Every time Taylor Swift leaves the house, she makes headlines with what she wears.
The 14-time Grammy winner’s custom red carpet looks routinely top best-dressed lists, while the more affordable pieces she incorporates into her street style and social media outfits tend to sell out, well, swiftly.
She even single-handedly made the friendship bracelet the year’s most in-demand accessory, thanks to a passing mention to the beaded bauble in one of her songs.
But while Swift’s massive musical achievements aren’t up for debate, her personal style has long split critics and fans alike.
While some clamor to copy her outfits and appreciate her dedication to dressing in line with each of her musical eras, others have claimed she’s “literally immune from slaying” and “lacks the depth of personality” required to make more editorial looks truly sing.
One fan, Cookie Cohen, even launched an Instagram account (@youbelonginthis) dedicated to Photoshopping fashion-forward looks onto the songwriter.
With a number of Swifties (plus a few Swift-agnostic staffers) on the Page Six team, we gathered at the office for a critical but kind discussion on the global superstar’s ever-evolving and occasionally polarizing wardrobe — from our all-time favorite outfits to those to which she should’ve said no.
Elana Fishman: As a diehard fan of Taylor Swift’s style who’s spent entirely too much money purchasing items from her closet, I’m happy to kick off and moderate this conversation. Let’s start with her look from last night’s 2024 VMAs, since it’s fresh in everyone’s minds.
Tamantha Ryan: I wasn’t a fan, but I thought it was nice of her to switch up the bright red lipstick.
Melissa Minton: When she showed up in that high-low plaid Dior outfit with the strappy opera-length leather gloves, I have to admit, I thought it was one of my least favorite things she’s ever worn. But then, she changed into a sequin-covered and embellished Monse minidress and, in my opinion, it was the absolute best she’s ever looked.
That dichotomy really encapsulates Swift’s style, which has never reached the ultimate high-fashion highs that some industry darlings strike on a regular basis.
Kristin McNamara: While I wouldn’t have chosen this VMAs look for her, I didn’t hate it, either. It was a costume, and the VMAs is an awards show you can have some fun at. It was definitely a choice, but she looked hot — that much is not up for debate!
Elana Fishman: It wasn’t one of my personal favorite red carpet looks she’s worn, but I applaud the risk she took — and you’re totally right, Kristin, about the VMAs being the place for that. That plaid look actually read as very Vivienne-coded to me, which is super in line with her corseted-and-pleated Taylor’s “Tortured Poets Department” aesthetic (with a side order of “Reputation” edge).
Moving on from the VMAs specifically, I’d love to hear everyone’s thoughts on her red carpet style more generally.
Kristin McNamara: I’ve been a Swiftie since I was 15 years old. To put my adoration for her into perspective, “New Year’s Day” was my wedding song, my dog’s name is Willow, and I went to the notoriously pricey Eras Tour three times last summer. That being said, I’ve never liked Taylor’s style. I think she gets it wrong a lot.
Ally D’Aluisio: Sometimes — like when she wore the green Gucci gown to the 2024 Golden Globes — she looks amazing. Other times, like at the 2024 Grammys, there’s a lot more room for questions. I often find that there’s just something a bit off with her more high-fashion choices, whether it’s the hair, the makeup or the shoes. But maybe that’s why I find her so relatable; how does one always have the perfect outfit? It’s nearly impossible.
Nicki Cox: Yes! When she does a red carpet, I feel like there is almost always one element that could be changed to make it dramatically better. For example, at the 2024 Grammys I felt like if she had done something a bit more simple with her hair, the entire look wouldn’t have felt as busy. Whereas at the 2024 Golden Globes, she went for a bit more simple look — by her standards — and looked stunning. It was truly one of my favorite looks of hers, but was still fun and bold, given the color.
Elana Fishman: I agree about the green Gucci at the Globes — that dress fit her like a glove, and the color was spectacular. It’s one of my all-time favorite red carpet looks of hers; no notes. I also agree about her Grammys look; the Schiaparelli gown on its own was beautifully draped, and I actually really liked the gloves, but I would have preferred to see it with different shoes (maybe in white?) and sleeker hair.
To your point, Ally, I totally agree about these little “off” elements making Taylor more accessible — quite a feat when you’re arguably the most famous woman in the world. And I do think it’s all done by design.
I often hear fashion people comparing Taylor’s style to Beyoncé’s, for some reason, but they’re completely different artists. Beyoncé does Fashion with a capital F, but her brand isn’t accessibility. She’s basically a musical deity; untouchable and perfect.
Meanwhile, Taylor’s relatable, deeply universal lyrics are what made her millions of fans in the first place. She writes songs about falling in love with the wrong people and never learning from her mistakes. Perfection’s never been her brand.
And when it comes to her fashion, she’s in on the joke. Remember when she admitted to accidentally wearing her shirt backwards, or the time she poked fun at the fact that she keeps dressing like Paddington Bear?
Personally, I’d feel alienated if she pivoted to wearing only couture, despite the fact that a star of her stature could absolutely go that route. And I think it’s genius that her street style looks always tend to include an item or two that’s actually affordable, so fans can join in on the fun.
Ally D’Aluisio: She kills it with her street style. I bought that Aupen Nirvana bag she wore on her date night on Travis [Kelce]! Even though she’s the biggest celebrity in the world, her street style feels attainable since she mixes high with low.
Nicki Cox: I do love how accessible it is, but I think if she opted for more elevated basics that were tailored to her, it would make a world of difference.
That said, I feel like she has really upped the ante in recent weeks when it comes to her everyday wear. The look she wore to the US Open was perfection! It felt true to her, but also slightly elevated and chic.
Tori Schneebaum: I think Taylor’s style is at its best when she isn’t trying too hard to make an outfit work. Every time she wears The Row, she looks unreal. She has super long legs, and can pull off slacks and high-waisted pants like none other. And when she and Travis hard-launched and she was in that simple Versace corset? So good!
Elana Fishman: We can’t discuss Taylor’s style without mentioning its ties to her many musical eras — and the Easter eggs! What are everyone’s thoughts on her dropping fashion clues and dressing to fit a specific sound?
Melissa Minton: She originated the idea of hiding clues about her career in everything she does, which includes her outfits, and thus invites scrutiny over not just every item, but also its color and style name. So perhaps Taylor isn’t looking to top a best-dressed list, but rather investing in a long piece of performance art.
Does she intentionally choose a chunky loafer when a sleek, pointed-toe pump might be more in line aesthetically? It’s hard to know.
Nicki Cox: Taylor sees herself as a storyteller and every choice she makes — including fashion — is related to her work and brand. She isn’t seen unless she wants to be seen, which means most of her outfits carry deeper meaning. Enter the Easter eggs.
As a fan, I love the game — but I also feel like it sometimes limits her looks, because she has to find something that fits into a very niche idea.
Ally D’Aluisio: Her fashion is performative, but in a much different way than that of avant-garde artists like Lady Gaga, Doja Cat or Chappell Roan. She uses her outfits to send messages that are clear to fans, but are still so much more subtle than those of a meat dress, body paint or full drag.
Elana Fishman: OK, any hopes and dreams for Taylor’s style — things we wish she’d try?
Kristin McNamara: I wish she would go more simplistic and streamlined, but stick with this sexier era she’s stepped into recently.
Tori Schneebaum: I would love to see her in more Prada. I think if she opted for something more simple but sophisticated, like a Prada Re-Nylon minidress or a white Loewe logo tank with an oversized blazer and jeans, it would be such a great look.
Melissa Minton: It’s clear than when she wants to, she’s able to pull off the quiet luxury look — like in her “Tortured Poets Department” promo photos, another highlight in my book.
Elana Fishman: I loved that shoot so much too. Final thoughts, anyone?
Nicki Cox: I love that she’s not trying to be anything she’s not. She wears what’s true to her — regardless of what people think of how she dresses.
