Princess Diana's impact extends far beyond her impeccable sense of style. Today, we are reminded of her timeless fashion choices ahead of their time, and they continue to inspire us, especially for the fall season. From cowboy boots, college sweatshirts, and biker shorts to daily workwear and iconic luxury bags named in her honor, Diana effortlessly embraced trends still relevant today for the working consumer.

Fashion repeats itself, and Diana's iconic looks deserve to be recreated. She was a trailblazer, leaving a lasting legacy influencing the fashion world for women to add to their wardrobes. Let us honor her by embracing her style with these must-have looks to recreate immediately!

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For a classic little black dress paired with tights and simple black pumps for an all-black look that amplifies any evening event, it can be Aritzia’s Bond mini dress. You can’t forget this lovely blazer from Rag & Bone to match Banana Republic’s Arden suede pump, or you could even do their low-heel mule. A handbag alternative to the Lady Dior can be Teddy Blake’s “Kim Stampatto” 11” black bag or Tory Burch’s “Eleanor” satchel bag that mimics the Dior perfectly.

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Diana always rocked her specialty blazers that always came in handy with any workwear look or a daily errand run. You can be more experimental with Tuckernut’s houndstooth wool tweed “Kensington” blazer that can be paired easily with their suede “Velma” boots. Girls love their caps, so Anthropologie’s “Wanderlust” cap is an excellent addition to this outfit.

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There is nothing like wearing prideful colors, especially with any gym outfit, which can be Athleta’s ultra high-rise biker shorts and matched with any sweatshirt you choose, like Good American’s “New York.” For that awe-inspiring Americana look, SunKissedCoconut’s vintage sweatshirt is perfect. Large carryalls are essential gym bags, but if you're looking for something more stylish, this leather Marc Jacobs tote or Freja New York’s “Linea” tote is great.

New Balance’s 327 sneakers or the 990v6 “Grey” are a great alternative for the sneaker option.


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Varsity jackets are very retro and can be used for any look, like Varsity Base’s letterman jacket with the iconic red and black colorway, a complete dupe of Diana’s, as seen in the picture. This look can be paired with any boots, but ETRO’s “Cavalry” boots are a great color for this Abercrombie & Fitch ‘90s dark-wash slim jeans.

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Diana effortlessly mastered the art of achieving a sophisticated yet relaxed workwear look. Who said you couldn’t wear monochromatic looks in the fall or all blue, even if it’s cold? This simple and feminine Everlane relaxed light blue oxford is great for any working day and can be paired with White House Black Market’s “Elle” trousers and M.Gemi’s “Esatto” flats.

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Another round with the varsity looks would be this sportswear jacket by Roots, a Canadian brand whose camp-like, wilderness aesthetic. Their vintage varsity jacket encapsulates well with maybe or maybe not this midi skirt from Zara and Everlane’s crew shirt to capture this late afternoon Diana look.

Princess Diana effortlessly pioneered the bike shorts and oversized sweatshirt combo trend, almost as if she had created it herself without realizing. She flawlessly embodied the model-off-duty look long before it became popular, and “quiet luxury” was uniform but never considered a trend. Winter is right around the corner, and these looks are perfect before it gets too cold to wear!

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