How to Recreate Princess Diana’s Best Outfits

Oversized sweatshirt

What is it about Princess Diana’s style? An uncanny relevancy decades later? A perfect cocktail of aesthetic intrigue and practicality? A mesmerizing twist on classics that might otherwise be considered stuffy or stale? I’m inclined to think the answer touches on all of the above. In honor of the uptick in visibility bestowed upon Princess Di’s fashion icon status courtesy of Instagram’s ever-churning nostalgia machine, I challenged Man Repeller contributor Juliana Salazar to reinterpret her best outfits for 2019. Below, the very inspiring results.

Outfit #1: A De-Puffed Polka

A puffy-sleeved polka dot blouse tucked into a pencil skirt (which you can see in full here) and cinched with an oversized belt looks decidedly charming on Diana, but might seem a bit dated if replicated exactly now. Juliana gave the get-up a modern update with a pair of white Bermuda shorts from Markoo, a blouse with significantly less puff from Aritzia, and a belt that contrasted instead of perfectly coordinating.

Outfit #2: An Iconic Sweatshirt

As excited as Juliana was to recreate this (admittedly legendary) look, she was even more excited to discover that you can purchase a replica of her exact sweater online for just $30 (pro tip: size up to achieve optimal bagginess). To adapt the ensemble for the modern age–not to mention for life outside the gym–Juliana swapped Diana’s large messenger bag for a tiny shoulder bag from Gimaguas, and her white sneakers for gray New Balances.

Outfit #3: An Ideal Approach to Rainy Day Errands

After attempting her approximation, Juliana deemed this “the ideal outfit for a rainy/ugly day when you have a bunch of running around to do,” and I’d have to agree. She pointed out that the casual nature of the hero pieces are counterbalanced by the obvious intention imbued by matching your sweatpants to your sweatshirt and polishing it off with a tailored blazer. Patent leather cowboy boots give the original ensemble a slightly glossier spin.

It’s worth doubling down here, in the final sentences of this royal style opus, on how refreshingly simple these outfit combinations are. They are largely composed of things you probably already have in your closet: a patterned blouse, white shorts, a sweatshirt and sweatpants, a baseball cap, etc. And perhaps that’s what makes Princess Diana’s outfits so compelling: She could have worn anything she wanted, and her outfits could have easily skewed inaccessible as a result, but instead she gave us the gift of accessibility interpreted through the $free.99 lens of personal style.

What are your favorite Princess Di looks? Have you ever tried copying one of them? What did you eat for breakfast this morning? (Unrelated, but inquiring minds want to know).

Photographed by Louisiana Gelpi and styled by Juliana Salazar.

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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