The Ultimate Guide on How to De-Prep Your Preppy Fashion Staples

How to easily turn your vests, riding boots and other preppy pieces into cool, modern, and fashion-forward fits.
Author:
Publish date:

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.

The Polo

polo-shirt-color-blocking

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! 

A Nautical Blazer

nautical-blazer-preppy

Products: Blazer - Macy's, Tee - UO, Cutoffs - Revolve, Booties - Steve Madden, Socks - Target, Crossbody - Forever 21

For this look, I decided to match a navy nautical blazer with an opposite piece of clothing for a cool-girl aesthetic. What did I choose for my opposite piece? A pair of cut-offs! Name a better duo.

This article outlines how to look "like a model off duty," and look number six shows a blazer matched with a pair of cut-offs as well but paired with tights and Doc Martens. The entire article highlights the incredibly, seemingly effortless, chill-girl look that models seem to have down easy.

The cut-offs in this look are AGOLDE which are more on the expensive side,  but worth every penny. I have a pair of AGOLDE jeans that I love and they are very high quality in make and fit. 

Colorful Cropped Pant

color-pants

Products: Tee - H&M, Peplum Tank - UO, Pants - Express, Espadrilles - Zappos, Earrings - Forever 21

I chose to use alternative layering to make these yellow pants look fun and more fashion-forward. To start, the white tee is worn under the denim peplum top. The plain primary colors between the pant, denim top and earrings give off an artistic feel. The lilac espadrilles are close in color to Pantone's color of the year for 2018, ultraviolet

I have a pair of yellow pants I got at a consignment shop and could never figure out how to wear. I ended up doing something very similar to this look:

me wearing pants

Me, just trying to figure out how to wear these patterned, yellow pants that I questionably bought despite my distaste for J.Crew. 

As you can see, I also mixed patterns. (Read my article about how to mix patterns for more info.) This is another way to deconstruct a preppy find and make it more modern. I did that below as well using the same checked print in different sizes and colors. 

Leandra Medine, my biggest muse and creator of Man Repeller, wrote an amazing article about mix matching prints using preppy green polka-dotted pants as an example. Here's another look that riffs on this idea:

color-pants-2

Products: Sweater - Zara, Pants - Banana Republic, Clogs - Forever 21

The Puffer Vest

vest-outfit-preppy

Products: Vest - Macy's, Hoodie - UO, Button-Down - AEO, Jeans - Gap, Doc Martens - Nordstrom

For this outfit, I found a very basic black puffer vest and worked hard to spin a somewhat edgier look out of it. The fringe of the two-tone jeans, the black Doc Martens, and the cropped hoodie over a crisp white button-down mimics the cool-girl style we attempted with the navy blazer above. This outfit downplays the preppiness that a vest can give off, and makes it more utilitarian. 

This outfit would work well in the ever-changing temperatures of my campus, for sure. With this many layers, you'd have many options of warmth throughout the day from inside to outside. 

What do you think?

Do you like the way I re-imagined some of these preppy pieces? Let me know in the comments. Be sure to tag @collegefashion in any outfit photos if you try this -- we may feature you on our Instagram!

Related Stories