Taylor Swift Is in Her Princess Diana Style Era: Biker Shorts, Dad Sneakers and Sunglasses

The casual and comfortable look is one that will never go out of fashion.
Princess Diana and Taylor Swift.

Princess Diana and Taylor Swift.

From one style icon with a cult-like following to another, Taylor Swift is in her princess Diana fashion era. The “You Belong With Me” singer stepped out in the New York City September heat in a casual and comfortable outfit that pulled from the late British royal’s signature streetwear aesthetic that will never go out of “Style” (pun intended).

Swift wore an oversized Shania Twain graphic T-shirt paired with black biker shorts, chunky New Balance dad sneakers and dark green frilly-hem crew socks. The 33-year-old accessorized with round black sunglasses, a white baseball cap, a stack of necklaces, dainty bracelets, gold rings and a brown purse.

The 12-time Grammy Award-winner, who is currently in the midst of her constantly sold out “The Eras Tour,” was spotted walking in Manhattan’s Greenwich Village on Oct. 3.

Taylor Swift

Taylor Swift.

“I think that as much as you should be creative and experiment, there are certain things I know are fads, and so I try to steer clear of most of the obvious ones,” Swift told Glamour of her style. “I play the tape of my life forward and don’t wear the things that my kids or grandkids will make fun of me for wearing. For me, it’s important to be comfortable. Being comfortable means that no one’s going to be able to pull a fast one and take a picture of me that they’ll deem to be embarrassing. I don’t want to wear something so short that I’m scared there will be a wardrobe malfunction.”

The Princess of Wales, who died in 1997 at the age of 36, regularly wore the biker shorts, baggy top and athletic shoe combo as her signature look long before it was a mainstream athleisure outfit. She was most famously photographed in a gray-and-crimson Harvard sweatshirt as well as her blue Virgin Atlantic crewneck, which she began to wear almost every day to decrease the value of paparazzi pics.

Princess Diana.

Princess Diana.

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Ananya Panchal


Ananya Panchal is a NYC-based Lifestyle & Trending News writer at SI Swimsuit. Before joining the Swim team, the Boston University Alum worked for culture & entertainment beats at Bustle, The San Francisco Chronicle and the TODAY Show. When Ananya is not writing or doom-scrolling on social media, she can be found playing sudoku, rewatching One Tree Hill or trying new restaurants. She's also a coffee and chocolate (separately) enthusiast.