How to Dress Preppy
Preppy style is classic and sophisticated. It’s a style personality that men and women can wear and look great doing so. Whether you’ve always been drawn to preppy style or you’re hoping to embrace it into your wardrobe more there are plenty of ways to dress preppy. In fact, you may already own pieces that can be styled to encompass the preppy style to create outfits uniquely you.
If you’re need a boost of style inspiration you’re in the right place. Check out some of our favorite preppy outfits for guys and girl and enjoy reviving your preppy style.
1Casual Sweater Prep
Preppy style is often associated with more formal dressing. That being said, you can incorporate preppy aesthetic into casual wear also! Jeans, flats and a sweater get a preppy twist in this outfit. The striped detail at the neckline of the sweater takes the sweater from a basic to prep staple.
2Preppy School Girl Vibe
There’s something about a skirt and blouse that we’ll never get enough of for the ladies. Pairing an a-line skirt with a white blouse is timeless, the black bow at the neck adds that extra preppy touch we love. Keep the other pieces neutral to allow the skirt and blouse to stand out.
3Classic Men’s Business Casual
Guys, don’t underestimate the power of a classic look. This color combination is the epitome of classic in menswear. We love the combination of casual pieces with formal for the perfect business casual vibe. Khaki pants are instantly elevated to embrace a preppy style with a blazer and white shirt.
4Dressed Up Cardigan
Don’t get it twisted, cardigans can be dressed up guys! This look is a great example of that. Striped shirt, tie and classic pants are a great combination for preppy style. The cardigan adds even more of a preppy touch.
Many of us associate preppy style with an All-American vibe, which is exactly why this look is the essence of preppy style for men. The American flag sweater completes this casual outfit. We love the monochromatic blue shades, too.
6Men’s Spring Prep
As the weather gets warmer with spring (quickly) approaching, use this outfit as inspiration for a preppy casual option. Ivory denim is a great alternative to traditional blue jeans and when they are paired with a light colored collared shirt it’s an easy outfit that looks even better.
7Preppy Style Turned Chic
Ok, seriously…how chic is this look? The blazer is timeless with a preppy flair all its own. But it’s the details of this look that really take it to a new level. The headband, big sunnies and unique buttons on the jacket are giving us all the preppy feels.
8Go-To Casual Prep
Add a preppy edge to your favorite casual look by adding a vest. Khaki pants and a plaid collared shirt get a whole new look with one simple addition. Not to mention, vests are a great piece for the transition from winter to spring.
9Accessorized for Prep
We are totally obsessed with this preppy outfit. Isn’t it perfect for spring? The light color palette is fresh and easy to wear. The foundation of this outfit is fairly simple, striped shirt and white jeans. But this is a great example of how just a few accessories can add a unique twist. Tying a sweater around your shoulders is a staple for preppy style, not to mention it’s effortless!
We can’t help but think of the Hamptons when we envision preppy style. This outfit is the perfect example. Even if you’re not in the Hamptons you can recreate this pastel toned outfit to achieve a similar preppy look.
11Over the Knee Touch
This outfit is giving us major Gossip Girl nostalgia. In a good way, of course! Style a plaid dress with a peacoat for a comfortable preppy outfit, but instead of keeping the shoes simple compliment the plaid with over the knee socks and matching booties. The over the knee socks really take this look up a notch, don’t you think?
12Classic Women’s Preppy Vibe
When we picture a classic preppy outfit for women, this is definitely what we envision. Preppy style is really all about classic, tailored pieces paired together. Mixing textures like suede boots and a plaid jacket complete the vibe and make the outfit more unique.
13Mixed Prints with a Preppy Touch
Mixing prints is a great way to style an outfit that is uniquely you. We adore this plaid cape already, and when paired with a striped shirt it’s even more chic. The perfect outfit to keep it casual while representing a preppy personal style.
14Layered Plaid Dress
White shirts are definitely a go-to staple if you enjoy preppy style. Not to mention, they’re insanely versatile. Give your plaid dress a makeover by layering a simple white blouse UNDER the dress. Such a simple style hack that looks amazing.
15Suit Separate Classic
Suits are (obviously) a must have for every guy’s wardrobe. One way to make your suiting more versatile is to mix and match to wear them was separates. Tan and navy are a timeless color combination, it’s perfectly complimented with the gingham shirt. The boat shoes add a subtle preppy touch.
16Chic Preppy Cardigan
One of the great things about preppy style is the simplicity of it. Even though this is a fairly simple cardigan it feels anything but boring worn this way. Keeping a cardigan buttoned allows you to wear it more like a shirt giving it new life.
17Updated Preppy Suit
This blazer gave us major Ivy League vibes, which is truly the essence of preppy style. A classic blazer gains more personality with the addition of a crest design on it. Pair it with a striped collared shirt, tie and matching pants for a suit look that’s sure to stand out.
18Pop of Red
Most preppy outfits you see tend to stick in a neutral color palette with a lot of tan, blue, and white. However, you can definitely rock a preppy outfit with a pop of color. Red is a stunning color choice because it always makes a powerful impact.
19Easy Casual Preppy Look
Instantly elevate even the simplest outfit with easy accessories. Tie a silk scarf around your neck and add a pop of color with a red shoe to add a preppy vibe to the casual outfit.
20Preppy Take on White Blouse
We weren’t kidding when we said white blouses are a preppy style classic! The large bow tie is a girly way to embrace the preppy aesthetic. Plus, the black and white in the blouse ties into the tweed skirt.
21Sweater Over Shoulders
Guys, if you really love the preppy style this outfit should be a go-to for you this spring and summer. Light colored pants and a white polo is completed when you tie a lightweight sweater around your neck.
22Simple Casual Outfit
The perfect outfit for running errands or going to lunch, using pieces you probably already have in your closet. Casual style doesn’t have to be complicated to look chic and embrace the style you love. We love the blue tones complimented with a pop of green with the handbag.
23Polo Shirt Style
You can’t have a list of preppy outfits without a polo shirt option – right? We didn’t think so. Try a long sleeve polo in bold stripes to add some brightness to your style.
24Easy Preppy Layers
Olive pants are a great alternative to the traditional khaki for menswear. The color feels fresh and modern, especially when paired with the right colors. Keep your layers simple with a gingham shirt under a lightweight sweater.
We love the unexpected layering in this outfit. Collared shirts and dresses are a sure fire way to embrace preppy style but you don’t want to get bored wearing them the same way all the time. Doing something as simple as adding a classic navy sweater over a collared dress makes it feel like a whole new dress.
26Elevated Sweater Look
Cable knit sweaters always look great during the cold weather months. Adding a plaid scarf and wool coat over the sweater adds a preppy flair that’s also functional. Guys, you can accessorize too!
27Suit Layering Done Right
If you’re looking for a way to play up your preppy style with a classic suit this is the look you need to try. Layering a thin sweater over a collared shirt, under a blazer adds depth and color to the look.
28Sweater Vest Prep
Sweater vests aren’t just for the Upper West Side, guys. We love how this sweater dress is styled for a business casual setting when styled with a collared shirt, tie and dress pants.
Turtlenecks are a big trend in 2019. While it can feel a bit constricting to wear a necklace with a turtleneck you can still accessorize it to give it a preppy touch. This oversized plaid scarf is the perfect addition to the casual outfit.
How cute is this outfit? Rainboots are a must for those rainy days, obviously. Even though it may be a rainy day it doesn’t mean your outfit can’t be cute! Recreate this outfit the next time you have a rain day.
31Classic Casual Vest
You likely have items similar to these hanging in your closet right now, but may not have thought to wear them together. Dress down a white collared shirt with jeans and a vest for a stylish casual outfit.
32Style a Windbreaker
Windbreakers have become a big trend recently, for men and women. We love this bold windbreaker styled with preppy classics for a stylish upgrade.
It’s all in the details for menswear. Seriously! When your clothes fit well, all you need is a few accessories to look great. Leather gloves, colorful scarf and boots give a simple outfit new life.
34Boat Ready Style
Nautical inspired much? White jeans should be in every woman’s wardrobe for their versatility. When worn with a striped shirt, boat shoes and colorful jacket you’re ready for the boat scene…or lunch.
35Zip Up Sweater Elevated
Tone down bright colors by layering a neutral color sweater with them. We love the preppy feel of this outfit, and the pop of color.