Her reputation has never been better – but her style choices could come back to haunt her
SHE might be the biggest pop star in the world with an estimated worth of over £1billion – but catch her on the street and she looks just like any old New Yorker, and there’s a good reason for this.
In 2016, Taylor was “given a new look” by Vogue’s editor Anna Wintour who said her “fashion choices” were “a little bit conservative”.
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Taylor’s 2016 Met Gala look was a far cry away from her ‘girl-next-door’ styleCredit: GETTY
Almost overnight, her lady-like ensembles with cute flippy skirts and mousy blonde hair, were transformed into a “rock n’ roll chick” with plaid shirts, vintage tees, and ripped jeans.
Anna “hoped” Taylor would “continue with this look” even after the fashion shoot was up – and Taylor stuck with the new edgy vibe for a while.
Her grungy bleached blonde hair made an impact on her music too – after all it was the ‘do she had when she met former flame Joe Alywn at the Met Gala which was referenced in her song ‘Dress’.
But even with the help of the iconic Queen of fashion – Anna Wintour – Taylor, now 33 years old, doesn’t seem to know what her style is, be it on the street or red carpet.
Some fans suggest her stylists are to blame for her “hit or miss” outfits.
Take the blue cut-out ballgown she wore for her 1989 Era’s premiere earlier this year as an example – it divided her beloved Swifties.
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Taylor’s Era’s Tour premiere outfit was a nod to the 80s decade apparentlyCredit: GETTY
One suggested the fabric had been chewed by moths, whereas another commented on her hairstyle that was a nod to the 80s and said it “gave a masculine vibe”.
It didn’t matter what she wore really, 99.9 per cent of her fans thought she looked gorgeous – but it wasn’t really very Taylor.
Having been in the public eye since 2006 as a 16-year-old country singer, Taylor has become one of the most commercially successful musicians of all time – her songs last year reached 36.6 billion streams – but her style has never gained the same level of attention.
Perhaps it is because she is so incredibly successful at what she does – that she doesn’t need to make a point of bending to what society deems as fashionable?
Andy Barr, PR and brand expert from, 10 Yetis Digital and Fabulous’s fashion expert Clemmie Fieldsend explained how Taylor’s choice of outfits keep her relatable, and her how her streetwear carefully plays off her stardom.
Andy said: “Taylor Swift may have recently had her empire valued at over a billion dollars but she is playing a savvy game when it comes to dressing like an everyday person.”
Clemmie added: “When we step out of our style comfort zone, sometimes it works and sometimes it doesn’t – but Taylor isn’t afraid to try.
“In this outfit, she visibly looks uncomfortable with what she’s wearing. The oversized jumper and boots look fits together, but the cross-body bag, not worn as a cross-body bag, makes her look like she grabbed the first things she saw.”
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Taylor mixed casual with cool with a T-shirt dress and knee-high bootsCredit: The Mega Agency
The PR expert noted: “Whilst her army of fans adore her, her carefully crafted image has had a few knocks of late thanks to the likes of the global outrage over accusations of her overzealous private jet usage and so she is clearly keen to appear just like one of us.
“One way she can understate her wealth is via the clothes that she wears and her new street style does this perfectly. ”
But Clemmie said: “In her preppy era Taylor clashed her prints a lot which suits the trend down to a tee, however this pleated mini skirt and cropped latticed shirt pairing creates, what feels like a magic eye picture.
“But for me, the clumpy brown leather boots are what’s jarring the most.”
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Dressed like a daydream walking the streets with one of her ‘girl Squad’ Gigi HadidCredit: Getty – Contributor
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Taylor swapped her sparkly Louis Vuitton boots from the Eras Tour for a more understated pairCredit: Getty
Taylor headed to the Kansas City Cheif games to support her new boo Travis Kelce recently and then headed out to dinner, but her outfit choice doesn’t scream games night.
Fashion expert Clemmie commented: “Aside from when she’s wearing her new boyfriend Travis’ jersey, Taylor never really dresses to the occasion.
“For example, here she is in denim shorts, knee-high boots and a black bodysuit – is she going to a festival, going out-out or taking out the bins? Who knows.
“Whilst there is nothing wrong with this look it’s not really giving us anything.”
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Taylor stepped out with her new boo earlier this month in biker boots and a mesh topCredit: GC Images
The couple stepped out in public for one of the first times and clearly caused a stir, not just because they were spotted holding hands, but their outfits too.
“Poor old Travis got stick for his boyband look and was compared to a member of N*Sync, but at least his 90’s look is N*Sync with Taylor,” Clemmie continued.
“Her whole outfit is like something you would have seen a Nickelodeon presenter wear way back when, but it’s not working in for today’s fashion.
“Taylor could have stopped at her all-black look and skipped the sheer top – as fashion designer legend Coco Chanel once told us you should ‘take off the last thing you put on’.
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She didn’t shy away from clashing prints meeting Gigi Hadid back in 2019Credit: Splash News
“We’ve all had that predicament when you’re heading out the door in your best frock and realise you might be cold, but instead of grabbing something plain or tonal with her floral dress she’s reached for a check blazer,” explained our fashion expert.
“The eighties style power dressing jacket with a flowery mini doesn’t seem like the perfect pairing,” a simple fashion faux-pas, or a planned tactic to make her look relatable?
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Taylor dressed up channelling her reputation era for MTV Video Music Awards 2023Credit: Doug Peters/PA Wire
This promising outfit does everything for Taylor’s best assets including her height and never-ending legs says Clemmie – but once again, a few tweaks could have been made to make it really pop.
“I LOVE this look for Taylor,” she says. “It’s grown up, sexy and really suits her. It also is very similar to Liz Hurley’s iconic safety pin dress.
“But the only thing that doesn’t match up is her mullet hairstyle and layered chain necklaces.”
Taylor is so much more than just what she wears – she holds incredible power and influence.
GQ Magazine reported a 400 per cent increase in Kansas City Kelce jersey sales after Taylor was spotted wearing one at a recent game – and it’s all thanks to her Swifties.
And Andy noted: “There is a reason why she is adored by her army of fans and this is largely that in a world where we are used to the eccentric behaviour of our celebrities, Swift just comes across as something very rare, a nice person.
“She was never going to parade around in the kind of brands and labels that distance herself from her fan base and her stylists and publicists know this.
“Her brand is strong, her style is accessible and her popularity continues to soar.”
