10 Times Taylor Swift's Killer Legs Couldn't Save Her From These Awful Outfits
Taylor Swift is the queen of writing songs that make everyone going through a heartbreak or an evolutionary moment feel instantly understood. Honestly, what would "The Summer I Turned Pretty" be without Swift's tracks swelling in the background every single time something monumental happened? Her music has garnered her a slew of awards as well an extremely dedicated fandom.
But no human is perfect, and that goes for Swift too. While she's turned out so many unforgettable hits, her style record hasn't always followed the same flawless track. Of course, she has gone through a gorgeous style transformation over the years, but there have been and continue to be many outfits that would land Taylor Swift on the worst-dressed list.
The outfits we've selected stand out even more, because they are leggy looks, and Swift is known for her killer legs. Whether it's a slit couture gown or a casual mini skirt on her day off, her long limbs are usually the centerpiece to her ensembles. But her best assets were overshadowed by some total fashion missteps. From seriously unflattering silhouettes to "Tomb Raider" cosplay vibe outfits, these are some of the awful outfits Taylor Swift's killer legs couldn't even save.
Taylor's too-cutesy alphabet look
Taylor Swift showed up to the 2014 MTV Video Music Awards in an awfully awkward blue-hue romper by Mary Kartanzou. The playful alphabet print and the seemingly heavy fabric looked more like a rug for a classroom than red carpet couture.
Even for the VMAs, this look felt a little too juvenile, and the silhouette appeared stiff and unflattering on the pop star. While many fans were hopeful the outfit was an Easter egg hinting at her next era, no cryptic and clever messaging could save it. While her legs looked amazing, they were seriously the only things going for this outfit.
This look gave off Tomb Raider cosplay vibes
When Swifties with a good sense of humor unite, they love to discuss Taylor Swift's least flattering looks. This "Tomb Raider" cosplay vibe outfit just might be on the top of many Swifties' worst-dressed lists.
Whether she wanted everyone to know how much she loved Rachel Platten's "Fight Song" or she was really feeling like a badass female action hero for the day, this ensemble was seriously overwhelming. With the harness, the studded Louis Vuitton top handle bag, and the dark brown booties that didn't even go with the outfit, there was just way too much going on.
Her attempt at futuristic goth girl was too much
In 2016, Taylor Swift had the honor of sitting as co-chair for the Met Gala, and she seemed to be dead-set on making a serious fashion-forward statement. As a global pop star should, she rocked a custom Louis Vuitton mini snakeskin dress and debuted her first-ever platinum blonde hair look.
The dress had bold side cutouts and she paired the look with knee-high lace-up sandals. While the look was fitting for the year's theme, Manus x Machina: Fashion in an Age of Technology, it went a little too far. The edgy ensemble felt overwhelming and it seemed like Swift was trying too hard to make a statement with a completely new look.
Her oversized and underwhelming holiday stage look
Taylor Swift appeared on stage during the 99.7 NOW! POPTOPIA concert in San Jose in 2017, wearing yet another confusing look. She sang her hits while rocking a sheer mesh top layered under an oversized plaid crop top with high-waisted shorts that appeared to be velvet and Dr. Marten-like metallic Michael Kors boots.
While it was another outfit that showcased her killer toned legs, the oversized, shapeless fit made the ensemble unflattering and just not very stage appropriate. Even for a casual concert, the look seemed unfinished and it felt as if comfort was prioritized over style. The edgy vibes were there, but the overall effect was more messy than show-stopping.
When the ruffles looked like they were swallowing her
For the 2019 Billboard Music Awards, Taylor Swift stepped onto the red carpet in a lavender mini dress by Raisa & Vanessa. The dress featured the most dramatic ruffles and lace insets, and while those details might be eye-catching, it completely overwhelmed her figure and hid all of her best features.
To be fair, this dress would be impossible for anyone to pull off gracefully. The layers added too much bulk, shortened her neck, and masked her elegant silhouette. The only saving graces about the dress were its stunning color and how it really made her legs shine, but even those outfit highs couldn't rescue Swift from this awful look.
When her choice of shorts and shoes didn't do her any justice
We're all for fashion-forward moments, and Taylor Swift certainly tried one at the 2020 NME Awards in London. She showed up in a Monse pinstripe blazer and white shirt concoction with matching pinstripe shorts and accessorized the look with a Jimmy Choo crossbody bag and tie-up white boots from Gianvito Rossi.
The look was definitely bold and different from her usual style at the time, but the proportions felt a bit off. We wish her stylist spent a little more tailoring the outfit to flatter her frame. The choice of a tie-up ankle boot wasn't our favorite, as it clashed with the shorts that sat at an awkward length and shortened her otherwise gorgeous legs.
When she threw on a blazer and killed the vibe
Taylor Swift's sexy sheer black lace catsuit by Sarah Gensburger at the 2021 Rock and Roll Hall of Fame induction for Carole King was almost an absolute showstopper! The look was everything from next-level edgy to daring and the Louis Vuitton ankle chain boots were chef's kiss.
But then she threw on a boxy Saint Laurent blazer over the catsuit and the outfit just got lost in translation. The blazer's awkward length made the ensemble feel top-heavy and choppy and it quickly muted the risqué boldness of the one-of-a-kind catsuit. We really wish she would've gone with a full length coat, preferably in leather, and this look could have been one for the books.
When she gave serious Green Goblin energy
Taylor Swift dazzled at the 2023 iHeartRadio Music Awards in a custom Alexandre Vauthier Haute Couture ensemble. From the pointy boots to the hooded jacket, everything was sparkling, green, and bold. The form-fitting crystal-embellished pants perfectly showcased her long and lean legs, giving major leggy vibes.
But despite the flawless silhouette and the fashion-forward concept, the extra pointy detailed boots and the hood over her head really gave Green Goblin bride energy. Even Swift's killer legs couldn't save the day, but we must say if anyone could try and pull off this daring crystal look, it had to be Tay.
When it looked like she borrowed her dad's suit jacket
Taylor Swift was spotted in November 2023 in the city walking side-by-side with fellow artist, Gracie Abrams, who has also had quite the stunning transformation. It looked like a day off for the two, and both of their outfits exuded comfort over anything vibes, which we love. But if we had to pick an awful casual outfit that even her legs couldn't do justice for, this is one of the looks.
While we appreciate the color scheme she was going for, the length of the white dress and way oversized navy blazer completely swallowed her amazing figure and made the silhouette too boxy. The mini dress would've flown better with a more form-fitting blazer, an oversized cardigan, or perhaps even a trench coat.
When she maxed out on flashiness
Taylor Swift took time out of her busy schedule to cheer on Travis Kelce at the AFC Championship Game in January 2025, and she took flashiness to another level. Maybe it was the influence of her luxury-brand-loving fiancé, but she showed up in a jacket and beanie that was overwhelmed with the Louis Vuitton logo.
Perhaps her flashiest outfit to date, the overload of the iconic LV logo and classic monogram-pattern made the look feel more costume-like than anything, which was very unusual for our girl. She even covered up her amazing legs with distracting bright red tights. "Red" is one of our favorite albums, but Taylor's version of style here misses the mark.