Inside: Cute and preppy outfits for all of your aesthetic needs.

Preppy outfits are back! Now stronger than ever, but the word preppy means something a little different now than it did back in 2015.

The prep school vibe aesthetic comes and goes every few years, because it’s a classic. But this time around, it’s actually an aesthetic that I’m a big fan of and have had a lot of fun creating outfits with. It’s not the same business casual vibe we were getting around eight years back, but instead it’s a reflection of some of our favorite old money TV characters from Gossip Girl.

We’re seeing a lot of tailored pieces being brought into our casual attire as well as loafers and button downs. They can all be styled so many ways that it only makes sense that they’re doing so well! Versatile pieces that also give you an elevated and wealthy look about you are pieces that I plan to keep in my closet for a long time, personally.

So if you’re wondering how you can hop on the preppy train and not look like you just walked out of a business meeting into a work happy hour, then these are some of my favorite outfit ideas for you!

It’s all about styling, so let’s look at these pieces, how they fit, and how they’re styled together.

Four outfits that are classy and preppy.

Is Preppy Still In Style?

In short, yes!

I’ve touched on this a bit already, but the preppy look is so classic, it comes back every few years to give us a new version of it and make us remember why it makes its rotations.

Preppy in the statement necklace and sock bun style is not still the move. The funky business casual isn’t quite what we have in mind when we talk about preppy in 2023. And we’re not talking about southern sorority rush, either.

We’re talking mini skirt school uniforms and cool oversized blazers. We’re talking ruffled dresses that are perfect for spending the summer in the Hamptons. We’re talking about classy bows, pleats, and flowing fabrics.

There’s a very specific kind of preppy that is in style, and you’ll see what I’m talking about here in this post.

Styling For The Different Kinds

There are some pieces that can be styled differently, and if there’s anything I could say about how to style them differently, it’s all in the jewelry and all in the shoes.

Jewelry that you’ll want to avoid is anything large. Oversized beaded earrings and chunky necklaces are cool and cute, but they’re more of the southern funky preppy than they are the classy East Coast kind of preppy.

What you’ll want to look for instead is the dainty chain necklaces, the pearl earrings, the vintage looking pendants. With old school preppy, less is more. Let the little pieces speak loud.

The shoes are more versatile, but a classic white sneaker and a flat and simple sandal will take you places. Avoid cowboy boots, though trendy, unless it makes the outfit cool in a mega trendy and chic way instead of the southern and western way.

Either way this can be styled is going to be so cute, we love all kinds of preppy here. But the East Coast is greater than the south in hot fashion trends right now, so play your cards right between the two different styles and you’ll be more on trend than ever before!

Four outfits with button downs and sweaters

Preppy Outfits

1. Classic Sweater
2. Strong Shoulder
3. Frilly Blouses
4. Blue Button-down
5. Knit And Silk
6. Clean Look
7. Casual Tennis Team

What Are Preppy Aesthetic Colors?

There are several factors to what makes something “preppy.”

While a color won’t make or break whether an outfit is truly giving the preppy vibe or not, it definitely makes a difference in which style of preppy it’s giving.

Neutrals are always a perfect and safe route to go when it comes to your preppy outfits, but specifically the classics like black and white. And add in some navy, and you’ve got your solid foundation of colors for a preppy outfit.

Building on that, your light blues, royal blues, soft natural green, and kelly green are going to be your preppy color palette. There’s nothing classier and more classic than the blues and greens colors. Navy and white will forever be the preppy classic.

Any color can work in the preppy color palette, especially when it comes to events and cocktail and formal dressing, but people that usually fit in this category for real know the correct colors for the current seasons.

If the cut of the dress works for the overall aesthetic, the color will too. But remember that less is more, so being too loud with your colors can take away from the aesthetic in general.

A girl in Europe wearing a white oversized sweater

Prep Trendy

8. Classic
9. The Basics
10. Cool Knit Sweater
11. Houndstooth Patterns
12. Button Down Sweater
13. Puff Sleeve Shirt Dress
14. Tweed Outfit

Why Is It Called Preppy?

If you’re wondering why it’s called preppy, you’re in good company. There’s plenty of people who use the term and description without really knowing where the label came from.

Preppy simply refers to the style that naturally evolved from the generally upper class schools called “university preparatory schools,” that prepared middle and highschool students for higher education. They’re more common for the upper class because of the cost of tuition of these schools, and they’re usually geared towards helping their students get into more elite universities like the Ivy Leagues.

Of course this is the kind of school that the characters in Gossip Girl attend, the show that usually sets off each round of preppy trends and a rising popularity in the kind of attire that they wear in the show. When the show hits the trending charts again, though having been off the air for years now, it generally creates a spike in this style.

While there are preparatory schools all over the United States, these are significantly more popular and renowned on the East Coast, where a majority of the Ivy League schools are also located.

This is where the term preppy comes from, and why it’s so specific to a certain demographic like old money on the East Coast.

Whatever they’re wearing, we’re wearing.

Three classy and beautiful preppy outfits.


15. Classy Cuts
16. Blue And Whites
17. Classic Layers
18. Paris Dress
19. Blazer Set
20. Casual Layers
21. Sweater And Shorts

Preppy attire is the epitome of classy and elegant. I have always had a little bit of hippie in me personally, but there are still some really cool ways to make preppy and hippie work together, even though they’re pretty opposite, and simply make the free spirited hippie girl inside of me more of a classy and elegant moment. But still be a little free.

It’s not stuffy, it’s not what you picture your grandmother wearing. It’s a lovely and incredibly popular trend right now, and there are always ways to incorporate it into your personal style without totally changing your aesthetic if it’s a trend you simply plan to follow while it’s a popular thing.

Some events and occasions really do call for it specifically, as it’s a fairly appropriate vibe for school functions, work meetings, or some events in general.

However you plan to dress preppy, I hope these outfit ideas gave you the perfect amount of inspiration!

If you plan to rock the green from the color list, here’s a guide to green shorts outfits– perfect for the summer or late fall outfits that need a little pop of color.

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