Sophistication, elegance, and classic charm—evergreen preppy style is a growing trend, and we’re here for it.
These looks are a breath of fresh air for your closet. They effortlessly balance comfort and class and are suitable for every season and occasion, from winter dinner parties to summer dates.
Read on to learn how to dress preppy and discover seven essential items for a chic, timeless wardrobe.
The preppy aesthetic originates from 1900s academic styles, like the chic college outfits Ivy League and boarding school students wore. The look carries sophisticated vibes and a heavy sports influence, like tennis and polo.
This style typically involves tailored silhouettes, muted colors, and long-lasting designs made of natural fabrics. It often has a nautical edge and equestrian inspiration (prep style loves riding blazers).
Preppy looks usually include core pieces like polo shirts, loafers, and chinos. Quintessential preppy brands like Ralph Lauren and Barbour are famous for this type of clothing, and many designers offer top-notch kidswear for your stylish little ones.
Find your unique style and build a versatile wardrobe with these seven preppy outfit ideas.
Blazers are foundational to the preppy look. Crisp and elegant, you can style them for nearly any occasion.
Try a navy blazer with a button-down shirt and a high-waisted pencil skirt for a subdued office look. Add nude heels and a designer handbag like a Fendi Peekaboo.
We also love a dark brown blazer over a tan sweater dress and ankle boots for a classy date night. Depending on your mood, you can dress it up with fine jewelry or tone it down with a wool scarf.
Discover gorgeous preloved blazers on ThredUp from top brands like J. Crew and Boden, starting at $5.99.
These lightweight bottoms are sleek, breathable, and perfect for either warm or brisk weather. Their straight-leg silhouette is similar to slacks, but they have a slim, tapered fit that’s suitable for less formal occasions.
For a relaxed weekend event, combine neutral-toned chinos with a cardigan and button-down shirt. To complete the laid-back aesthetic, add a pair of understated sunglasses and boat shoes.
Bring a little nautical flair to your next dinner party by pairing chinos and a polo shirt with a contrasting collar.
Thrift budget-friendly chinos on ThreadUp, starting at $5.99.
Polo shirts are a preppy wardrobe staple—flexible, sporty, and sleek. We love them for semi-formal events, casual meet-ups, and activities like tennis and horseback riding.
A stretch polo shirt paired with a white tennis skirt is the perfect preppy activewear. To find complete ensembles like this—or anything else—try our Style Chat. Describe your ideal outfits, preppy ideas, and experimental looks, and Style Chat brings them to life on an AI-generated person. Then, browse suggested items from our collection to make your idea a reality.
Shop thousands of polos in different colors and cuts on ThredUp, starting at $5.99.
The timeless aesthetic of button-downs offers a consistent solution to most outfit dilemmas—they look great with every piece of prep fashion, including cardigans, pleated skirts, and chinos.
Layer a plaid sweater vest over a white button-down to create an effortless holiday party outfit. Ankle boots and a trench coat look outstanding and add extra warmth as a bonus.
Preppy style typically loves perfectly tailored clothing, but we also adore an oversized button-down knotted over a shift dress. This is the perfect blend of casual and chic, especially with a pair of ballet flats.
ThredUp offers preloved button-downs from top preppy brands like L.L. Bean and Vineyard Vines, starting at $3.99.
Cardigans, turtlenecks, and cable-knit tops are vital to prep fashion. These pieces bring classic sophistication and academic aesthetics to every look you assemble.
Put together an eye-catching outfit with a cream turtleneck, dark blazer, and pleated skirt. We love this look for a lunch with friends or an afternoon shopping trip. Elevate it to pure elegance with knee-high boots and a sleek handbag.
Channel Ivy League vibes with a cable-knit sweater, chinos, and boat shoes for something more understated. Accessorize with a leather belt and a thin scarf (or a necktie, if you’re rocking a V-neck sweater).
ThreadUp has thousands of stunning sweaters for every personal style, starting at $6.99.
The right dress is a straightforward, effortless way to achieve a breezy, preppy look. Dresses are the perfect base layer and pair endlessly with other staples.
Our favorite combination is a solid shift dress with a blazer and boat shoes. Define the waist with a muted brown belt, and you’ll have an alluring date night outfit that only takes a few minutes to assemble.
Wear a polo dress for a sporty summer prep look. This is best as a simplistic outfit that speaks for itself, so we wouldn’t over-accessorize—but we still recommend a baseball cap or a headband.
Dive into ThredUp’s massive collection of preppy dresses, including polo dresses, A-line midis, and simple shifts, starting at $4.99.
Both these types of footwear convey a timeless prep aesthetic, but they’re slightly different—boat shoes have laces, and loafers don’t.
A button-down plaid shirt, chinos, and boat shoes make a relaxed ensemble perfect for exploring the town or lounging at home. It’s lightweight and comfortable yet chic and charming.
We recommend a similar look for your loafers. Just swap the chinos for a pleated skirt and add a blazer and thick, cable-knit socks. This style is more delicate and feminine—we’d wear it for a casual girls’ night or a romantic date.
Find your ideal pair of preppy shoes on ThredUp, with boat shoes starting at $6.99 and loafers starting at $6.99.
ThredUp is the ideal spot to elevate your preppy wardrobe. Discover your new favorite blazer or sweater vest in our vast inventory, where you can browse thousands of unique colors, sizes, and price ranges.
Use Style Chat to visualize your ideas before committing. You can generate an outfit and refine it until it’s perfect, using prompts like “Less color” and “More formal.” Once it’s perfect, browse relevant suggestions from our collection to bring your look to life.
Thrift preppy essentials—affordably and sustainably—on ThredUp.
Preppy fashion is easy to adopt because it uses so many versatile, core clothing items. Start by adding a few basics to your closet, like button-downs, polo shirts, and sweaters. Weave these essentials into your daily looks, and you’ll have the prep aesthetic down in no time.
Preppy-casual is a relaxed yet stylish aesthetic that blends classy pieces, like blazers and crisp collared shirts, with laidback items like sweaters and chinos. We love this style because it’s a chic solution for most occasions without compromising comfort.
While the standard preppy colors are neutral and earth tones, like beige, olive, and cream, it’s totally acceptable to add a splash of color. We recommend a pop of navy or coral for a vibrant palette that’s still elegant and refined.