Olivia Ponton Elevates Academic Chic in Pleated Skirt at NYFW

Who says preppy fashion should only stay in the classroom?

Olivia Ponton attends the US Open Tennis Championship in New York City in September 2025. / John Nacion/Getty Images

Olivia Ponton is bringing classroom couture to the streets of New York, proving that the preppy aesthetic is a timeless style that can be worn on almost any occasion.

All eyes were on the two-time Sports Illustrated Swimsuit model as she strutted her stuff on the sidewalk in time for New York Fashion Week, wearing a stylish top and skirt.

Olivia Ponton goes preppy in New York City

Olivia Ponton attends the Tory Burch fashion show in New York City in September 2025. / Aeon/GC Images/Getty Images

Her white button-up long-sleeve shirt has white rings hanging on the hem. The embellishment helps make the top more than just an average button-up, making her stand out even more. The same sentiment goes for the khaki mini skirt. The pleated bottom scores easy fashion points from us.

Tying everything together, Ponton sported a pair of white shoes with a peek-a-boo cut placed in the front. To match both her top and shoes, she opted for a white purse with a buckle strap. From head to toe, she looked fabulous.

Olivia Ponton attends the Tory Burch fashion show in New York City in September 2025. / Dimitrios Kambouris/Getty Images for Tory Burch

Ponton shared a gorgeous slow-mo video of her look on Instagram, writing in the caption, “Arrivals @toryburch.”

Ponton has remained booked and busy this summer with various trips, events and jobs. There’s no doubt we’ll continue to see her in big-name campaigns, most recently starring in features for Victoria’s Secret PINK.

A day in the life of Ponton

As per her latest YouTube vlog, the day in the life of a model is very fast-paced. Ponton took her audience on a behind the scenes tour of her VS PINK campaign, showcasing how quickly she goes from a chill morning with a match latte in hand and Ransom Canyon playing on her TV to sitting in a trailer getting her hair and makeup done.

She unwinds from her busy day with some relaxing time in the bathroom and some reading. Though after some brief shut-eye, she’s right back on set, ready to deliver once again.

Ponton also chronicled a fitting for a Halloween-themed VS Pink campaign. This one required her to wear various costumes, such as a cat and a bunny. An easy favorite has to be any look featuring a jet black wig, as it’s a nice shake-up from her blond tresses. She named this alternate version of herself Roxanne or “Roxy.”

Once she wrapped this job, the model was already on her way to her next location. The hustle and bustle of Ponton’s modeling life is quite impressive, speaking to her hard work and passion.

Here’s to hoping her next YouTube vlog details the ins and outs of New York Fashion Week—including this awesome preppy look.

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