Drew Barrymore has been famous since she was basically a toddler. Most of us remember her as the wide-eyed Gertie in E.T., but by the time the 1990s hit, that childhood innocence was long gone, replaced by a rebellious, floral-power aesthetic that defined an entire generation of photography. When people search for sexy pictures of Drew Barrymore, they aren't usually looking for modern gloss. They are hunting for that specific, raw 90s energy that only she could pull off—daisies in her hair, dark lipstick, and a "don't care" attitude that felt authentic because it was.
Honestly, her transition from child star to "wild child" was messy. It was public. It was also undeniably cinematic.
The Guess Campaign: 1993’s Defining Moment
If you want to understand why Drew’s image is so enduring, you have to look at the 1993 Guess campaign. Shot by Wayne Maser, these photos are legendary. At just 18 years old, she wasn't just a model; she was a mood.
She had just undergone a breast reduction a year prior, a move she’s spoken about candidly as a way to feel more comfortable in her own skin. In these black-and-white shots, she looks like a vintage pin-up girl who just happens to be wearing denim and lace. There’s a specific photo of her in a polka-dot top with a rose between her teeth that basically became the blueprint for the "soft grunge" look. It wasn't about being perfect. It was about a certain kind of "I just woke up like this" magnetism.
- The Vibe: 1940s Hollywood meets 1990s street style.
- The Impact: It resurrected her career when people thought she was a "washed-up tragedy."
- The Fashion: Choker necklaces, sunflowers, and lots of bleached blonde hair.
That Infamous 1995 Playboy Shoot
We can’t talk about her most provocative imagery without mentioning the January 1995 issue of Playboy. Drew was 19 at the time. She’s recently gone on record—specifically in a 2024 Instagram post titled "PHONE HOME"—to say she has some complicated feelings about it now that she’s a mother.
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She called the shoot "chaste" and "artistic," which, looking back, it kind of was compared to the hyper-sexualized standards of today. But back then? It was a scandal. Her godfather, Steven Spielberg, famously sent her a quilt for her 20th birthday with a note that said "Cover up." He even included a fake Playboy cover where she was fully clothed.
She did it because she was an exhibitionist. She felt free. She didn't think the internet would ever exist to make those photos permanent. "I thought it was paper," she joked on her talk show recently. "I didn't know it would stay forever."
Mark Seliger and the Art of the Editorial
Beyond the scandals, Drew Barrymore's collaboration with photographer Mark Seliger produced some of the most creative sexy pictures of Drew Barrymore ever captured. Their partnership started in 1993 and spanned decades.
Seliger didn't just take "pretty" photos. He put her in costumes—a topless boxer, a twisted Alice in Wonderland, a 1950s housewife. These photoshoots were about storytelling. They captured her transition from a rebellious teen to a 20-something power player.
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You’ve probably seen the 1995 Interview magazine cover where she’s holding a cigarette, looking like a total rebel. It’s gritty. It’s the opposite of the polished, airbrushed influencers we see today. That’s why these images still rank so high in pop culture history; they feel like a real person having a real moment, even if that moment was staged for a magazine.
A Timeline of Iconic Looks
- 1990: The "Pacific Heights" premiere—leather jackets and cross necklaces.
- 1993: The Guess Campaign—classic Americana with a wild streak.
- 1995: Miu Miu SS95—pioneering the "heroin chic" look but with a playful wink.
- 2003: Charlie's Angels: Full Throttle premiere—wearing a white suit with a black bra peeking out, proving grunge wasn't dead.
- 2009: The Whip It era—rocking a dip-dyed bob and McQueen gowns.
Why We Are Still Obsessed
The reason people still look for these vintage photos is simple: Drew Barrymore was the original "relatable" star before that was a marketing term. She was open about her struggles with addiction and her family drama.
When you look at her photos from the 90s, you aren't just seeing a beautiful woman. You’re seeing a survivor. She leaned into her curves, championed body positivity before it was a hashtag, and refused to fit the "skinny" mold of the time.
"I never beat myself up or forced myself to look a certain way," she told Health magazine. She knew she’d have to starve herself to look like a runway model, and she basically said "no thanks, I’d rather have wine and pasta." That authenticity is what makes her photos—even the most provocative ones—feel empowering rather than exploitative.
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Making the 90s Aesthetic Work for You
If you’re looking at these iconic Drew photos for style inspiration, there are a few key takeaways you can actually use today. The 90s are back in a big way, and Drew was the queen of that era.
- Mix Masculine and Feminine: Pair a floral slip dress with heavy combat boots.
- Don’t Fear the Dark Lip: A deep burgundy or brown lipstick is the ultimate 90s throwback.
- The Power of the Accessory: Daisies, chokers, and tiny backpacks. It sounds cliché now, but she made it look effortless.
Instead of just scrolling through old galleries, think about the confidence she projected. Whether she was posing for a high-fashion editorial or just walking a red carpet with a stuffed Mickey Mouse backpack (yes, she actually did that), she owned her space.
If you want to dive deeper into her visual history, check out her book Find It in Everything. It’s a collection of her own photography focusing on heart shapes she found in nature and everyday life. It’s a great way to see the world through her eyes rather than just seeing her through a lens.
Next Steps:
If you're inspired by the 90s look, try incorporating a vintage-style slip dress or a classic denim jacket into your wardrobe. For a deeper dive into her career, look up the "How Do You Drew" podcast, which breaks down her most iconic fashion and film moments in great detail.