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How I'm Incorporating The Preppy Trend Into My Fall Wardrobe

Princess Diana is the blueprint.

Tim Graham/Tim Graham Photo Library/Getty Images
HIGHGROVE, UNITED KINGDOM - JULY 18:  Prince Harry And Princess Diana In The Grounds At Highgrove Wi...

When it comes to trends, what goes around truly does come around. That’s definitely the case with this fall’s preppy trend. The Gossip Girl reboot is partially responsible, but thankfully, the show is giving this trend a much-needed update. Penny loafers are being replaced by their chunky-soled counterparts, school uniform skirts are getting the high-waisted treatment, and sweater vests are undergoing a playful update. I’m ready to take this trend head-on for fall and share how I’m styling these pieces along the way.

When pulling looks I wanted to try and emulate this season, I started from the top of my list of inspirations: Princess Diana. Princess Diana’s style was effortlessly classic. When it comes to defining her style, it’s impossible to put her in just one category, especially as her looks evolved over time, but elements of Lady Di’s wardrobe definitely fall under preppy. A few of the elements I’ll be including in my fall outfits courtesy of Princess Diana include styling ideas — sweaters wrapped around my shoulder or waist, or layered over button-downs — and specific purchases as well — straight-legged white jeans and loafers. Labucq’s Kitty Loafers will definitely get the job done on that last point.

Princess Diana Archive/Hulton Royals Collection/Getty Images
Princess Diana Archive/Hulton Royals Collection/Getty Images

But, Princess Di isn’t my only source of inspiration for this trend, my Connecticut upbringing means I was born ready to take it on. I wholeheartedly objected to pastels, Lilly Pulitzer, and pearl earrings as a child (sorry Mom and Dad, I’m a stubborn Pisces), and I’ve never swung a golf club, but resurrecting tennis dressing has been on my mind lately. The tennis skort gained massive popularity this summer, especially over on TikTok. While skirts are definitely more of a summer item, I’ve found some super stylish ways to keep this trend going well into fall.

All in all, I’m super excited to experiment with preppy dressing this season. Ahead, check out the preppy pieces I’m incorporating into my fall wardrobe.

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Chunky Sweaters‌

Layering weather is upon us, and the only kind of layer I want to do is chunky knits on top of crisp button-downs. My favorite way to pull off this trend is with an oversized sweater that has a roomier fit.

Tennis Skirts

I plan to wear my tennis skirts all season long by pairing them with a chunky sweater up top (or drape that sweater over my shoulders on days when it still feels like summer). Once things cool down, I can always add tights for an additional preppy touch.

White Straight Leg Jeans

That old “no white after Labor Day” rule is SO outdated, am I right? White denim goes especially well with neutral-hued blazers or sweaters, so I’m looking forward to layering up.

Sweater Vests

Sweater vests can be worn on their own, or atop dresses and shirts, the possibilities are endless. Personally, I prefer a sweater vest in a fun pop of color or print to add a playful touch to my look.


My secret weapon: I always pull a look together with a pair of loafers. Layer with tube socks for the ultimate preppy outfit (extra points if your socks have a lace ruffle).