Taylor Swift's Best Preppy In Plaid Looks

Taylor Swift has experimented with different styles throughout her career, curating her fashion and album aesthetics into distinctly well-known eras. Still, since she began dating Travis Kelce in late 2023, Swift has had a mini style transformation, with plaid being a recurring pattern in recent months. There are many fan theories about the significance of the eye-catching motif, with some Swifties theorizing that the pop icon is rerecording her debut album, while others are certain she's hinting at the impending re-release of her album "Reputation."

While we're confident that the pop icon always has something exciting in store for the future, the truth is that plaid has long been a staple of Swift's wardrobe, with the "Cruel Summer" singer constantly changing how she styles the pattern. From the casual button-ups of her "Fearless" and "Speak Now" eras and the cozy scarves of "Red" to the preppy streetwear of "1989" and the vintage statement pieces of "Folklore" and "Evermore," it's truly been a versatile mainstay of the music star's style. Over everything else, Swift has managed to leave a lasting impression with her plaid, preppy looks.

Taylor Swift's "1989" era really saw the pop star adopting some iconic preppy-and-plaid outfits. While the "Blank Space" singer had sported both plaid garments and vintage-inspired pieces before this, the two style elements really came together in Swift's NYC era, as seen in this outfit from November 2014. While out with girl-squad member Karlie Kloss, Swift wore a camel-colored coat with a simple red and blue plaid over a black dress. She paired the items with polka-dotted tights, purple-toned Louboutin booties, and a designer handbag in a matching color.

Skater skirts became a major part of Taylor Swift's wardrobe during her "1989" era, with the award-winning artist still occasionally sporting the silhouette today. Her December 2014 outing in New York City is a great example of how effortlessly the pop singer would style the garments into iconically preppy outfits. Swift looked super cozy in a navy tartan skirt, turtleneck, and duffle-style coat, styling the ensemble with purple tights, brown oxford pumps, and a knitted green beanie. This particular combo, especially the colored tights, feels very of the time, but it's still a Swift look that we remember fondly.

Taylor Swift's "Midnights" era, which was marked by the release of her tenth studio album in October 2022, also saw the music icon adopt some preppy plaid garments for a retro-inspired look. The outfit that Swift wore in a countdown-style TikTok video shows off this sort of style, with the "Lavender Haze" singer combining a beige, orange, and yellow sweater vest with tan slacks. Instead of clashing, the two plaid patterns come together for a sort of '70s off-duty professor look.

Plaid-centered fan theories have been swirling around Taylor Swift ever since she sported a yellow tartan dress at the 2024 VMAs — a controversial look that landed on Women's list of Swift's worst eras-coded outfits. Even so, it seems like the singer has been slowly revitalizing the pattern since late 2023, as seen in this preppy tweed look from December. While out in Manhattan, Swift sported a matching coat and mini-skirt from Stella McCartney, with both garments featuring a brown, gold, and black plaid. The designer items were styled with a black V-neck top, tights, and pointed-toed heels.

Since dating football star Travis Kelce, Taylor Swift has been serving up some ultimate WAG glam in her game-day looks. This November ensemble, worn for the Kansas City Chiefs and Denver Broncos game, simultaneously ranks as one of her standout preppy-and-plaid outfits. It might not be the most conventional choice for a football game, but Swift sure looked killer in the matching blazer and mini-skirt from Versace. She styled the red-and-black houndstooth pieces with a black corset, knee-high boots, and gold jewelry. A wispy updo and her signature red lip really completed Swift's look, leaving us wondering what the music star is planning next.