Some inappropriate outfits Taylor Swift wore that we can’t believe were revealed…

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.

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

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