oh, hell yes, I’m going!’ I love this dress so much. He has it in his archives. I dream about it. Every time I see it, it puts a smile on my face, and it’s my favorite color — an electric yellow.”

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source: people.com