Recreating Iconic Lip Looks From The Last 100 Years

Which pout do you think is the most iconic?

Let's talk about lips, baby. Not just your everyday, run of the mill lips. I'm talking iconic lips from decades gone by. The sort of pout that defines a person's look. There have certainly been many such lips over the years, and I lament that I didn't have enough time or resources to discuss and recreate them all for you today. I do think I've compiled a healthy sampling, though, so let's get to it.

Clara Bow - 1920s

Roaring '20s silent film star Clara Bow--aka "The It Girl"--easily has one of the most iconic looks of all time. While she was known for her curly hair and sleepy, baby doll eyes, her lips often stole the show.

Clara wore a petite pout with an exaggerated Cupid's bow and fuller bottom. For this look, I applied concealer across my lips and blended out. I then used Aveda's Nourish-Mint Lip Liner in Fire Maple to overdraw my Cupid's bow. Instead of extending the line all the way to my outer corners, though, I stopped short to create Clara's pouty effect. I also overdrew the bottom by just a hair, creating more of a round shape, and then filled in with the liner.

Joan Crawford - 1930s

I still remember the first time I saw a picture of Joan Crawford. Her look was so striking, so unconventional; I wasn't quite sure what to make of it all. And if I'm being perfectly honest, I wasn't really a fan of the overdrawn, smeary lips she's so famous for. That said, they've grown on me. There's something so carefree and luscious about them that I can't help but want to stare at them all day long.

To create the famous Joan Crawford smear, I opted for ModelCo's Lip Duo in Unboxed, a creamy, pliable mauvish-brown. Joan's lips are overdrawn mostly on the outer edges of the top lip, and then along the bottom lip to create a more horizontal line.

Marilyn Monroe - 1950s

There's not much I can say about Marilyn Monroe that you don't already know, so I'm going to move right on ahead to talk lips. Oh, those lips. Lips that were so heavy with product that girlfriend probably spent calories just holding them up. Her makeup artist, Allan Whitey Snyder, gets the credit for Marilyn's entire look. Whitey was painstakingly thorough in his makeup choices for Marilyn--red, waxy lips included.

To get that full, Marilyn pout, I lined my lips with a dark, wine-y red, slightly overdrawing at the outer corners to create more of a round shape. I then filled in with a lighter, brighter shade of red. From there, I blotted, then reapplied both again. And then I blotted again, and reapplied twice more. The reapplication process to build up pigmentation and volume was very much a signature part of Marilyn's lip look. Finally, I applied a sheer, waxy gloss on top and then dabbed a bit of white powder onto my bottom lip. The white powder not only created a fuller effect for Marilyn's lips, but also made it seem like they were always catching the light. And duh, I had to draw on her famous mole.

Twiggy - 1960s

Let's be straight here: Twiggy was known for her eyes. However, while those drawn-on, extended lashes were her trademark, her lips were also noteworthy. One thing that set Twiggy apart, in particular, was her playfulness and propensity toward color experimentation. Perhaps we should credit her makeup artists, but she certainly had a way of ensuring all that color and product never wore her.

One of my all-time favorite shots of Twiggy is of her wearing a two-toned lip, a look which saw a bit of a comeback this year. For this look, I simply applied Maybelline's Color Sensational Vivids in Electric Orange on the top and blotted, then applied NYX Butter Gloss in Vanilla Cream Pie on the bottom.

Tim Curry, Rocky Horror - 1970s

OK, here's my unconventional inclusion for this post. I went back and forth on this one, but ultimately I had to include Tim Curry's funky lip from cult classic Rocky Horror because…FUN. Victoria actually suggested this one, so she gets all the points, cool lady that she is.

This was actually one of the easiest looks to recreate. All I did was line my lips with Urban Decay's Super Saturated Ultra Intense Waterproof Cream Eyeliner and fill them in with Rimmel's Show Off Lip Lacquer in Big Bang, an ultra glossy, bright red that stays wet and juicy.

Pam Anderson - 1990s

Oh, '90s, with your super lined nude lips. Pamela Anderson often opted for frosty, fleshy lips and a slightly darker lip liner. She's since changed her look, but we'll never forget her Baywatch era.

Recreating this look was actually pretty difficult, as Pam's lip shape is quite different from mine. She's certainly more toothy, and her upper lip is fleshier while my bottom lip is fuller. In any case, for this look I lined my lips with Rimmel's 1000 Kisses Stay On Lip Liner Pencil in Tiramisu and then filled in with Rimmel's Moisture Renew Lipstick in Nude Delight. I followed up with a sheer, frosty gloss.

Angelina Jolie - 00s and Beyond

There really isn't anything, makeup-wise, that Angelina does to make her lips so iconic. Instead, it's her questionable fullness that sets her mouth apart--lips so voluminous and pouty that you wonder how they don't burst. They also have a sort of cracked-like effect to them, almost as if they are forever chapped.

Making my lips up as Angelina's was no easy feat. I used lots of product, including shadows and highlighters both on and around my lips. To begin, I applied a nude liner that exaggerated my Cupid's bow and bottom lip. I then filled in with a sheer, pinkish-nude gloss. After blending the liner into the gloss, I applied brown powder under my bottom lip to create a shadow effect. I then applied highlighter just below that, for more depth, and blended the two. I also applied shadow and highlighter around my Cupid's bow and philtrum (hers is quite pronounced). Finally, I applied a bit of white powder to the bottom lips, then drew on "cracks" with a brown shadow at the center of my top and bottom lips.

  • I know there are lips I neglected (Greta Garbo, ScarJo, Cindy Crawford, Kerry Washington, Blondie, Lucille Ball, Judy Garland, Cate Blanchett, Kylie Jenner)… Which ones would you have included?
  • Which iconic stars have inspired your look in the past?