Preppy School-Girl Shoes Are Trending—17 Pairs to Help You Catch the Vibe

Whether you went to preppy private school or not, there were certain pairs of shoes that still to this day you immediately associate with elementary and high-school uniforms. The shoes I am referring to include Mary Janes, T-bar shoes, brogues, oxfords, and a few iconic others. It seems that fashion girls have taken a particular liking to these nostalgic shoe trends this season and naturally, the ways they have been styling said shoes are legendary in and of itself. 

Ahead, I have rounded up my personal favorite pairs of preppy school girl shoes that are both practical and stylish and included some inspiring Instagram imagery along the way. You'll notice that when it comes to nailing this fall shoe trend, white ankle socks, pleated miniskirts, and a few other key pieces are a must, so keep scrolling to find out more. 


(Image credit: @ada_oguntodu)

This preppy shoe trend is not styled in any way that you're used to. Take this casual athleisure look as a perfect example. 


(Image credit: @alyssainthecity)

Lean into this prep-school movement by way of pleated miniskirts, ankle socks, and the shoes to match. 


(Image credit: @sofiamcoelho)

Surely you'll see a few pairs of shoe in here that you literally wore back in the day, but there are also some fresh updates to the classics you're used to like these extra-chunky soles. 


(Image credit: @shhtephs)

Can you ever really go wrong with shoes from Dr. Martens? No, you can't. 


(Image credit: @champagnemani)

From the cardigan to the miniskirt to the classic shoes, this look is perfection. 


(Image credit: @stephaniebroek)

In case you haven't noticed, it's the stark-white ankle socks that really help these preppy school-girl shoes pop. 


(Image credit: @ada_oguntodu)

Update your favorite pair of denim with this striking shoe trend. Once again, little white socks make all the difference. 


(Image credit: @alyssainthecity)

It doesn't get much simpler or much cuter than this look. 

Editorial Director

Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over eight years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Kaia Gerber, Normani, and Kristen Stewart.

She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her personal style has been featured on sites such as Vogue, Harpers Bazaar, and Elle. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.