Taylor Swift’s Beauty Evolution: Country Coils to Bold Red Lips

Photo from thefader.com

Since she first ascended to fame with her self-titled introductory album, Taylor Swift has evolved from a country fairytale to a glamorous pop star, with the hair and makeup looks to match each turning point in her career. It has been said before, but she is the master of self-invention. Each era is so laconically summed up in the moments preceding her album drops. Princess, girl-next-door, sparkling pop star, retro lover: there is a Taylor Swift beauty period for everyone. So, with the Midnights album released last week, and her new vibe alongside it, we at VALLEY are taking a stroll back through memory lane, analyzing her greatest beauty moments and what this latest era could signal.

Taylor Swift

Taylor burst out onto the music scene as a curly-haired innocent strumming notes — and shedding teardrops — on her guitar. As a Reading, Pennsylvania teen, her first era was heartily princess themed. With her naturally long curly hair and love for the utmost amount of glitter and sparkles on her eyeshadow and dresses, it was all fairytale and romance. Her songs spoke of hopeless romanticism and so did her wistful appearance. Soft lips, glittery eyeshadow and natural face makeup painted the stage for her beauty debut.

Fearless and Speak Now
Photo from weheartit.com

Still sticking to her romantic vibe, “Fearless” and “Speak Now” mark the time when Taylor really started to make a name for herself as a country/pop singer and songwriter in the industry. With this newfound name and impending maturity, she began to explore her beauty a little bit more. Her tight ringlet coils let loose into bouncy and barreled curls. Embracing the aesthetic of fantasy with songs like “White Horse” and “Enchanted,” her makeup looks toned down on the previously used glitters but still maintained that natural glow. There may have been boy drama, but her curls and lip gloss were always there to back her up.

Photo from femestella.com

This marks the biggest and most iconic change in Taylor Swift’s beauty. Screaming Tumblr era, the curls were left at the Speak Now tour in favor of sleek bangs. And, who could forget the famous bold red lip? There were still hints of romance in her lyrics, but with “Red’s” album cover showing half of her face in the shadows, and only her lips and straight hair in the light, Taylor painted the story of a girl with a past. With hits like “Red” and “All Too Well,” Taylor’s stark beauty transformation presented a girl with a tightened grip on her persona.  

Photo from vogue.com

In “1989,” Taylor Swift came into power as a pop star. She lost the country princess music and looks in favor of a chicer and more feminine appearance. The red lipstick grew a bit darker, her once long hair gave way to a short blonde bob and she dawned an insane number of eye-catching sunglasses on her tour. Taylor successfully hit the balance between welcoming BFF and bombshell, rising above her man-crazy rumors.

Photo from cosmopolitan.com

With the Kardashian (mainly Kanye) drama behind her, Taylor hit the scene once again, but, this time, she had a much darker persona. With the black and white album cover, and the motif of snakes in her lyrics, the old Taylor was truly dead. In this era, Taylor kept her bangs but allowed her curls to grow out once more. Yet, they appeared more muted. Eyeliner and dark eyeshadows became her best friend, and, on her tour, she embraced the boldness of a dark lip.

Photo from weheartit.com

With the flirtatiousness and dreamy visuals of this album, Taylor once again made a complete 180. The darkness of Reputation exited stage right as the rainbow aesthetic descended. Taylor leaned into her more romantic looks, being seen at music awards with rosy cheeks and a fresh face of makeup.

Folklore and Evermore
Photo from L on Pinterest

“Folklore” and “Evermore,” both surprise albums, scream “cottage core,” inviting listeners to throw on their favorite cozy sweater and gallivant through the woods. Taylor’s signature hair for this moment: a long braid down her back, emphasized by the “Evermore” album cover. Her makeup was completely natural: no bold lips, eyes or cheeks to be seen.


We haven’t seen much of this era quite yet, but it is evident that Taylor takes on a retro vibe and reintroduces her signature glittery aesthetic. Sapphire blues and sparkling silvers (especially eyeshadows) are the trademarks of this new period with a dash of her signature red lip for balance.

Taylor Swift continues to push the beauty boundaries of the industry, evolving from look to look as her music changes. As “Midnights” mania continues to soar, we at VALLEY are more than excited to see what comes next (maybe a tour announcement?). Which era is your favorite? Tweet or tag us at @VALLEYmag with your most beloved Taylor Swift beauty moment.


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