The early to mid-twentieth century saw the popularization of Old Hollywood makeup: perfectly curled hair and red lipstick, worn by stars including Marilyn Monroe, Rita Hayworth, and Elizabeth Taylor. Over time, the aesthetic has evolved and become a red carpet staple. These days, Old Hollywood beauty generally refers to gentle waves, a dark lip, smokey eyeshadow, and dark liner.
Ahead, the prettiest modern versions of the Old Hollywood beauty aesthetic.
Gwen Stefani
Gwen Stefani's '90s and '00s makeup is a perfect example of a slightly modernized "Old Hollywood" look. The platinum blonde hair, sharp black cat-eye, thin eyebrows, and well-lined red lip are all near-matches to the original aesthetic, with modern hair and clothing to feel more current.
Blake Lively
Matching your lips to some other part of your outfit, as Blake Lively is doing with the feathery stole that's just visible in this photo, is a great idea. In this case, the red lipstick is softer than other options on this list, and the eye makeup isn't as maximalist or dramatic.
Marlene Dietrich
Extremely shaped eyebrows aside, Marlene Deitrich's look here isn't that out of the box if you'd like to implement a more modern version. Her blush application is lower on the cheeks and higher on the cheekbones than you often see, so take into consideration for your own face.
Lauren Cohan
Part of the success of this look is Lauren Cohen's classic hairstyle. She also picks a red lipstick that matches beautifully to her dress. Because she has darker hair and eyebrows, she can pull off a more substantial mascara and eyeliner application.
Andra Day
Andra Day loves mid-century glamour, and her styling proves that it's a perfect match for her. The lip color is a rich maroon, and the articulated lashes and dramatic cat-eye all look extremely precise. The softer brows and gentle curls add some contrast.
Lily Collins
Lily Collins has thick, beautifully shaped eyebrows, and they're often the focal point of her face. As such, this look keeps things quieter everywhere else: no sharp eyeliner on her eyes, and a lip color that's just deeper than nude. The look is still striking without feeling like too much.
Dita Von Teese
Dita Von Teese has made vintage Hollywood glamour an important part of her aesthetic—for decades now, at this point. Thus, she's a perfect example of "Old Hollywood" makeup that feels timeless: a rich red lipstick, full eyelashes, gentle cat-eye, and minimal blush.
Hayley Atwell
Hayley Atwell demonstrates that smoothly-styled hair is as important as makeup when pulling off a classic look (and that a tan is a nice way to update the aesthetic). Additionally, a deep fuchsia pink lip color works just as well as a deep, vivid red.
Natalie Portman
Natalie Portman doesn't always opt for a red lip, but when she does, it looks fabulously dramatic. Her wine-colored lipstick works beautifully with her dark hair, and she opts for brown eye makeup instead of black for a slightly less maximalist vibe.
Jayne Mansfield
Jayne Mansfield, originally framed as a newer Marilyn Monroe, developed her own look and persona. The bronzed skin, coral pink lipstick, and slightly longer hair all speak to the Old Hollywood style but also show how much variation there was even at the time.
Amy Adams
Amy Adams often goes for head-to-toe classic in her red carpet looks, and her hair and makeup are no exception. Here, the emphasis is on the eyes instead of the lips; you can still achieve an "Old Hollywood" look with a lighter lip, so long as the hair remains wavy and the eyes are still smokey.
Sophia Loren
The Italian actor's version of "Old Hollywood glamour" is softer and more subtle than the American version. The red lipstick is so soft (and a much more muted shade than that of the dress) and the eye makeup light so as not to fight with the dark, dramatic eyebrows.
Issa Rae
Issa Rae opts for an Old Hollywood-inspired updo here. The plum colored lip gloss is deep and dramatic without being over the top, which allows those gorgeous long fake eyelashes to take center stage. The ultimate effect is surprisingly balanced and bold at the same time.
Jessica Chastain
Jessica Chastain's red hair plays an integral part of her classic aesthetic: it's often styled in glamorous waves, like this, and adds natural drama to her look. Even though the colors on her lips and eyes are matte, they're enlivened by the auburn hue.
Elizabeth Taylor
The young Elizabeth Taylor had a distinctive look that was a bit different than other starlets' in Hollywood. But that's what makes it so striking: her dark hair and eyebrows are the perfect complement to a deep blue-red lipstick and lots of mascara.
Reese Witherspoon
When Reese Witherspoon opts for a deeper, darker makeup look (instead of her more signature nude), it's a delight. Even with a bright pink lip and matching cheeks, she keeps her smokey eye makeup a soft brown. She still looks like herself, just with slightly more drama.
Keke Palmer
Keke Palmer is literally channeling Old Hollywood here, including with the long black gloves. This is a perfect mid-red lip color and the smokey-eye/cat-eye hybrid is a classic matte black. The only thing that's even slightly modern about it is the hair.
Scarlett Johansson
Old Hollywood makeup doesn't have to be overly-defined—so if you want a more casual look, just use Scarlett Johansson as your guide. The soft burnt sienna color on the lips is echoed with the caramel colored eye makeup, but everything is blurred and gentle.
Angelina Jolie
While a lot of looks on this list are all about the eye makeup, Angelina Jolie does the opposite and places more emphasis on her lips. Putting on a bold cherry red lipstick and keeping things minimal on her eyes and cheeks really enhances the fullness of her mouth.
Lupita Nyong'o
Lupita Nyong'o looks even more incredible here than she usually does, which is really saying something. With a deep red color on the lips and a red blush to match, plus a lot of black eyeliner and a touch of gold on the brow bone, the whole thing is luminous.
Emma Stone
Emma Stone really dials up the drama to match her short haircut, and the effect is dazzling. (It almost feels like a modernized Audrey Hepburn!) That pretty pink lipstick is another nice alternative to bold red, and you can keep the dark eye makeup confined to your mobile lid—like this.
Rita Hayworth
Perhaps one of the most quintessential examples of Old Hollywood makeup, Rita Hayworth's look was somehow delicate and dramatic at the same time. You don't have to make your eyebrows as thin as hers, but the volume of the eyelashes and the perfect shade of red lipstick are a must.
Kim Basinger
Kim Basinger channels a little Old Hollywood at the 1990 Oscars (she was nominated, and subsequently won, for her role as an escort and Veronica Lake lookalike in LA Confidential, so this pays homage to that). The soft application of her makeup and messy curls look like an awesome '90s interpretation of the theme.
Ana de Armas
Ana de Armas actually played Marilyn Monroe, and she occasionally channels that aesthetic on the red carpet. As with many looks on this list, the makeup matches her soft brunette hair, with pretty pink lipstick and complementary, sparkly brown eyeshadow.
Taylor Swift
Taylor Swift often favors a red lip on the red carpet, but what differentiates a look like this is the capital-d Drama. That glossy lip color is gorgeous, and the matching cat-eye shape brings a nice cohesion. Matching your eyeliner to your jewelry is expert-level precision.
Madonna
Madonna's early aesthetic had an "Old Hollywood with a twist" vibe to it: curled platinum blonde hair, medium red lipstick applied a little bit messily, mild red-tinted blush to match, and a little messy eyeliner on the top lid. The look feels like a throwback but also fresh and new.
Lana Del Rey
With her vintage, retro style, Lana Del Rey has a romantic Old Hollywood vibe. Here, the scarlet lips and long matching nails (both of which are similar in color to her rich, flowing brunette hair) reads a bit "dramatic and undone" in a beautiful way.
Grace Kelly
Grace Kelly wasn't always Old Hollywood in the traditional sense (as in, she didn't always favor a deep red lip, opting for a softer look). But, she did channel the aesthetic from time to time, keeping her general aesthetic in mind while adding a darker lip color like this.
Rihanna
Bold and daring is Rihanna's modus operandi, which makes an Old Hollywood style perfect for her. The emphasis is on the red lipstick here, and the star adds in a dash of light eyeshadow to her smokey eye. A thoroughly modern, slicked-back hairstyle helps bring this into the modern day.
Audrey Hepburn
Audrey Hepburn's look was a study in contrasts: her hair was very short, but it was still soft and feminine. In much the same way, this red lip color is extremely soft, but lined to perfection. And her thick brows are clearly defined without looking too dramatic.
Olivia Rodrigo
This is one of the coolest modernized Old Hollywood looks of all time, in my opinion. This ombre glossy lip on Olivia Rodrigo is such a standout that, when paired perfectly with a soft cat-eye and pink-red blush, channels retro-futurism effortlessly.
Marilyn Monroe
The pinnacle of Old Hollywood glam! Often imitated, never duplicated, Marilyn Monroe embodied so much with her makeup. It's a little messy and even imperfect at times, but it's also so balanced and soft (that lip color is perfect) that it looks expertly tailored for her face.
