The 14 Most Memorable Oscars Beauty Looks of All Time

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Award season is upon us, y’all. 

In anticipation of this year’s 92nd annual Academy Awards (taking place on Sunday, February 9, 2020, at 8 p.m. ET on ABC), we’re taking a look back at the best Oscars beauty looks of all time. 

From Audrey Hepburn's brows to Viola Davis's lashes, here are our favorites from throughout the years.  

The 15 Most Memorable Oscar Dresses of All Time

audrey hepburn with her oscar
ullstein bild Dtl./getty images

1. Audrey Hepburn's Bold Brows (1954)

The year she won Best Actress for Roman Holiday, Hepburn stuck to her classic look: Dark, straight brows that thin to a point just at the ends. Weren’t blessed with natural Hepburn brows? Follow our ultimate guide to filling in yours.

Get the look: Tweezerman Mini Slant Tweezer ($14); Anastasia Beverly Hills Brow Definer ($23); Grande Cosmetics Brow Enhancing Treatment ($70)

barbra streisand with her oscar
ABC Photo Archives/getty images

2. Barbra Streisand's Mod Eyeliner (1969)

First things first: This voluminous bob-fluffy bangs combination is incredible. So, too, is Streisand’s mod eye makeup: Smoky liner all along the eyeline, plus some more smudged all over her crease. (If you want to recreate the look, this Lisa Eldridge tutorial is a fabulous starting point.)

Get the look: Mac Pro Longwerar Fluidline Liner ($19); Urban Decay Eyeshadow Primer Potion ($24); Natasha Denona Mini Nude Eyeshadow Palette ($25)

cher at the oscars
Hulton Archive/getty images

3. Cher's Glossy Lips (1986)

If you can pull your eyes away from this incredible Bob Mackie headpiece, you’ll see that Cher’s lip gloss is poppin’. Layered over a peachy-nude lipstick, a clear gloss adds just the right amount of shine.

Get the look: NYX Slim Lip Pencil ($4); L'Oreal Holographic Lip Gloss ($5); Stila All Day Liquid Lipstick ($22) 

madonna at the oscars
Ron Galella/getty images

4. Madonna's Red Lip (1991)

Lest you thought Madonna's Marilyn Monroe obsession was limited to her Material Girl era (which ended a few years prior to this), she channeled the blonde bombshell at the '91 Oscars, allowing a cherry red lip to make a bold statement against a backdrop of porcelain skin, bleach blonde hair and white fur. 

Get the look: E.L.F. Cosmetics Lip Brush ($4); Kopari Lip Scrubby ($16); Nars Velvet Matte Lip Pencil ($27)

halle berry with her oscar
MIKE NELSON/getty images

5. Halle Berry's Pixie (2002)

Between her signature chop, minimal makeup and before-it-was-trendy nude dress, this entire look is iconic.

gwyneth paltrow at the oscars
Ron Galella/getty images

6. Gwyneth Paltrow's Midnight Blue Smoky Eye (2002)

A far cry from her sweet light pink look at the 1999 Oscars, Goop’s 2002 look was grunge, grunge, grunge. Less expected than a classic black smoky eye, her blue version is smudgy without being sloppy.   

Get the look: Makeup Forever Eye Shadow ($17); Marc Jacobs Beauty Eye Crayon Eyeliner ($26); Tarte Creaseless Under-Eye Concealer ($26)

jlo at the oscars
Bob Riha Jr/getty images

7. Jennifer Lopez's Green Shadow (2003)

Making a strong case for matching your eye makeup to your dress, J.Lo adorned her ultra-bronzed skin with a highly pigmented swipe of minty shadow, plus a subltle nude lip (you know, to keep the focus on the eyes).

Get the look: Sephora Collection Eye Shadow ($8); Charlotte Tilbury Eye Shadow Pencil ($27); Huda Beauty Obsessions Eye Shadow Palette ($27)

charlize theron at the oscars
Ian West - PA Images/getty images

8. Charlize Theron's Barely-there Brows (2004)

It takes a brave person to rock a brow this thin, and a stunning person to somehow make it work. We’re also very into the overall monochromatic vibe.

reese witherspoon at the oscars
Lester Cohen/getty images

9. Reese Witherspoon's Retro Ponytail (2011)

The higher the hair, the closer to looking like a vintage Barbie. Heads up that recreating this ‘do will require a lot of hairspray (and possibly some extensions for a little extra oomph).

jessica chastain at the oscars
Dan MacMedan/getty images

10. Jessica Chastain's Cat Eye (2012)

Red carpets are rife with smoky eyes, which is fine (they do photograph really, really well). But it’s refreshing to see an actress deviate from the norm, in this case with a short but impactful flick of jet-black liquid liner.  

Get the look: Morphe Angled Liner Brush ($3); Ulta Matte Eye Primer ($12); Bobbi Brown Long-Wear Gel Eyeliner ($27)

anne hathaway with her oscar
Jeffrey Mayer/getty images

11. Anne Hathaway's Pink Lip (2013)

There’s not a ton to say here other than that a classic rose-y pink lip—paired with a ballet slippers-colored dress—is just really really pretty.  (Here’s how to find the best lip color for your skin tone.)

Get the look: Buxom Plumpline Lip Liner ($18); Clinique Shaping Lip Color ($20); Bite Beauty Agave Lip Mask ($26)

lupita nyongo with her oscar
Frank Trapper/getty images

12. Lupita Nyong'o's Headband (2014)

A thin, sparkly band injects a little whimsy into an otherwise classically dressed-up ensemble. Here are three other retro hair accessories making a huge comeback right now.

Get the look: Tasha ($44); Alexandre de Paris ($50); Simone Rocha ($102)

ruth negga at the oscars
Lester Cohen/getty images

13. Ruth Negga's Berry Lip (2017)

We love how Negga played around with shades of the same color, from her dress and lips to her stone-adorned headband. Her matte berry lip is super sophisticated, and works perfectly with an ever-so-slightly smoky eye.

Get the look: Jouer Cosmetics Lip Scrub ($11); Lipstick Queen Lip Liner ($18); Smashbox Matte Liquid Lipstick ($24)

viola davis at the oscars
Steve Granitz/getty images

14. Viola Davis's Mega-watt Lashes (2018)

There’s a lot to love about this look—from the sleek, center-parted hair that cascades into a curly disco-inspired fantasy to the blue under-eye liner—but Viola’s impossibly long lashes, which practically touch her brows, take the cake.   

Get the look: Shiseido Eyelash Curler ($22); Lilly Lashes False Eyelashes ($20); Too Faced Better Than Sex Mascara ($25)

sarah stiefvater

Wellness Director

Sarah Stiefvater is PureWow's Wellness Director. She's been at PureWow for ten years, and in that time has written and edited stories across all categories, but currently focuses...