When it comes to my style (both beauty and fashion), I’ve always been inspired by the movies, music, and pop culture that was big around the time of my teenage years and early adulthood. Sure, my frontal lobe was still forming, but the ’90s and early 2000s were a gold mine for beauty and fashion inspiration. Hello, 1999’s Jawbreaker? There were the dark, vampy lips that defined Drew Barrymore’s ’90s look and Aaliyah’s mesmerizing metallic eye shadow in the music video for “Try Again.” At the time, I knew they were cool, but I didn’t have the foresight that I’d be trying to re-create them 20 years later. As I step into 2025 wearing my very ’90s platform sandals, it’s the perfect time to channel that same energy and pay these iconic looks homage while also giving them a fresh, modern twist.
Even if we refer to this makeup as ’90s and Y2K inspired, a lot of it is completely timeless to me. Maybe it’s just the nostalgia factor or my refusal to move on, but they perfectly capture the mood and culture of their eras. Take, for example. Gwen Stefani’s bold red lips and sharp, ultra-thin brows. Yes, she may be more commercial and mainstream these days (she even released a country-inspired album), but at the time, she helped define a generation of beauty rebels who gave the finger to traditional beauty standards. Even though blue eye shadow ebbs and flows in the realm of beauty trends, I consider Christina Ricci’s frosty blue eye shadow in Buffalo ’66 something I can replicate whenever I want to channel a retro, moody vibe. Bottom line: These looks weren’t just about aesthetics—they were about badass attitude, self-expression, and unapologetic individuality.
If you want to join me in re-creating legendary beauty moments from the ’90s and 2000s (Cruel Intentions! Josie and the Pussycats!) in 2025, keep reading for all the inspo you need, plus the makeup products that will get you there.
1. Drew Barrymore’s “’90s Bad Girl” Style
(Image credit: S. Granitz/WireImage via Getty Images)
Barrymore’s style in the ’90s was nothing short of legendary. With her ultra-thin brows (yes, I lovingly blame her for my skinny-brow trauma); tousled, bleach-blonde hair; penchant for body glitter; and, most importantly, vampy lipstick, she embodied effortless red carpet cool. Deep, moody lip colors were on-trend at the time, but on her, they felt rebellious and chic, perfectly capturing the angst-ridden aesthetic of the decade’s grunge and riot grrrl icons. She did hang out with Courtney Love back in those days, after all.
MAC Lip Liner in Spice ($25) was her go-to back then, but even though it’s still around, people have pointed out that today’s version is much warmer than the OG. A new alternative that comes very close to the original Spice is Mob Beauty’s Smooth Precision Waterproof Lip Liner in M1990($22). However, I say it’s time to elevate Barrymore’s allover lip liner look and go for a plush dark lipstick, like Charlotte Tilbury’s K.i.s.s.i.n.g Satin Shine Lipstick in Night Crimson. Oh, and to get that body glitter look that she loved to wear, go for a shimmering body oil, like Sol Body’s Body Glitter Glow Oil in Moonstone ($10) so you can nourish your skin and glow at the same time. Now, all you need is a slip dress and baby clips, and you’re good to go.
Charlotte Tilbury
K.i.s.s.i.n.g Satin Shine Lipstick
SOL Body
Body Glitter Glow Oil
2. Kate Winslet in Eternal Sunshine (2004)
Kate Winslet’s Clementine in Eternal Sunshine is a heroine for anyone who doesn’t believe in hair color loyalty. While her parade of ever-changing hair colors stole the show, don’t skip on her makeup. Her flushed cheeks, pinky-brown lips, and subtle black eyeliner complemented her effortless-meets-ethereal look. That quirky, romantic vibe her hair and makeup give off is truly unique. Special shout-out to Peter Owen, who did the wigs, and Kyra Panchenko, the makeup artist!
Thanks to Clem, I’m seriously considering making the leap to orange hair in 2025, but in the meantime, I’ll pay homage in other ways. First on the list is finding a subtle but pretty blush. Stila’s Convertible Color Lip & Cheek Cream Blush in Peony ($25) is a good choice. Second? I’m getting an equally low-key but lovely lip product, like Prada Beauty’s Moisturizing Lip Balm in Noisette ($50). Also, I want bright-orange eye shadow to satisfy my orange-hair craving. I’m going for it, and About-Face’s Matte Fluid Eye Paint in Spectre ($16) is perfect.
Stila
Convertible Color Lip & Cheek Cream Blush
Prada Beauty
Moisturizing Lip Balm
about-face
Matte Fluid Eye Paint
3. Aaliyah in the “Try Again” Music Video (2000)
The early 2000s were all about the future—there were lots of metallic shades in makeup and clothing at the time. Aaliyah’s silver, smoky eye shadow in the music video for “Try Again” is the epitome of futuristic glamour. Paired with her flawless skin, glossy lips, and sleek outfits, her shimmering silver lids, courtesy of her makeup artist Eric Ferrell, created a look that felt both ahead of its time and perfectly of-the-moment.
I’ve recently discovered my holy-grail silver eyeliner: Em Cosmetics’ Silver Lining Eyeliner ($26). It’s creamy, making it easy to apply, and it gives off the pop of sparkle I’ve been looking for my whole life. If I want to do a “subtle” tribute to Aaliyah, I’ll wear this solo. For a full look, Huda Beauty’s Icy Nude Eyeshadow Palette ($69) has every shade I need.
EM Cosmetics
Silver Lining Gel Eyeliner
Huda Beauty
Icy Nude Eyeshadow Palette
4. Sarah Michelle Gellar in Cruel Intentions (1999)
Kathryn (played by Sarah Michelle Gellar) in Cruel Intentions is the ultimate mean girl because she makes her moves in silence. Her makeup was all about subtle seduction, which tracks since she literally seduced everyone around her. Think perfectly sculpted brows, smoldering neutral eyes, and a brownish-berry lipstick that radiated power and poise. Makeup artist Brad Wilder was responsible for the look, which was sophisticated yet approachable—even if the character was intimidating—making it perfect for everyday wear.
When I look at Kathryn’s makeup, I see a polished version of the eye look I tried to do in junior high and high school when I wasn’t a baby goth. Before I discovered winged eyeliner, it was all about brown eye shadow and matching eyeliner. Nars’s Quad Eyeshadow in Koh Rong ($52) is a grown-up version of the single-pot shadows my friends and I shoplifted back then. A creamy eye pencil, like Monica Blunder Beauty’s Eye Deal Liner Pencil ($28), is a nice upgrade from the stiff eye pencils we had to use with a lighter to melt them so they went on easier.
Nars
Quad Eyeshadow Palette
Monika Blunder Beauty
Eye Deal Liner Pencil
5. Christina Ricci in Buffalo ’66 (1998)
Ricci’s baby-blue eye shadow in Buffalo ’66 is a look that lives in my brain. Paired with her head-to-toe pastel outfit, the angelic makeup was the cherry on top of this… unconventional love story. What makes this look really stand out is its boldness. Blue eye shadow is not something that a lot of people want to pull off, but it can be strikingly chic. You just have to find out how to make it work for you. Go bold or go subtle; blue eye shadow is surprisingly versatile in that way IMHO.
Gucci Westman was the key makeup artist for the film, and she went on to launch Westman Atelier, her luxury makeup brand, in 2018. Unfortunately, there isn’t a blue eye shadow in the lineup, but you can pick up Westman Atelier’s Eye Want You Mascara ($45) for a fluffy lash look after re-creating Ricci’s dreamy blue eye shadow with ColourPop’s On Cloud Blue Baby Blue Powder Palette ($6).
Westman Atelier
Eye Want You Lengthening + Volumizing Clean Mascara
6. All the Women From Josie and the Pussycats (2001)
The makeup in Josie and the Pussycats was pure Y2K fun. The satirical musical comedy was way ahead of its time, but it’s also a good film to watch when you want to shake things up in your makeup routine and/or embrace your inner pop star. We had everything everywhere all at once—glitter, rhinestones, bright colors, neutrals, frosty lids, and glossy lips from makeup supervisor Rosalina Da Silva and leopard print, bell-bottoms, crop tops, and even stripper heels from costume designer Leesa Evans.
Skip the neutrals and go big and bold with sparkly gems and glitter wherever you can put them. In one scene, Parker Posey has on rhinestone-studded lashes, and About-Face’s Volume Up Faux Embellished Lashes in Mirrorball ($12) are a cool, pearly take on this maximalist lash look. Paint your lids with Stila’s Glitter & Glow Liquid Eye Shadow ($25), then decorate your face with Bakeup Beauty’s Beauty Playbox ($24) for a magical gem-filled look.
about-face
Volume Up Faux Embellished Lashes
Stila
Glitter & Glow Liquid Eye Shadow
BAKEUP Beauty
Beauty Playbox
7. Gwen Stefani in the ’90s
This is cheating since it’s a look I’m always wearing, but I have to put it on my list: ’90s Gwen Stefani! I’ll never forget the first time I heard No Doubt’s “Just a Girl” while I was at the movies watching Clueless, which I was also seeing for the first time. Clearly, it was such a big moment in my life. Soon after, Stefani was all over MTV and inspiring girls everywhere to put on red lipstick for the first time. Her look during this era was all about contrasts: bold red lips, sharp brows, a cat eye, and an edgy attitude. It was punk rock– yet pinup-inspired makeup that blended retro glam with a rebellious twist. Obviously, I’m still obsessed with it decades later.
Stefani’s Gxve Beauty has its own classic red lipstick—Original Me Clean High-Performance Matte Lipstick ($13)—so it makes sense to channel her through her own product. Stefani’s makeup artist at the time, Gregory Arlt, has said she wore a lot of MAC’s classic reds, including Russian Red ($25), which now has an upgraded formula that’s more comfortable and lasts longer. A real modern twist! Stefani’s bold lips and winged eyeliner are seen as dramatic for some, but the simplicity of the overall look keeps it wearable. At the same time, it’s a combination that makes you feel confident and powerful—not simple at all. There’s a reason why I adopted it as my own signature look.
GXVE Beauty
Original Me Clean High-Performance Matte Lipstick
MAC
Macximal Silky Matte Lipstick
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