The Most Stunning Hair and Makeup Looks in Oscars History

The Oscars is the pinnacle of award season: exclusive, prestigious, and more formal than any award shows that come before it. Where VMAs and Grammys looks lean edgy and at times outrageous, Oscars fashion and beauty is classic: perfectly styled hair, glowing skin, extravagant jewelry. No beauty look at the Oscars comes without hours of work, meticulous planning, and top-tier makeup stylists and makeup artists—and as you'll see from this list, it shows.

Madonna

If you're going to go as modern Marilyn Monroe to the Oscars, be like Madonna and really lean in (also, a smart way to channel her bold aesthetic and still stay within dress code). The bold black eyeliner and cool red lipstick is unmistakable, and very striking.

Charlize Theron

Imagine going to the Oscars as a bronze goddess, and then literally winning a golden statue (in this case, Charlize Theron won for Monster). I don't love the blonde brows—even though it's in keeping with her character—but the gentle waves in her hair, perfect tan, and no-makeup makeup is spot on.

Goldie Hawn

Goldie Hawn has been honing her look for a long time, and here we see a youthful iteration of her iconic hair and makeup. She's only in her early 30s here, but the floral clip and the more pristine curls (pre-dating her softer waves) make her look even more youthful.

Zazie Beetz

This hairstyle makes a lot of "best of" Oscar hairstyle lists, and for good reason. She was apparently inspired by Eartha Kitt, and apparently has minimal product in it aside from a ($12!!) finishing mist. Braiding her hair the night before and then unravelling them helped give this incredible texture.

Billie Eilish

Billie Eilish's striking and shocking beauty choices are much-beloved, in part because she's always willing to experiment (even at the most formal events). Here, her raven-like tresses end in a ’50s-style flip, drawing comparison to fellow singer Joan Jett.

Sophia Loren

What I always find so fascinating about Oscars beauty looks is that you're often competing against the statue itself, which is so shiny and eye-catching that it might possibly outdo you. But when you're Sophia Loren, you just channel your classic cat-eye makeup and then you're all set.

Winona Ryder

Winona Ryder was and is the gold standard for the short, spiky pixie—it was all the rage in the '90s, in large part thanks to her—but this softer, ridged, '20s inspired version is such an elevated styling of that classic cut. I wish she wore it like that more often.

Cate Blanchett

If you're wearing some of the most expensive jewelry to grace the red carpet (this set totaled $18 million) it helps to wear makeup that's not fighting with it. Cate Blanchett wisely chooses simple black eyeliner and a nude lip, so as to better complement her stunning earrings.

Florence Pugh

For the woman who debuted a literal buzz cut at the Met Gala, you need something equally avant-garde for the Oscars. I loooove this silvery blonde color, and the visible roots are clearly quite thoughtful (i.e., not sloppy) and match the thick, perfectly tailored brows.

Drew Barrymore

Some people refer to Drew Barrymore as "the queen of the '90s," and that has never felt more apt than in this picture. The short bangs, the curly bob, the body glitter, and let's not ever ignore the daisies she has tucked behind her ears—the symbol of the decade. Oh, and the thin eyebrows we all regretted.

Sienna Miller

Sienna Miller has given us many a gorgeous Oscar beauty look—and this one is certainly not her most over-the-top. But I love the deceptively simple execution of it: the soft braided hair, the smoky but not intense eyeshadow, the peachy nude lip and minimal blush. Yes.

Issa Rae

There were a few topknots on the 2024 Oscars red carpet, but Issa Rae's was the most striking (and probably the tallest). With the overlapping, interlocking twists, with deep brunette and lighter cinnamon interwoven, it's an actual work of art complemented by the pink and brown hues in her makeup.

Julia Roberts

It's like Julia Roberts came to the Oscars with the innate foreshadowing that she was going to win the Oscar: her ultra-thick updo is the star here, lending an impressive gravitas to her look, and her makeup simply highlights her gorgeous features without trying to compete.

Michelle Yeoh

To win her Oscar, Michelle Yeoh went sparkly in all the right ways. It's a little hard to see in this photo, but she actually has on a glittery headband that complements her waterfall earrings. She kept her makeup a soft and youthful pink, and the whole vibe is that she's floating along the red carpet.

Meryl Streep

A lot of the entries on this list are going to be actors after they won, I'm realizing. If you're unfamiliar, Streep had her hair back a lot for her intense role in Kramer vs. Kramer, so this loose and wavy hairdo is the nice update she probably needed (and a good reminder that she's not her role).

Sharon Stone

Before she was known as the high-low fashion queen of the Oscars, Sharon Stone was still giving us her trademark cool-chic style at the event. The red lip is perfect, but I'm more entranced by the semi-choppy, asymmetric bob that's styled prettily but not in an overdone way.

Lauren Hutton

To match her Grecian dress (which you can't see in this photo but is multicolored in pastel hues), Lauren Hutton attended the Oscars with traditionally '70s hair and makeup. It's simple, beachy waves, minimal eye makeup, and a good amount of blush. May we all aspire to this kind of casual perfection.

Gwyneth Paltrow

Gwyneth Paltrow's now-iconic pink dress was a deeply feminine statement on the red carpet. So, to balance out the aesthetic, her hair is carefully and precisely slicked back—and it works. Imagine this with a high, curly updo? It doesn't have the same effect.

Diana Ross

Technically, this is not a red carpet look for Ms. Ross, as she's (obviously) performing onstage for the ceremony. But it's Diana in her '80s prime, with her gorgeous natural hair matching the sparkly magnitude of her dress, and her makeup simple and striking.

Jane Fonda

I just really enjoy this photo. Jane Fonda, holding her Oscar, and also looking exactly like the enormous Oscar behind her—so meta. Even her highlighted blonde hair and shiny lip gloss are getting in there to complete the look: she's shining head to toe.

Lupita Nyong'o

Like others on this list, this whole slideshow could just be pictures of Lupita Nyong'o (she's given us a lot of great Oscars beauty looks!). Her stylist apparently suggested the headband to Larry Sims, her hair stylist, as a last-minute update to the look. But it's the perfect addition to her dress.

Elizabeth Taylor

I have put Elizabeth Taylor's tiara on many a throwback fashion list—I can't help it, it's so characteristic of the actor to have a literal crown on her head during formal events. Technically that's her husband Mike Todd's Oscar, but no one's even paying attention to the statue. Her curls and simple makeup make her look like a queen.

Julianne Moore

I love Julianne Moore's red carpet beauty. This is probably the richest, fullest iteration of her auburn hair, which (considering how soft and muted her dress is) is welcome injection of drama to the whole look. Pairing red with soft pink in the lips and cheeks is the perfect complement.

Lucy Liu

Going with a bold red dress, Lucy Liu could have easily gotten away with a nude or petal pink lip. But instead she found almost the exact same shade (with a little glitter, of course, because it was the early 2000s) for a matching but not matchy beauty look.

Raquel Welch

If you're a pretty legendary bombshell (with a reputation to maintain!) and you're going to the Oscars, channel Raquel Welch here and make it look like you have a literal wind blower underneath you to lift up your curls. (She's probably just turning dramatically, but in my mind she's just blessed like that.)

Zendaya

This whole look on Zendaya was inspired by Cher, and so—because the actor-singer always gives it 110 percent—her hair is long and luxurious, just like Cher's. Much like Raquel Welch decades earlier, people literally asked if she brought a leaf-blower to the red carpet, because her curls floated gracefully in the soft breeze.

Audrey Hepburn

One of the major plot points in the Oscar-winning Roman Holiday is that Audrey Hepburn's character cuts her hair short to appear less princess-like. The hair would stick with Hepburn for much of her career, here adding a little youthful surprise to her otherwise traditional floral gown.

Zoë Saldaña

The color blush doesn't work on everyone—but it works so well on Zoë Saldaña that she should consider wearing the color 24/7. This whole look skews deeply romantic, from the soft curly updo to the barely pink lip gloss to the perfect brown smokey eye.

Cindy Crawford

Cindy Crawford's red Versace dress naturally took center stage on the red carpet (the second most famous design, next to Liz Hurley's paperclip dress), but her surprisingly neutral makeup and hair is a nice contrast, I'd argue. Going with a matte pink lip color is an especially inspired choice.

Michelle Williams

Michelle Williams' mustard-colored dress (rightly) took up a lot of attention at the Oscars; it's arguably one of the best dresses from the event, ever. But you need a striking color on top to balance the vividness in the dress. This bold red was the answer.

Halle Berry

Halle Berry's Oscar dress is also in the hall of fame, so to speak. But I will direct you to her makeup—beautiful, glimmery pinks—and the spiky, slightly disarranged look of her hair that almost makes the look feel a tiny bit "undone." It's top-tier.

Grace Kelly

You can't see it in this photo, but Grace Kelly's gown is actually a pistachio green color (and lavish silk to boot—it's reportedly one of the most expensive gowns in Oscar history). So a fresh face of minimal eye and cheek makeup and a pink-red lip is all she needed.