Taylor Swift and Dianna Agron’s Friendship Fashion Timeline: Iconic Shoes & Red-Carpet Looks

Taylor Swift has built a reputation not only as a record-breaking musician but also as a masterful storyteller.

Beyond her chart-topping hits, she delights fans by weaving hidden clues into her lyrics, interviews, and even her red-carpet appearances—sparking endless conversations about the meaning behind her choices.

Swift & Agron Bond: Black Embroidered Dress & Sequin Crop Top

Taylor Swift and Dianna Agron have sparked years of fan theories about their close bond, but beyond the speculation, both stars continue to captivate with their style—Swift in a chic black embroidered halter dress and Agron in a shimmering sequin halter crop top paired with sleek separates (Credit: Matt Crossick / PA Images / INSTARim / Cover Images and Xavier Collin / Image Press Agency)

This passion for decoding has made her fanbase, the Swifties, some of the most observant in pop culture. Over the years, their curiosity has extended beyond the music to her close friendships, including her bond with former Glee star Dianna Agron. While neither Swift nor Agron has ever addressed speculation about their relationship, their public appearances together—and their distinct fashion moments—have continued to intrigue fans and style watchers alike.

Taylor Swift and Dianna Agron first crossed paths in the early 2010s, when Agron was starring on Glee. They quickly became friends, often spotted at the same events and even celebrating birthdays together.

Dianna at Shiva Baby Premiere: Oscar de la Renta Gown & Stuart Weitzman Heels

As their friendship drew attention, Agron continued to showcase her signature red-carpet elegance. At the Los Angeles premiere of Shiva Baby on April 1, 2021, the actress—who stands 5 feet 5 ½ inches (166.4 cm) tall and wears a US shoe size 7—proved once again why she’s a style favorite.

She opted for a more sultry look in an Oscar de la Renta gown. Proof that understated designs can still command attention, the off-the-shoulder gown featured a thigh-high slit for drama and fluttery sleeves for a touch of romance.

She completed the look with a Tyler Ellis clutch and classic ankle-strap heels, keeping her makeup neutral and her styling pared back.

Dianna Agron looking gorgeous in an Oscar de la Renta off-the-shoulder dress with black suede ankle-strap heels at the premiere of Shiva Baby on April 1, 2021 (Credit: Faye Sadou / Media Punch / INSTARimages)

Swift and Agron appeared close for several years, but over time, fans noticed they were rarely seen together. That shift sparked speculation about what had changed.

Taylor at 2022 VMAs: Crystal Oscar de la Renta Gown & Custom Louboutins

Taylor Swift made a dazzling arrival on the red carpet at the 2022 MTV Video Music Awards in Newark, New Jersey, on August 28. The 12-time VMA winner, who picked up Best Long Form Video for All Too Well (Taylor’s Version) that evening, turned heads in a crystal-embellished Oscar de la Renta gown from the Resort 2023 collection. The halter-neck silhouette featured bold cutouts around the bodice, adding a modern edge to the sparkling design.

Standing 5 feet 9 ¼ inches (175.9 cm) tall and wearing a US shoe size 9, Swift completed the look with metallic silver Christian Louboutin ‘Bombina Pampilla’ sandals. Her heels echoed the dress’s shimmering crystals, designed with a T-strap silhouette adorned with dangling embellishments.

She finished her ensemble with Lorraine Schwartz jewelry and crystal appliqués accenting her eye makeup, balanced by her signature red lip.

Also in Oscar de la Renta, Taylor Swift stunned in a crystal-embellished naked dress with Christian Louboutin custom metallic heels at the 2022 MTV Video Music Awards (Credit: BauerGriffin / INSTARimages / Cover Images)

Fashion Meets Theory: From Wonderland Lyrics to Coordinated Style

Many Swifties have looked to Taylor’s music for hidden meanings, speculating that certain lyrics reflect shifts in her friendships. Wonderland, from her 2014 album 1989, is one song often linked by fans to Dianna Agron. References to “falling down the rabbit hole” were interpreted as nods to Agron’s love of Alice in Wonderland and her past tattoo inspired by the story.

While the lyrical theories remain unconfirmed, the fascination underscores how closely fans connect Swift’s storytelling to her real-life relationships—and, by extension, the fashion and red-carpet moments she shared with friends during that era.

Speculation intensified when fans noticed similar dynamics in Swift’s later friendships, particularly with model Karlie Kloss. As a member of Swift’s high-profile “squad” alongside Selena Gomez, Cara Delevingne, Hailee Steinfeld, and Martha Hunt, Kloss often appeared in coordinated looks with Swift, offering plenty of off-duty and red-carpet fashion moments that fueled comparisons to her earlier bond with Agron.

Taylor & Karlie in NYC: Gingham Shirtdress with Oxford Heels & Chic Ballet Flats

On April 3, 2014, Taylor Swift and Karlie Kloss stepped out together in New York City, giving fans a glimpse of their off-duty style. Swift looked polished in a Cynthia Rowley gingham shirtdress in berry, paired with black tights, a Cuore & Pelle Caterina handbag, and brown oxford heels.

Kloss kept her look casual and chic in a belted gray coat layered over Frame Denim Forever Karlie skinny jeans, finishing with Elizabeth and James Hoyt sunglasses and classic black Repetto Cendrillon ballet flats.

Taylor Swift, in a burgundy plaid shirtdress with brown oxford heels, and Karlie Kloss, in a belted gray coat with black ballet flats, were spotted walking together in New York City on April 3, 2014 (Credit: ACE / INFphoto)

The pair had an ill-fated friendship similar to that of Swift and Agron’s, which seemed to have the same curt ending.

Though Taylor Swift has never addressed her sexuality point-blank, she has only publicly dated men, and she has been in a romantic relationship with actor Joe Alwyn since 2017.

However, Swift has been an outspoken ally of the LGBTQIA+ community. She even dedicated her song You Need to Calm Down to members of its community.

To wrap up, both Taylor Swift and Dianna Agron have delivered standout shoe and style moments that continue to inspire fans well beyond the theories surrounding their friendship. From red-carpet gowns paired with iconic heels to everyday chic in boots and ballet flats, their fashion choices remain a point of fascination.

Taylor Swift & Dianna Agron: Best Shoe and Fashion Highlights