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Taylor Swift earned the right to sing a song titled “Style” after spending years in the spotlight, but with so many opportunities to get dressed up came the inevitability that she was going to make some inappropriate fashion choices. She also has one of those “Champagne Problems” that celebs have to deal with: The pressure to keep serving up new looks for fans to admire — or brutally roast.

Unfortunately for Swift, she risks becoming a sartorial snooze if she finds a cardigan that she loves and re-wears it constantly. “I’m in a predicament where I can’t wear a dress twice or else it’s pointed out in magazines, so unfortunately I have to shop for dresses all the time,” she told Harper’s Bazaar in 2012. Then there’s her status as an influencer. She has a reputation to protect, and her apparel choices are one way to carefully cultivate the image she desires. “The reality is what you wear matters. If you’re a singer and on TV and in the living room of some 12-year-old girl, she’s watching what you’re wearing and saying and doing,” Swift told Billboard in 2011.

Swift said she didn’t even like baring her midriff back in the day because she didn’t want to distract from her music. However, she’s lived through several fashion eras since then and has become more comfortable taking style risks. Unfortunately, she’s not a clothing mastermind who nails her look every time.

Was she a cowgirl or a Disney princess?

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When Taylor Swift became famous, she was a country music girlie. In 2006, she released her debut single bearing the name of fellow musician Tim McGraw, and she seemed destined to follow in the footsteps of his wife, Faith Hill, with a long career as a female country star with crossover appeal. But sometimes her outfits made it look like she was suffering from an identity crisis. The chiffon dress she performed in at the 2007 Academy of Country Music New Artists’ Party looked like something a Disney Channel starlet would wear on the red carpet. It had scalloped layers, ruffles, and sparkles — the type of design trifecta that appeals to tweens who haven’t quite grown out of their Disney princess phase. But there were no Cinderella slippers on her feet. Instead, she paired the frilly garment with cowboy boots.

There wasn’t just disharmony between Swift’s outfit and her footwear because they were from two totally different style realms. Her dress was a vivid aqua color, while her boots were powder blue — and the two hues clashed terribly. She’d later realize this wasn’t the best look, but in a 2015 interview with Elle, she revealed that she doesn’t regret it. “I’m not going to sit there and say, ‘Oh, I wish I hadn’t had corkscrew-curly hair and worn cowboy boots and sundresses to awards shows when I was 17’ … It was part of me growing up,” she said.

Random letters on a romper

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For the 2014 MTV Video Music Awards, Taylor Swift rocked a blue Mary Katrantzou romper that was daringly short in the back. But the cut of the leg openings wasn’t what made the garment a questionable choice for the singer — it was its pattern of random, embroidered letters. They were gold and dark green, and some were positioned next to one another in a repeated, unfortunate pairing: VD. There was also a DC and a Q, so if QAnon had existed back then, the political conspiracy theory’s true believers surely would have concocted some wild explanations for what the letters meant. Instead, it was Swifties who found themselves trying to puzzle out the alphabet pattern.

Swift is so good at creating secret messages for her fans to decipher that some Swifties likely missed a few of the Easter Eggs in her Eras Tour. She has to know that her fans have come to expect this behavior, so it was a bit devious of her to wear an outfit covered with letters that could be construed as some sort of secret code. While her poor, frustrated fans put their sleuthing skills to the test, critics trashed the look. “What do the letters on Taylor Swift’s romper spell: ‘This looks bad on me,'” read one tweet. “Maybe if we re-arrange the letters on Taylor Swift’s VMAs outfit … it will tell us what it is,” wrote New York Times fashion critic Vanessa Friedman.

Why Taylor Swift had to borrow Ryan Seacrest’s coat

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Taylor Swift ended 2014 by braving the chilly weather in Times Square. For her “Dick Clark’s New Year’s Rockin’ Eve” performance, the “Fearless” singer rocked a tiny black crop top, black leggings with silver stripes down the sides, and high-heeled boots. She also had on a sparkly silver blazer when she took the stage, but she removed it right before she started singing “Shake It Off.” After she stopped moving, she couldn’t shake off the biting cold. “I’m absolutely freezing. This was the wrong choice,” she told host Ryan Seacrest. He responded by kindly offering the shivering performer his coat.

Seacrest handed his microphone to Swift. Ever the consummate professional, he continued interviewing her as he took off his jacket. While it was the singer who was not appropriately dressed for the weather, she joked, “Are you just stripping? This is a family show. My god, this is so inappropriate!”

Seacrest didn’t just have to give up his warm outerwear because Swift didn’t have her own cozy coat to put on after her performance — his chivalrous move also made it more difficult for him to do his job. “I realized all of my communication equipment was attached to it,” Seacrest recalled to Us Weekly. “So, I couldn’t really communicate with anybody in the production.” That’s one December night he probably doesn’t want to go back to.

She regrets her prom princess era

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Taylor Swift knows that some of her early designer ensembles were more appropriate for slow dances on a gymnasium floor than strolls down a red carpet. When Yahoo! Life asked the “Today Was a Fairytale” singer about her most regretful fashion decision, she revealed that there is more than one gown she isn’t nearly as enchanted by now as she was when she picked it out. “I think I missed prom too many times, so I would wear dresses that looked like you would wear them to prom. Princessy, pastels … I can’t remember one, I just see them all as a blur,” she said. In her 2015 interview with Elle, Swift called this her “fairy-tale phase.”

As an example of one of these frocks fit for a fairytale character, Yahoo! Life shared a photo of Swift at the 2007 CMA Awards. She was wearing a pale yellow gown with a beaded bodice and satin skirt. Swift looked like she was cosplaying as Belle from “Beauty and the Beast” — if the Beast had trampled all over the Disney princess’ skirt and Plumette the feather duster during their dance around his ballroom. Swift’s skirt was wrinkled and had feathers randomly tucked into its folds. It also looked a bit deflated, and the color of the dress totally washed Swift out.

Her Grammys wardrobe mishap

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Folding flowers inside sheets of wax paper and pressing them between the pages of her favorite books to preserve them seems like something Taylor Swift would do, but turning this old-timey hobby into a dress wasn’t the best move. For the 2021 Grammy Awards, Swift wore a semi-sheer Oscar de la Renta mini dress covered with embroidered floral appliques in a variety of colors. It had long sleeves and a high neckline, and there was nary a “Blank Space” to be found on the garment. The amount of flowers was a bit overwhelming, with one X user comparing it to the May Queen dress that Florence Pugh wears in “Midsommar.”

It wasn’t the most figure-flattering frock, and Swift’s suede, rose-hued Christian Louboutin sandals had thick ribbon ties at the ankles that shortened her long legs. This detail combined with the dress’ high neck created a severe silhouette.

It seems that Swift went for a whimsical fairy maiden but wound up channeling Granny’s garden instead. However, the biggest reason her $9,000 dress was a bad decision was because it was so fragile. As reported by People, Swift suffered a wardrobe malfunction when the dress tore beneath her right armpit. She should have chosen a garment made of sturdier stuff, knowing that there was a high likelihood she’d be doing a lot of hugging, celebrating, and award-hoisting after her historic album of the year Grammy win.