Taylor Swift Makeup Mistakes That Ruined Her Otherwise Gorgeous Looks

Music icon Taylor Swift has long served as style and beauty inspiration to fans everywhere, with the Pennsylvania native most recently embodying WAG glam with her Kansas City Chiefs game day looks. Still, this doesn't mean that the Hollywood figure is immune to beauty and fashion mishaps. Just as Swift has some outfits that simply didn't work, the "Cruel Summer" singer has made some look-ruining makeup mistakes over the years.

"You have to mess it up a few times before you get it right," Swift told Keds. "I had a lot of failed makeup looks that I would try in school before I ever learned how to, like, do the [eyeliner] right and sometimes I still get it wrong." While makeup is ultimately a form of self-expression, and you should be encouraged to wear what you're most comfortable with, we can all take some pointers from beauty experts to learn from the makeup mistakes of Taylor Swift.

Back in 2008, before she was the mega-superstar we know today, Taylor Swift was making her first-ever appearance at the annual Met Gala. The "Teardrops on my Guitar" singer donned a floor-length gown from Badgley Mischka featuring a glimmery, diamond-shaped design resembling mermaid scales. The eye-catching garment also had three distinct color-blocked white, bronze, and black sections under its golden detailing. Swift allowed the stunning gown to take center stage, styling it simply with her classic curls and some warm-toned eyeshadow. Unfortunately, the overall look was sabotaged by a falsie, with the strip lash becoming visibly unattached near her inner eye.

This common makeup mishap can take away from an otherwise gorgeous look, but experts have a few tried and true tips to help keep false lashes secure. For longevity, avoid applying lashes immediately after applying the lash glue. "Give the glue 10 to 20 seconds for it to get tacky," Mable Lee, creator of Velour Effortless Lashes, told She Knows. "It will make your lash application so much easier." Lee also emphasized that both ends of the false lashes should be secure, so an extra dash of glue on either end can be helpful. If all else fails, you can always tote a backup tube of lash glue to avoid the same sort of fallout as Swift.

A then-20-year-old Taylor Swift took the stage at the 2009 CMT Awards for two performances, singing her hit song "You Belong With Me" and then collaborating with Def Leppard for a rendition of "Pour Some Sugar on Me." Swift donned a slightly edgier version of the outfits worn during her Fearless tour (and future Speak Now tour) for the latter performance, wearing a black, fringed dress with gold sequins along the neckline and straps. While we love how the dress looks with her loose-flowing curls and black cowboy boots, we're not so crazy about her makeup. While Swift was aiming for a more rock 'n' roll style here, the young music star's dark eyeshadow wasn't properly blended out, sitting chunkily around her eyes in a vaguely cat eye shape. 

Blending is an important step in most eyeshadow looks, as it helps the colors transition and adds dimension to the eye. Soft, fluffy brushes are essential for this. "Take the bigger brush, without picking up any more color and use it to blend the hard edges," makeup artist Aimée Twist told Who What Wear. You can use a circular motion for blending the darker shadows often placed in the outer corner of the eye, while a V-shape motion helps blend into the crease. While Swift's stage outfit would've been elevated with these simple tips, you can take this as an opportunity to learn from the star's past mistakes. 

Taylor Swift wore a Marilyn Monroe-inspired dress to the 2011 Teen Choice Awards, with the white frock featuring a halter neckline and a circle skirt. While we love this piece on Swift, especially with her hair pulled back into a wavy ponytail, the one-toned eyeshadow was a surprising choice. Swift is known for her signature red lipstick and winged eyeliner, a look similar to Monroe's classic makeup, but she opted for a sparkly blue shadow for her award show appearance. 

It's possible that the "Blank Space" singer was referencing Andy Warhol's famous pop art rendition of Monroe, which sees her with exaggerated blue eyeshadow, or even channeling the color's popularity in the '60s and its connection to women's liberation. Still, there's something about the use of the color here that throws off the outfit. Given the light coloring of the dress, we would've loved to see Swift wear a dark or richer shade of blue for a more contrasted look. 

Playing with colorful cosmetics can make for a striking look, but it should be done purposefully. "Blending bright colors well and pairing them with neutral shades is key to making them look modern," makeup artist Jenny Patinkin told Teen Vogue, mentioning black or brown eyeliners as potential choices. Fortunately, Swift did go on to learn how to purposefully use blue eyeshadow, as seen at the Eras Tour Movie premiere and the 2023 Grammy Awards. 

Music star Taylor Swift wore a beautiful Elie Saab gown to the 2012 Billboard Music Awards, with the floor-length dress featuring a strappy bodice with lace detailing. Departing from her classic curls, the Pennsylvania native wore her hair completely straight with feathery bangs across her forehead. For the most part, we really appreciate the styling of this outfit, with Swift pairing warm-toned eyeshadow to accent the orangey-red color of her dress. The only problem is that the pop star wore little to no bronzer, blush, or contour, allowing her matte foundation and nude lip to wash her out.

While foundation and powder are great tools for evening out skin tone and creating a canvas for cosmetics, they can also leave the face looking flat if used alone. Things like blush and bronzer help restore some healthy-looking color to makeup looks. "Both bronzer and blush work together to bring life back to your complexion," Tiffany Tarazi, NYC-based makeup artist, told Byrdie. "Bronzer adds a sun-kissed warmth, while blush provides a fresh pop of color." We think a similar-toned bronzer to Swift's eyeshadow applied around the hairline and cheeks would've completed this otherwise stunning look.

Back in 2019, Taylor Swift attended the Golden Globes, appearing onstage to present the Best Original Song award beside her "Cats" co-star Idris Elba. For the star-studded event, Swift wore a sparkly, black Versace gown with off-the-shoulder straps and a pronounced slit. Along with V-shaped detailing on the bodice, the garment featured a combination of beading and transparent fabric that created a feather-like effect all over the gown. She took a minimal approach to her makeup, donning a bronzy eyeshadow and orange-toned red lipstick. We would've loved the star in some dramatic bronzer or contour here, but the lipstick shade is where Swift missed the mark. 

It can be difficult to choose the right lip color to go with an outfit, but there are some go-to methods. You should always take into account where you're going in an outfit, as some lip colors will be more suitable for some occasions than others, and experts often suggest factoring in your skin tone. Other than that, when coordinating your lip color with your outfit, opt for a shade that directly matches your clothing or use a color wheel to identify a complementary hue. Of course, you can always play around with neutrals, either in your clothing or lipstick. For Swift, we would've recommended a deep red, dark berry, or even a rich nude to suit her demure, sexy gown.