Taylor Swift Makeup Looks That Completely Missed The Mark

Taylor Swift's makeup is almost as iconic as her hits. The superstar has perfected that red lip, classic look, and Swifties across the globe can't stop trying to mimic Swift's makeup routine with their favorite crimson shades and super black-winged eyeliner. 

Thankfully, the "I Can Do It With A Broken Heart" hitmaker has shared a few hacks over the years, including revealing how she draws a cat eye sharp enough to kill a man. "I do the outer corner flick first: I follow the curve of my lower lash line and draw it on as if it's an extension of that," she told Redbook in 2012. "Then I draw along my top lid and connect it to the flick."

However, despite mastering her makeup and being a beauty icon, Miss Americana isn't immune to cosmetics fails now and then. The "Shake if Off" singer has a handful of looks in her beauty book that completely missed the mark.

Taylor Swift still had a lot to learn about makeup in 2017, which made for some questionable looks when she supported Brad Paisley on his "Bonfires and Amplifiers Tour." The then 17-year-old hadn't committed to her signature red lip but was regularly doing smoky eyes instead. During a stop in California, Swift layered black eyeshadow all over her lid, particularly on the outer corner, but it needed a lot more blending and precision. The dark shade totally camouflaged her lashes, which, with the liner under her eye, made her peepers look small. The shadow also drooped below her lash line, which wasn't the most flattering placement.

Not only was the shadow too harsh, but Swift seemingly skipped several other products, including foundation, contour, and lipstick. There's nothing wrong with keeping cosmetics to a minimum, especially with flawless skin like Swift's, but such a bold eye can look unnatural on bare, or close to it, skin. This look also showed us just how important filling in and shaping the eyebrows can be to frame the face. Even the most natural made-up brow can have a big impact.

It's never a good idea to use anything other than cosmetic-grade eyeliner around the eye. Taylor Swift, though? She ignored that advice and swapped her cosmetics for a Sharpie. The beauty confessed to her faux pas on X, formerly known as Twitter, in February 2010, writing in a since-deleted tweet (via Taylor Throwbacks), "I just used a Sharpie as eyeliner in the airplane bathroom." 

Swift elaborated on the outcome in a 2012 interview with Refinery29, telling the outlet, "I don't recommend it." She echoed that sentiment when telling Elle about her error seven years later, hinting it may have happened more than once. "DO NOT DO IT," she said again. The star admitted that the effects were so bad she overhauled her skincare routine.

Swift didn't confirm to which event she wore the Sharpie eyeliner, if any. However, five days after her tweet, she was photographed at the Country Radio Seminar dinner with some very suspiciously thick-looking lines on her lids. Her usually thick and fluffy lashes appeared clumpy too, which may have been a side effect of the marker.

Taylor Swift experienced another makeup mistake in 2013 when she accepted the Pinnacle Award at the 2013 Country Music Association Awards. Though her lipstick usually seems to be sweat-, rain-, and everything-else-proof, she hadn't perfected keeping it in place that night, and that resulted in a very red chin. 

The smudging was understandable though, as Swift had a lot of people to thank. Not only did she give big hugs to her mom, dad, and brother, but the stage was littered with stars she greeted individually. Tim McGraw presented the "Blank Space" hitmaker with the gong, while she also greeted Rascal Flatts, Faith Hill, George Strait, Keith Urban, and Brad Paisley. Knowing she'd be interacting with so many people, we'd have thought her team would have tried harder to make her lips totally smudge-proof.

Two years earlier, Swift shared her secret for making lipstick last with Allure. "[Makeup artists] put on the red lipstick, then blot it with a tissue, then they put powder over the tissue and sort of press it onto your lips. Then re-apply," she said. "It turns it into a stain that lasts much longer." Swift also shared a similar method with Redbook the following year, but it didn't seem to work when it counted.

When Taylor Swift attended her first Met Gala red carpet in 2008, she needed more lash glue. The star wore unnatural-looking spidery faux lashes that began to peel away from her eye. It can be tough to get a strip lash to stick toward the inner corner unless you've really got your false lash method down, and Swift may have gotten better results from individual lashes (such as Ardell's Triple Individuals Knot-Free Short Eye Lashes or Kiss' Looks So Natural Trio Lash).

Another reason this look missed the mark? The Met Gala is all about over-the-top gowns and makeup, but Swift's glam was too understated for the event. At the end of the night, her lipstick and gloss were barely there, which made her faux lashes look out of place. She also appeared to have lost some foundation from her nose and chin, and she had fallout from her gold glitter shadow on her cheeks.

Taylor Swift had an awkward makeup moment in New York in October 2015 when paparazzi flashes bounced off the setting powder she'd applied to keep her concealer in place, making her undereyes appear a patchy, bright white. As makeup pro Benjamin Puckey explained to Teen Vogue, it usually happens when powders contain silica. "[They] work fine if you're not planning on getting photographed (especially with flash photography), but if you are, avoid these white silica-containing finishing powders at all costs," he advised. Swift and her team are pros at seeking out great cosmetics, which makes us think she wasn't expecting to be papped that night.

Swift experienced a similar incident five months earlier when she stepped out in the Big Apple with Gigi Hadid. That time was less dramatic, but the camera flashes still gave her unnatural white patches. The superstar didn't confirm which product caused the issue, but we're guessing she tossed it and shook it off.