Emily Ratajkowski Wore Cowboy Boots and a Baseball Cap Just Like Princess Diana

When it comes to fall dressing, no one has yet to do 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, mom 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 no doubt note 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 crewneck, acid wash jeans, a plaid blazer, and the same cap and boots. 

With the fifth season of The Crown having just come out on Netflix, Diana-inspired looks are bound to be even more popular than usual this fall. Follow EmRata’s lead by recreating the two iconic outfits below all season long. 

WHO: Princess Diana

WHO: Princess Diana

When in doubt, go for the authentic pair. 

The old-school look is always cool. 

Everyone at Who What Wear is obsessed with these.

Need.

These are beyond chic. 

Okay, luxe. 

These look just like Diana’s.

Back2back champs. 

Just do it.

Every fashion girl’s favorite brand now makes baseball caps.

Goals.

What’s stopping you?

Diana blue. 

Need.

These are selling out lightning quick.

Perfect for greasy hair days. 

*Adds to cart.* 

Oh, you need this one. 

I have a pair of Ganni cowboy boots and yes, they’re worth the price.

Next up: EmRata Wore a $40 Zara Skort With the Boots on Every Editor’s Fall Wish List