Drew Barrymore's Best Menswear Inspired Looks

While incorporating menswear into your wardrobe can be intimidating, Drew Barrymore is one of many  fashion-forward celebrities demonstrating why you should raid your boyfriend's closet. From pinstripes and tweed to neckties and tailored trousers, the Hollywood figure has incorporated countless menswear staples into her wardrobe over the years. She has especially channeled a '70s- and '80s-infused take on tailoring since launching "The Drew Barrymore Show," incorporating earthy colors, retro patterns, and oversized silhouettes into her talk show host outfits and red carpet ensembles.

"I love tailoring," revealed Barrymore on her show, having worked with celebrity stylist Lee Harris for multiple decades. "I've been in costume houses my entire life and I have learned about tailoring and alteration from these seamstresses. It's just the greatest education I could have ever hoped for." With this passion in mind, it's no surprise that the "50 First Dates" actor has managed to effortlessly nail down the tailored trademark and gender-bending vibes of menswear.

Though Drew Barrymore was mostly serving indie sleaze back in the '90s, the "Never Been Kissed" star repped a menswear staple at the 1992 premiere of "Reservoir Dogs." She wore a classic black blazer with a pair of cuffed, denim shorts and accessorized with chunky black heels for a casual, effortlessly cool look. While this outfit, made distinctly '90s with thinly-groomed brows and a desaturated lip color, is a major departure from her modern look, it ranks as a standout for demonstrating just how many ways Barrymore can pull off menswear.

Next, Drew Barrymore infused menswear with sexy flair when she paired a sleek white suit with a peekaboo black bra moment at the premiere of "Charlie's Angels 2: Full Throttle." The actor posed with co-stars Lucy Liu and Cameron Diaz at the 2003 event, wearing her long blonde hair in messy waves and sporting a grungy eyeshadow look. "I loved seeing that strong triangle of women," Barrymore told InStyle about the trio's outfit choices, noting that they were inspired by Destiny's Child. "Letting everybody know that they were together, they were united, but they also dressed according to what made them feel good."

Drew Barrymore took her menswear into the 2010s by styling skinny-fit pants with a grungy graphic tee and sky-high heels. The navy trousers were worn with a matching blazer featuring satin-trimmed cuffs and black lapels, accessorized with a gold-toned necklace, a pink clutch, and a pale lip. The ensemble, which she wore to a Tommy Hilfiger opening in February 2013, feels very of-the-time and boss babe-inspired, but Barrymore managed to pull it off with her signature cool-girl charm.

When it comes to her talk show, Drew Barrymore has cultivated a very retro-inspired aesthetic that often features some of our favorite menswear fashion elements. A standout example of this comes from January 2021, with the former child star channeling light academia by pairing a beige midi skirt and matching vest with a puff-sleeve blouse in brown plaid. She accessorized with a polka-dotted tie, a silver watch, and heeled boots, wearing her brown hair in loose waves. The entire ensemble gives fashionable Oxford professor, with Barrymore expertly balancing suit staples like a vest and tie with more traditionally feminine fashion elements such as skirts and heels.

Drew Barrymore wore another striking look in November 2021, bringing major '70s vibes to her menswear with a brown and orange color scheme and retro floral print. She wore a flowy, rust-colored blouse with fitted cuffs, pairing the patterned piece with burgundy slacks and a brown vest from Ralph Lauren. The "Santa Clarita Diet" star accessorized with a simple brown belt and orange flower pin, rounding out the look with a softly-waved hairstyle and a dark lip color. We're obsessed with the vintage feel of this menswear-inspired 'fit, and Barrymore really knows how to rock this earthy color scheme.

Drew Barrymore's haberdashery-inspired ensembles aren't limited to her talk show, as she cut a fine figure at the 26th Annual Webby Awards in May 2016. The Hollywood star wore an all-white suit from Fendi, with the designer jacket showcasing a silky peak lapel while the tailored trousers boasted crisp front creases. The actor actually credits Zendaya, who's had a jaw-dropping style transformation, and stylist Law Roach with inspiring her more menswear-centric wardrobe, pointing to the monochromatic suit that the "Dune" actor wore at a 2022 "Euphoria" event as the fashion catalyst. "When I saw this look, I went to Lee Harris, who I've worked with for twenty years, and I said, 'Lee, I'm ready to change,'" Barrymore revealed to Roach on "The Drew Barrymore Show."

Another vintage-inspired Drew Barrymore look comes from the TCM Classic Film Festival in January 2025. The California native wore a burnt-orange pantsuit over a silky button-up with ruffled cuffs to the event, accessorizing with a checkered necktie tucked into her blouse and brown, platform heels. While the suede-like fabric and rusty color of the wool suit harken back to the groovy aesthetics of '70s sport coats, Barrymore balances her tailored pieces with silk and ruffles for a stylish, gender-bending effect.

Lastly, Drew Barrymore took her haberdashery fashion to the next level when attending the 50th anniversary special of "Saturday Night Live," experimenting with tuxedo fashion elements at the February 2025 event. She wore a partially-unbuttoned dress shirt with tailored trousers and a silky cumberbund, styling the tailored pieces with a chain necklace, black clutch, and tousled waves. The TV personality opted to ditch the traditional tuxedo jacket for a more playful and casually undone look. Though Barrymore has worn menswear throughout her career, time has really cemented her as a tailored fashion icon.