Emily Ratajkowski Wore Cowboy Boots and a Baseball Cap Just Like Princess Diana
When it comes to fall dressing, no one has yet done it better than Princess Diana, whose sporty yet chic looks have been replicated by the best dressers countless times over the years. So it should come as no surprise that with the temperatures dipping in NYC, celebs are looking toward the late Princess of Wales for outfit inspiration.
The first to do so in 2022 is Emily Ratajkowski, who masterfully combined cowboy boots, relaxed jeans, an '80s-style leather bomber jacket, and a baseball cap this weekend for a walk around SoHo with her son, Sylvester. While we can't know for sure if the model had Diana in mind when putting the look together, anyone who's familiar with the princess's sartorial archive will notice the similarities.
On Emily Ratajkowski: vintage Keith Haring Television Head Businessman Leather Jacket ($8019)
The outfit looks especially reminiscent of two looks of Diana's: one worn in April of 1989 to pick up her sons, Prince Harry and Prince William, from school in Notting Hill, and the other to attend an event at Guards Polo Club. For the former, she wore a tweed blazer with a white sweatsuit, brown cowboy boots, and a flat-brim blue hat. The latter saw the princess in a British Lung Foundation crew-neck, acid-wash jeans, a plaid blazer, and the same cap and boots.
With the fifth season of The Crown now out on Netflix, Diana-inspired looks are bound to be even more popular than usual this fall. Follow EmRata's lead by re-creating the two iconic outfits below all season long.
Shop cowboy boots and baseball caps like Princess Diana's:
Everyone at Who What Wear is obsessed with these.
Next up: EmRata Wore a $40 Zara Skort With the Boots on Every Editor's Fall Wish List

Eliza Huber is currently the Associate Editorial Director at Who What Wear. She joined the company in 2021 as a fashion editor after starting her career as a writer at Refinery29, where she worked for four years. During her time at WWW, she launched Go Sports, the publication's sports vertical, and published four (and counting) quarterly issues tied to the WNBA, Formula One, and more. She also created two franchises, Let's Get a Room and Ways to Wear; profiled Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter for WWW's monthly cover features; and reported on new seasonal trends, up-and-coming designers, and celebrity style.