Taylor Swift's Best-Dressed Awards Show Moments (So Far)

As pop stars sometimes are, Taylor Swift is a fairly polarizing figure. Saying that you like to sing along to her music could elicit either squeals and head nods, or groans and eye rolls. What's not up for debate, though, are the accolades she's earned, the records she's broken, and the iconic moves she's made on the business side of things. Forbes puts her net worth at an estimated $2 billion in 2026. Oh, and she's only 36 years old, as of this writing.

When she's not inking deals and causing young girls to break out into happy sobs, Swift is at Hollywood's and music's biggest awards shows. She's one star who seems to have a lot of fun with her looks — whether she's showing off those killer legs with a sky-high slit, oozing elegance in a classic ballgown, or flirtatiously playing with separates. In short, the stunning style transformation of Taylor Swift has been an impressive one, and we've got the pics to prove that she continues to slay the awards show red carpets season after season.

Back in November 2016, Taylor Swift hit the 50th annual CMA Awards in Nashville serving up dreamy dark glamour, and literally shining on stage. She wore a gown with cutouts at the midriff and sides, covered in an inky web-like print with stripes flowing this way and that. The Julien MacDonald design was so of the era and perfect for a young pop star. We especially love the strappy stilettos and the punk-rock vibe of Swift's wavy blond bob.

Who could forget the sorbet-colored crop top and maxi skirt Taylor Swift wore to the Grammy Awards in February 2016? The "Cruel Summer" singer donned a voluminous Barbie-pink skirt with a super high slit and a juicy tangerine-colored crop top. To double down on the cuteness, she'd chopped her signature ashy blond locks into a sharp short cut with bangs. We've watched Taylor Swift's stunning beauty evolution over the years, and the era of the cheeky chin bob with cherry red lips was one of our faves.

Taylor Swift graced the Grammys red carpet in February 2024 in a look that could've come out of Old Hollywood's golden era — save for a few funky, more modern touches. The strapless custom-made Schiaparelli gown featured dramatic draping, a structured bodice, a lengthy train, and lots of leg courtesy of a serious slit. Swift accessorized the dress with black velvet opera gloves and matching open-toe pumps. She kept the looking feeling fresh and fun with a '90s-era gothic choker and chains, and wet-look hair.

When Taylor Swift made an appearance at the Golden Globe Awards in January 2014, the musician channeled all the quiet glamour of an old-school movie star. She donned a strapless two-toned Carolina Herrera ballgown, the jet black sweetheart bodice giving way to a classically draped full skirt in a delicious ruby red hue. To complete the look, Swift popped on her signature scarlet lip and styled her iced latte blond hair in tight ringlet curls.

If Taylor Swift ever stars in a blockbuster superhero movie, we'll have popcorn at the ready for the look if nothing else. The outfit the star rocked at the iHeartRadio Music Awards in March 2023 was superhero meets cunning jewelry thief in the most fun, fashion way possible. Dotted head to toe in rhinestones, she sparkled from her seat in the slick hooded top, leggings, and boots combo designed by Alexandre Vauthier. And Swift's bone-straight, super shiny hair only added to the sly vibes. 

Taylor Swift slinked down the red carpet at the Grammy Awards in February 2012 in a Zuhair Murad gown that was equal parts elegant, playful, and sultry. The gold and champagne-colored creation featured a sheer overlay decked in whimsically arranged sequins, and read perfectly proper with its high neck. But when the "Shake It Off" singer turned around, she showcased a super sexy open back with a host of cutouts. The luxe look reminded us of something a princess in ancient Greece would've worn, especially when you factor in Swift's neat high bun.

We wonder if Marilyn Monroe was the inspiration for Taylor Swift's look at the MTV Video Music Awards in August 2013. Between the classic figure-hugging silhouette and the saucy Old Hollywood hair and makeup, we're totally picking up the va-va-voom vibes. Swift donned a midnight blue Hervé Léger bandage dress with a plunging neckline and a delicately bejeweled bodice. She punched up the sultry energy with the help of dark eyeshadow, thin brows, and a cherry red lip color.

If you're looking for inspo on how to style a corset top for any occasion, then pin the two-piece minty sage-colored 'fit Taylor Swift wore to the iHeartRadio Music Awards to your mood board. For the March 2026 event, Swift reached for a Wiederhoeft vest-like corset top and matching miniskirt in a translucent satiny fabric. The rose gold beading detail on the bust and at the hip added just the right amount of bling, and we're still not over the complementary, barely-there strappy sandals.

In this shimmering custom-made Gucci gown, Taylor Swift looked like a statue herself at the Golden Globe Awards in January 2024. The "Bad Blood" singer reminded us of an Old Hollywood starlet in the bright green creation with its delicate straps, sweetheart neckline, nipped waist, and overall timeless silhouette. The whole look was bold and elegant at the same time, and her dark blond hair, styled in soft waves, and the rouge-colored lips were the perfect pairing.