Everyone goes through their Lilly Pulitzer, Vineyard Vines phase — it’s practically a rite of passage for women our age. Later, however, many of us find ourselves embracing an entirely opposite style direction. Some people love preppy style for life, and if that’s you, more power to you! But if you’ve moved on from your preppy phase and you’re wondering what to do with all those clothes, this is the article for you. 

You don’t have to throw out all your prepster clothing once you’ve decided to reinvent yourself in a more fashion-forward way; just style your pieces differently and make them work for today! And yes, it is possible to turn even a colorful pair of Bermuda shorts into something super cool and stylish.

Below are the top four most preppy clothing items I could think of and ways you can still wear them, even when you have moved beyond preppy style.

Table of Contents

The Polo

Products: Polo – Macy’s, Midi Skirt – H&M, Sneakers – DSW, Bracelets – ASOS, Sunglasses – UO

This monochromatic outfit is modern and chic. This bright pink Lacoste polo is preppy as preppy gets, real Cady Heron vibes, but paired with this red midi skirt looks minimalistic and cool. Pop the collar of the polo, keep it completely unbuttoned, and tuck it into the skirt. 

Continuing with the color coordination, pair these pieces with bright red Puma sneaks. Why wear anything but comfy sneakers when you can make them look so fashion-forward, right? For some extra fashionista points, I added a pair of super trendy retro sunnies. The black offsets all the color and yet still looks super cute and playful like the rest of this exciting look. 

Who knew you could pair a pink polo shirt with anything else but a golf skirt? 

You can go in many directions with a short sleeved polo, too. This blogger donned her polo completely buttoned up for a serious ’70s throwback. She matched her vintage-looking polo with a leopard mini skirt and sport-y slides. There are so many styling options!