Princess Diana's Sporty Outfits Still Feel On Trend Today

She’ll inspire you to wear varsity jackets.

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Princess Diana wearing a varsity jacket at Alton Towers Theme Park.

Princess Diana has become an emblematic style figure for making sportswear feel polished. In fact, many of Princess Diana’s sporty outfits are ingrained into one’s psyche. For example, if you spot someone wearing biker shorts with an oversized crewneck, it’s possible to view the combination as a reference to one of her signature off-duty looks. (Throw in a pair of white tube socks and chunky dad sneakers, and the ensemble then becomes a carbon copy of Princess Di’s iconic biker shorts outfit.) Similarly, before French fashion house Celine revived the baseball cap and blazer combo — the late royal rocked the look circa 1988.

Many of her archival sporty outfits reflect the trends of today, too. The royal loved collegiate wear — in particular, varsity jackets and oversized blazers — which have both become key components of 2021’s preppy style resurgence. And long before you ever had a desire to wear matching loungewear separates, Princess Diana would throw on a coordinated tracksuit with some white tennis shoes. This was her choice of outfit for running errands in.

Ahead, TZR combed through the late royal’s style file to find her most memorable sports-inspired ensembles. You’ll be able to shop similar pieces to her looks, too, so you can easily recreate any of her outfits.

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The Iconic Biker Shorts Outfit

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Her iconic biker shorts outfit has a fashionable legacy, so much so that Hailey Bieber once recreated the look for a Vogue Paris photo shoot. Princess Di’s outfit, pictured above in 1995, still feels relevant today because the look was composed of everlasting wardrobe staples: a navy crewneck top, biker shorts, tube socks, and white sneakers.

A Varsity Jacket With A Tailored Skirt

Jayne Fincher/Princess Diana Archive/Getty Images

If you study Princess Diana’s sporty outfits with a careful eye, you’ll observe a common theme. Oftentimes, she’d wear an unexpected combination of pieces, items that you likely never expect to work together but inexplicably do. Case in point: her varsity jacket and pencil skirt pairing. The letterman jacket is not an obvious choice to go with her tailored bottom, but, again, her outfit tapped into that casual-meets-polished essence she was famous for.

A Black Nylon Tracksuit

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An age-old trick that adds refinement to any ensemble is to wear coordinating black separates. Here, Princess Diana ingeniously applied the style hack to a tracksuit, thereby portraying the nylon set in a way that evokes more fashionable gravitas. Daily Paper offers a black and blue set that embodies the royal’s noir look. Plus, the buzzy brand’s tracksuit references today’s color-blocking trend, so it’s a profoundly relevant pick.

A Baseball Cap With A Blazer

Terry Fincher/Princess Diana Archive/Getty Images

To take a business casual look such as a blazer and jeans combo into the weekend, simply top your outfit off with a sporty baseball cap. Here, the late royal wore the laid-back, but polished look to the Guards Polo Club in 1988. Some 30 plus years later, Princess Di’s whole outfit still feels on trend if worn today.

A Ski Outfit For On & Off The Slopes

Jayne Fincher/Princess Diana Archive/Getty Images

The late princess was an avid skier. To harness her slopes-inspired spirit, wear a utilitarian puffer jacket with a pair of sleek black leggings. Of course, you can also opt for outerwear that takes a more glamorous approach to alpine fashion — like Miu Miu’s lilac quilted puffer. (The fur-collared jacket debuted during the fashion house’s Fall/Winter 2021 show, which paid an homage to skiwear.)