Preppy style is always in, but I love when it trends in a bigger way within the fashion space. Lately, I’ve really been feeling a resurgence of preppy, Americana-inspired brands like Polo Ralph Lauren, L.L.Bean, and Gap, which all point to preppy style being at the forefront of the industry once again. We’re also seeing some newer players in the preppy space, such as Alex Mill and, of course, Tuckernuck, who have each brought their own twist to this classic aesthetic.
With this renewed popularity, I thought it would be fun to put together a complete guide to preppy style. Today, I’m going to break down how I define this aesthetic, how to achieve it in 2026, my current favorite pieces, and, of course, a few preppy outfits.
How I Define Preppy Style
Preppy style is a broad term that can mean something different from person to person. For me, prep is all about classic, timeless styles that feel polished, with a slightly sporty edge at times. It’s about looking put-together yet effortless — never overdone.
Preppy Patterns, Fabrics, & Colors
Similar to quiet luxury or old money style, achieving a preppy look is less about logos and more about selecting the right fit, fabric, and overall styling. When it comes to prints and patterns, there are a few tried-and-true options you’ll often find in preppy outfits. Classic stripes and plaids are always an easy go-to.
There are also certain fabrics that lean preppy, such as utility-inspired materials and madras. And when it comes to color, preppy outfits typically revolve around a primary color palette or soft pastels.
How to Dress Preppy in 2026
Preppy style has remained fairly consistent over the decades, but there are always subtle shifts and trends within the aesthetic as time passes. With old money style, Carolyn Bessette-Kennedy dressing, and minimalism all currently top of mind, preppy style in 2026 leans more toward subtle, refined nods rather than anything too overt.
I’d compare 2026 preppy outfits to a more toned-down version of what we saw in the early 2000s — let’s say around 2006. It’s no longer about stacking two polos or layering multiple plaids and stripes in a single look. Instead, this aesthetic today feels more streamlined, refined, and understated.
A Guide to a Preppy Style Wardrobe: 6 Staple Pieces
Now let’s walk through some of the styles that I feel really anchor a preppy look. These six pieces are must-haves when it comes to building a preppy wardrobe. And the best part is, once you have them, you can easily mix and match them with other pieces to create endless outfit combinations.
1. A Canvas Tote
Starting with an accessory, a canvas tote is a cornerstone of a preppy wardrobe. The Boat Tote is trending again in a big way, and we’re now seeing brands put their own spin on this classic — like this standout bag from Alex Mill. The shape, size, and function are practical and perfect for everyday summer outfits.
A modern update to this timeless bag comes in the form of cheeky embroidered slogans or, in Alex Mill’s case, an updated, hand-painted monogram. Another great option? This cotton canvas weekender in two very preppy hues.
2. A Great Cardigan
Cardigans are no longer just for your grandmother. While your initial thought might be a stuffy sweater set, the cardi feels fresh — and even a bit sexy — again in 2026.
Some of the coolest takes on cardigans right now include ribbed styles (which look perfectly chic worn on their own), sheer options,elongated silhouettes, and this very cool roll-neck cardi. However, if you prefer to keep things more classic, my two personal favorites are this cardigan and this one.
3. An Easy Drawstring Pant
The drawstring pant has to be the pant of the summer. It’s relaxed and comes in oh-so-many materials, ranging from classic linen and poplin to more unexpected options like taffeta. I talked quite a bit about how this style has taken the internet by storm in this post.
While that particular pair appears to be sold out everywhere, there are plenty of alternatives at much more approachable price points. If you’re into linen, I highly suggest this drawstring pant or this one. Prefer poplin? Try these pants or this style. And if you’re looking for a little more zing, this version comes in stripes,gingham, or even a very cool pom-pom fabric.
You can create so many preppy outfits with any of these pants. Simply pair them with a classic tee, a pointelle tee, or a relaxed button-down.
4. A Great Third Piece
Since preppy outfits were practically made for places like Nantucket or Martha’s Vineyard, it only makes sense you’d need a great third piece or a lightweight sweater for when the temperatures dip and the fog rolls in at night.
Something like this utility jacket in an interesting color or an incredibly timeless bomber jacket would do the trick. A trench is another great option, and the fit on this one is 10/10.
5. Simple Sandals & Ballet Flats
While you might argue that boat shoes or smoking slippers feel far preppier than simple sandals or ballet flats, in 2026 the latter feel more relevant and modern.
As you already know, when it comes to flats, I’m a huge fan of all things Margaux, including these and these. They’re incredibly comfortable, beautifully made, and hold up so well over time. As for simple sandals, my current go-tos are these and these.
6. A Classic Shift Dress
A simple shift dress is the preppy dress of summer. Not too short and not too tight, it just feels like a relaxed yet polished moment.
This dress is damn near perfect, and if denim is your thing, this shift is not to be missed. A great alternative to a woven version would be a knit, striped option, such as this one, which is on sale right now!
Preppy Outfits to Recreate
Now let’s have some fun and put together a few preppy outfits for spring and summer! Keep in mind, the goal is to look classic, elevated, and put-together while still keeping things fairly minimal and streamlined. Here are a few ideas for different upcoming occasions.
Preppy Graduation Look
The end of spring and beginning of summer marks grad season. I’ve gotten quite a few DMs asking what to wear to a graduation as a guest, and leaning into preppy style is the perfect approach for this type of event.
Most likely, the graduation you’re attending will be outdoors — and hot. For this reason, I’d opt for a classic shift dress that feels dressy but not over the top. Add these comfortable sandals (since you’ll likely be walking through grass and possibly covering a fair distance), and don’t forget a great pair of sunnies — these are perfect for this look.
I’d also recommend throwing this sweater over your shoulders. Not only does it add interest, but it will also keep you comfortable if you end up inside in chilly AC after the ceremony.
A Day on the Water
I love a good boat day, and I also love the preppy outfits that come along with it. One of my favorite looks is pairing longer-length shorts (such as this under-$30 style) with a great button-down and a clean pair of sneakers. A pair of aviators finishes the look perfectly.
This is where the boat tote really shines — both in its preppiness and practicality. Another great finishing touch for a day in the sun is a non-logo baseball hat. I’m currently loving this one from Chord.
Sunday Morning Coffee Run
Lastly, let’s put together an easy yet chic look for a morning coffee run. This cable-knit polo screams prep, so I’d pair it with a more contemporary preppy piece like these drawstring pants and a pair of Adidas sneakers. If it’s chilly, I’d also add socks and this adorable barn coat I’ve been eyeing. To finish the look, the Alex Mill monogram tote would be absolutely perfect!
A Modern Take on Preppy Style
Whether you’re like me and have always loved preppy style or you’re simply looking to dip your toes into it as its popularity continues to grow, I hope this guide is helpful. Spring and summer are the perfect seasons to reach for classic, timeless pieces, and there are so many fun ways to put a modern 2026 spin on the look. It’s a style that will never go out of fashion.
For more timeless outfit inspiration, be sure to check out these posts:
How to Master Old Money Style: 10 Classic Pieces + Tips
What to Wear to a Graduation: How to Dress as a Guest
How to Create a Classic Fashion Wardrobe: Timeless Style Tips
10 Spring Clothing Essentials & How to Style Each
