I recreated the makeup of iconic women from different eras

Throughout history, makeup has been used to cover imperfections, enhance natural features and express oneself. As a result, different looks and techniques have become symbolic of certain time periods.

These iconic looks tell us not only what features were desirable within a society, but also how much freedom women were granted to experiment with their appearance. In medieval times, church leaders in Europe believed makeup was immoral and sinful. However, other past cultures embraced cosmetics. The ancient Egyptians used makeup as a spiritual and magical tool, while also using it to enhance beauty.

While women still use makeup to enhance their natural beauty nowadays, more and more women find freedom in seeing makeup as an art, a creative way to express one’s individuality. As someone who adores makeup and uses it for both purposes, I decided to try out five iconic makeup looks from across history and see how I felt while wearing each of them.

Cleopatra

To begin, I started with the most ancient example of an iconic makeup look I could think of: Cleopatra’s bold eyes and lips.

I used a black eyeliner pen to line my upper and lower eyelids, bringing the wing up to meet the end of my eyebrows. I blended light green and white eyeshadow to create a gradient across my eyelids, and I used a dark brown eyebrow pencil to make my eyebrows appear bolder than usual. I contoured my face with a bit of bronzer, added a small amount of peach blush and then finished the look with a bright pink lipstick.

This was definitely the most “out there” look that I tried on. I enjoyed the dramatic contouring and bronzed cheeks, and I liked the contrast that the green eyeshadow and pink lipstick created. However, I was not a fan of the dramatic eyeliner, as I tend to only line my upper eyelid.

This look was fun to create, but it was definitely intended to emulate Cleopatra’s dramatic makeup rather than be practical for daily wear or going out.

Marilyn Monroe

To recreate Marilyn’s signature look, I started with a combo of white eyeshadow as a base and light brown eyeshadow blended in just above the eyelid creases. After filling in my brows with a dark blonde pencil, I used liquid eyeliner to create a wing that was narrow near the inner corner of the eye and thicker toward the end of the wing. After applying dark red lipstick and a bit of white powder to highlight the center of my bottom lip, I added Marilyn’s signature beauty mark with the liquid eyeliner.

This was undoubtedly my favorite look to try. After I’d applied it, I felt instantly more confident. I’d never tried a winged eyeliner that was that thick toward the end, and I liked how it made my lashes seem much more dramatic. As a fan of the quintessential bold eyeliner and red lip, I was glad I tried this look out.

Twiggy

Between trimming false lashes to fit my lower lashline and trying not to let my makeup fall into the “grunge” zone, this look was the most difficult to pull off. I loved how simple the cheeks and lips were while recreating Twiggy’s look, but I felt that the dramatic blue eyeshadow drowned out the color of my eyes rather than enhancing it, which could have been done with bronze or gold shades.

In addition, no matter what facial expression I made taking these photos, the look felt too angsty. It was fun to mess around with falsies, though, and this was the only look where they were applied to the bottom lashes.

Madonna

Out of the five looks, this was the easiest to apply. I used a bright pink lipstick and picked a blush of a similar shade, applying it slightly below the apples of my cheeks. On my eyes, I blended a lavender shade with bright orange and then used white to highlight the arches of my brows.

I enjoyed this look because it was the least restrained, and I had much more freedom with this look than the others. Madonna’s brows were slightly unkempt and wild, so I enjoyed not needing to be as precise as usual with my brows. I also did not apply falsies for this look, so it took substantially less time and effort than the other four.

Kylie Jenner

Finally, I decided to bring Marilyn’s iconic winged eyeliner and red lips into the 2010s and try on Kylie Jenner’s signature look. To emulate Kylie’s makeup, I contoured my face much more dramatically than I’m used to, and I also used a translucent powder to bake my face, which I’d never tried before.

It was interesting, to say the least, and Kylie’s look definitely required the most effort for the least result. Neither my eyes nor lips were remarkably dramatic in the final result, but the contouring and baking required layers upon layers of liquid and powder.

Out of the five, this look is definitely the most “wearable,” in fact, it’s the only look I’d be willing to wear outside of the house. No matter how well I pulled off a Cleopatra or Marilyn, this is definitely the only look I could wear to the grocery store without getting odd glances and smirks.

The lips were a bit too defined for me, as I tend to avoid wearing heavy lipsticks or glosses, but overall, this was my second favorite look. I’d try a less-elaborate version of this for daily wear, making sure to cut out a few layers and products.

After trying out these five iconic makeup styles, I was left with a rejuvenated respect for the power of makeup. Marilyn’s look felt the best when finished, as I instantly felt more confident. Twiggy’s look was my least favorite, as the lower lashes and dark eyeshadow drowned out my eyes, and I felt it made me look sad or angsty.

Recently, I’ve been using makeup solely to conceal blemishes rather than to be creative, so it was refreshing to get back into the fun, freeing side of makeup and take a break from my daily routine.