Drew Barrymore is quite the fashionista, so it was no doubt quite a struggle to pick out some of her key style moments from the past 20 years.

The actress chats to People StyleWatch for its new digital issue, looking back at some of the ensembles that have meant the most to her over the years.

Giving fans some advice, she says: “Don’t get stuck, do what works for you and your body, and make your own rules.

“Because at the end of the day, if you’re not comfortable, you’re distracted. And you want to feel free and empowered.”

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One of the dresses picked out was the matching Stella McCartney white pant suit and black bra worn to the 2003 “Charlie’s Angels 2: Full Throttle” Los Angeles premiere.

Cameron Diaz, Lucy Liu & Drew Barrymore during Premiere of “Charlie’s Angels: Full Throttle” at Grauman’s Chinese Theatre in Hollywood, California, United States.
Cameron Diaz, Lucy Liu & Drew Barrymore during Premiere of “Charlie’s Angels: Full Throttle” at Grauman’s Chinese Theatre in Hollywood, California, United States. — Chris Weeks/FilmMagic/Getty

Barrymore recalls of posing in white with her co-stars Cameron Diaz and Lucy Liu, “We were really inspired by Destiny’s Child. They were taking colours and fabrics and styles, but they were making them very different for each of them and their body types.

“To me, that goes back to my love of tailoring, and it is not ‘one size fits all’. I love seeing that strong triangle of women who were out there dressing alike, letting everybody know that they were together, they were united, but they also dressed according to what made them feel good.

“We pulled up in a white vintage El Camino car with an orange interior. It was the car my character drove in the first movie. It just felt like, ‘We’re here to play.’”

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Barrymore also discusses the Andrew Gn backless white gown she wore to the 2009 “Grey Gardens” Hollywood premiere.

Drew Barrymore arrives at the Los Angeles Premiere “Grey Gardens” at the Grauman’s Chinese Theater on April 16, 2009 in Hollywood, California. (Photo by Jon Kopaloff/FilmMagic/Getty)
Drew Barrymore arrives at the Los Angeles Premiere “Grey Gardens” at the Grauman’s Chinese Theater on April 16, 2009 in Hollywood, California. (Photo by Jon Kopaloff/FilmMagic/Getty)

Calling it one of her “favourite looks,” the “Drew Barrymore Show” host remembers, “I was inspired by all the ’60s pinup girls, and we just went real big on the hair — couldn’t have more extensions in there.

“You could build a city inside that head. And I’d always wanted to wear a bib dress. A statement bib, you can’t go wrong. It’s so delightful. This is one of my favourite looks I’ve ever gotten to wear, and it’s a full character.”

Barrymore then talks about the Kate Spade dress she donned for a 2013 “Tonight Show with Jay Leno” appearance, insisting she was pregnant at the time but no one knew.

“THE TONIGHT SHOW WITH JAY LENO” — Episode 4544 — Pictured: Drew Barrymore arrives on October 7, 2013 — (Photo by: Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images)
“THE TONIGHT SHOW WITH JAY LENO” — Episode 4544 — Pictured: Drew Barrymore arrives on October 7, 2013 — (Photo by: Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images)

He shares, “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.

“Women are so stressed out. They just want to get to the safe mark. They want it to be their news. I didn’t get the chance to tell any friends, but I’m not angry or bitter. I thought it was hilarious that I would be such an idiot to just walk out waving the sonogram. It was my new white flag to surrender into my new life. And you know what? In a weird, sick way, it’s like, ‘Oh, pressure’s off. News is out. Move on,’” she adds of being spotted with the photo.