Break out your button-downs: From runways to retailers, preppy style is back in a big way. But while the trend itself is timeless, it’s certainly not static. Even if you’re not a fan of khakis and cardigans, the recent resurgence features plenty of less-than-classic ways to rock the classic look.
Wondering how preppy pieces first caught on? To prep (pun intended) your closet for warmer weather, we chatted with stylist and costume designer Ebony Brown about how the trend has evolved—and which style staples to stock up on.
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The history of preppy style
Starting around the late 1890s, preppy styles were a sign of privilege, associated with the Ivy League and the uniforms worn in upper-class boys’ preparatory schools (hence the name “preppy”). The trend slowly expanded beyond its menswear roots, evolving to include pieces like the plaid skirts and cardigan sweaters of the 1950s.
In the 1980s, brands like Ralph Lauren, Nautica, and Brooks Brothers brought the trend further into the mainstream, mixing in polo shirts and sportswear-adjacent styles, inspired by sailing and rugby team uniforms. By this point, preppiness had become partially about “taking the sports and bringing them to real life,” says Brown. Princess Diana simultaneously made her mark on the trend, sporting oversized blazers, crewnecks, and more. “If you wanted to think of preppy fashion, you thought of her,” says Brown.
These days, it’s safe to say some preppy styles are too cool for school—and in some cases, too risque. While prep-wear is “huge” again in 2022, as Brown says, the trend has gotten “a bit more edgy and a lot sexier.” For proof, look no further than the barely there Miu Miu miniskirt that took the fashion world by storm earlier this year. The tiny style generated a big buzz, becoming nearly as famous as the many celebrities who wore it, ranging from Nicole Kidman to Zendaya. “We’ve never seen preppy fashion like that,” Brown says of the viral style.
What’s more, the dark academia trend—featuring preppy styles in dark colors—has taken off on TikTok, giving the traditional trend a Gen Z-approved spin.
What does preppy mean now?
While the trend was once centered on all-American red, white, and blue hues, these days you can pick preppy styles in a range of shades. “Now, we're seeing the colors of spring infiltrate and infuse into it,” says Brown, as colors like lime green, orange, and neon—all of which are also very on-trend—can still give you that “preppy element.”
School doesn’t have to be in session to try academic-inspired outfits, either, as you can find several summer-appropriate, preppy style staples (albeit with a bit more coverage than the aforementioned micro miniskirt). Plus, with the trend going in bold new directions, you’ll find more prep fashions than ever that fit your personal style.
Serve up a stylish tennis skirt look
Think beyond country club courts with your tennis skirts this season. The sporty style, popular in the 1980s and 1990s, is back in a big way. Pair one with a crop top and blazer in the same color for a matching set moment. (Just call it a “game, set, match-ing set.”)
For a sporty yet stylish look, consider Alo Yoga’s Grand Slam Tennis Skirt, a pleated skirt featuring a fitted, hidden inner short with convenient side pockets. It’s available in four colors in women’s sizes XXS to L. If a flared A-line fit is more your style, try the Lululemon Court Rival High-Rise Skirt Long, which has a 4-inch liner and is available in nine colors in women’s sizes 0 to 20.
- Get the Grand Slam Tennis Skirt at Alo Yoga for $78
- Get the Court Rival High-Rise Skirt Long at Lululemon for $88
Layer on blazers or sweater vests
Another trend that’s popping up everywhere? Y2K nostalgia. To mix the two trends, top your tennis skirts or trousers with an oversized blazer. “We're in a really interesting year because we're having preppy fashion back, but we're also having 2000s fashion,” says Brown. “And with 2000s fashion, everything was extremely oversized. So now we're pairing that together.”
For a relaxed-fit style, try the Linen-Blend One Button Boyfriend Blazer from Express, which comes in black and pale pink in women’s sizes XS to XL. One reviewer calls the nylon and spandex blend “lightweight” and an “amazing blazer for summer.”
If you prefer a more classic, fitted look in men's sizes, however, you can’t get more preppy than a blazer from J.Crew. Consider the Ludlow suit jacket, which Prince Harry owns in several colors. It’s available in men’s sizes 34/S to 46/L in four neutral shades.
On cooler days or nights, add a cropped sweater vest for a dose of the dark academia aesthetic. Try the Jacquard-Knit Sweater Vest at H&M, which comes in four colors, including white and a summer-ready shade of yellow. It’s available in women’s sizes XXS to XL.
- Get the Ultra-Light Jacket at Uniqlo for $79
- Get the Ludlow Slim-fit Unstructured Suit Jacket in Irish Cotton-Linen at J.crew for $198
- Get the Jacquard-Knit Sweater Vest at H&M for $25
Shop breezy button-downs
What’s more classic than a crisp white button-down? For a lighter, summer-ready style, consider the J.Crew Classic Fit Soft Gauze Shirt. The brand claims the cotton fabric mimics the appearance of linen, while staying “super soft” and “more durable.” The versatile piece, which could go from the office to the beach, is available in five colors in women’s sizes 00 to 24.
For a similar look in men’s sizes, consider a Twillory button-down, like the Non-Iron White Twill Shirt. Our tester calls the brand’s customizable off-the-rack fit “phenomenal” and loves the “airy comfort” of the cotton. Try pairing it with a tie for an extra dose of preppiness, or layering with a light cotton sweater for cooler days.
If you’re inspired by the edgier preppy styles, consider the women’s cut SheIn Collared Crisscross Crop Top, which comes in four colors in women’s sizes XS to XL. “I love the string detail and it fits exactly how I wanted it to,” one reviewer writes. Or mix things up with a colorblocked button-down like the Puffed Cropped Poplin Shirt from And Now This, available in women’s sizes XS to XXL. Dress it up with trousers for returning to the office, or pair it with shorts for a breezy weekend outfit.
Another button-down in men’s sizes with a colorful twist? The Regent Regular-Fit Fun Sport Shirt from Brooks Brothers, a quintessential preppy label. The 100% cotton design, which features colorblocked stripes, comes in men’s sizes S to XXL.
- Get the And Now This Puffed Cropped Poplin Shirt at Macys for $50
- Get the SheIn Women's Collared Crisscross Crop Top at Amazon for $20
- Get the J.Crew Classic-Fit Soft Gauze Shirt at J.Crew for $90
- Get the the Non-Iron White Twill Shirt at Twillory for $99
- Get the Regent Regular-Fit Fun Sport Shirt at Brooks Brothers for $98
Invest in a good pair of trousers
To pair your button-down with pants, stock your closet with a new pair of trousers. The Way-High Drape Pant from Everlane, a high-waisted wardrobe staple, has a 4.5-star rating and 120 reviews. It’s available in women’s sizes 00 to 16 with either a 30-inch or 32-inch inseam. “They are unbelievably comfortable and roomy, the pockets are huge and the high waist is the best,” one reviewer says.
The J. Crew Straight Fit Flex Khaki Pant in men’s sizes is similarly top-rated, with reviewers calling them “nice summer slacks” made with “a very comfortable fabric.” It’s sold in 12 colors, including classic khaki, and comes in sizes 28/31 to 38/32.
- Get the Way-High Drape Pant at Everlane for $118
- Get the Straight-Fit Flex Khaki Pant at J.Crew for $70
Put your preppiest foot forward with some new kicks
Another runway-inspired trend? Mary Jane shoes. “Prada’s doing them a lot lately and so therefore a lot of other brands are knocking them off,” Brown says of the “back in style” shoes.
Try the Gwen Platform Mary Janes at Free People, which come in women’s shoe sizes 6 to 11 in three colors, including a summery white and tan combination. For a classic, non-platform Mary Jane, try the 8956 Smooth Leather Mary Jane Shoes from Doc Martens. They come in women’s sizes 5 to 11 in white and black. Mix the white pair with a cropped button-down and trousers for an edgier spin on summer style.
In men’s sizes, you can’t go wrong with the classic styles from Sperry, a brand that’s long been synonymous with nautical summer style. Try the Original Boat Shoe, which comes in men’s shoe sizes 4 to 16 in seven neutral shades.
- Get the Gwen Platform Mary Janes at Free People for $168
- Get the 8965 Smooth Leather Mary Jane Shoes at Doc Martens for $130
- Get the Sperry Men's Authentic Original Boat Shoe at Sperry for $95
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Prices were accurate at the time this article was published but may change over time.