Blame it on nostalgia’s omnipresent effects, but preppy style — fueled by peppy hues, precise silhouettes, stripes (so many stripes), and oft quirky layering — is undergoing a modern redux. But button-downs, khakis, and crewneck sweaters aren’t the only pieces soaring to the top of the must-have pile (though they most certainly have a place). For Spring/Summer 2021, it’s about creating a preppy capsule wardrobe of comfortably polished staples like rugby shirts, pullovers, novelty knits, and the warm-weather version of your beloved sweatpants — the sweatshort — for a collegiate-meets-cozy aesthetic.
“I think older millennials like me are feeling a deep sense of nostalgia for our youth and finding a newfound appreciation for how cool some of the cultural phenomena of our younger years really was,” Jack Carlson, founder and creative director of the witty and well-crafted classics label, Rowing Blazers tells TZR. Citing catalog-ordered rugby shirts, Brat Pack movies like The Breakfast Club, and old photos of Princess Diana rollerblading or attending a Polo match in her Ford Escort, he adds, “I think it’s this zeitgeist thing right now. We want to relive it all right now because we’re only now appreciating how good it all was.”
As the prep aesthetic continues to evolve and adapt within each era and season, Fred Segal’s vice president of merchandising, Ashley Petrie, says it’s always rooted in classic dressing principles. However, according to the VP, the current craving stems from the transformation of both streetwear and athleisure over the last 12 months. “With the world being on pause last year, prep offers a tailored and seasonless aesthetic. We’re beginning to return to classic ideas that we find comfort in,” she tells TZR. Adding, “It’s less about trend, and more about longevity and ease in your wardrobe right now.”
The idea of comfort undoubtedly drives the current flavor for pullovers, polos, and sweats, especially going into summer. The vibe is less layered popped collars for the show of it — back in the day, said styling cues amounted to a not-so-humble brag that you shopped certain brands and amassed a collection worthy of at-once wear. Now, showing your stripes (both literally and figuratively) is about subtlety and ease with a gym-class-chic vibe, to boot. Think: A crewneck sweatshirt layered under an oversize blazer (instead of an immaculate sweater) with a baseball cap. A crisp button-down French tucked into sweatshorts with loafers, not sandals. A half-zip worn with jeans or a fitted polo with trousers for a polished proportion play. A sweater vest topping your go-to tee with denim cut-offs, preferably a knee-grazing pair.
“The big thing is mixing high and low and mixing bright-as-hell colors with white and more subdued colors,” Carlson tells TZR. “Also, making sure that what you’re wearing has some kind of meaning; a visual ‘wink’ to those who are going to get it,” like a sun-soaked cap acquired on holiday, retro sport shorts (perhaps detailed with your school’s emblem), or a subtle logo from an under-the-radar label. Keep scrolling to discover and shop the 14 pieces you need to create the perfect modern preppy capsule wardrobe with additional insight from Carlson and Petrie.
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The Preppy Capsule Wardrobe Staple: A Novelty Sweater
A novelty sweater is a critical part of the preppy capsule equation, “but one that’s a little wry, a little highbrow, and well made,” Carlson tells TZR. “I’m biased, but I’m partial to the Warm & Wonderful sheep sweater or the Gyles & George ‘I’m A Luxury’ sweater, both favorites of Princess Diana’s. It shows you have a sense of style and a sense of humor.”
The Preppy Capsule Wardrobe Staple: A Rugby Shirt
When asked of the pieces to anchor a preppy capsule wardrobe, Carlson says, “A good rugby, of course,” which Petrie refers to as a “tried and true” striped staple.
“It’s for guys and girls, goes with everything, can be worn on almost any occasion, and nothing evokes that era better,” Carlson adds. For added femininity and flare, consider a puffy-sleeve style or waist-skimming crop.
The Preppy Capsule Wardrobe Staple: A Crewneck Sweatshirt
Much of the current preppy capsule game is mixing refined basics with athleisure essentials, like a crewneck sweatshirt — the fresh swap for timeless sweaters that otherwise feel automatic. “I prefer crewnecks to hoodies. They feel a little more timeless and lend themselves better to graphics,” Carlson says. “It’s a little more of a dad vibe, which I love.”
Petrie adds, “This is one of the best casual layering pieces you can add to your preppy look. It can also give a more modern feel when you add fun graphics or an unexpected color.”
The Preppy Capsule Wardrobe Staple: A Grosgrain Belt
You may recall grosgrain belts being one of those extras you could pepper into a school-approved outfit for added flair. Now, Carlson says they’re “a definite nod to the sensibility that we’re talking about,” making them a modern preppy staple. Other D-ring and fabric styles made with cotton and leather have a similar effect — for high style points, consider a luxury iteration, like Off-White and Celine’s new-season designs.
The Preppy Capsule Wardrobe Staple: Loafers
Petrie tells TZR that shoe selection is a crucial component of preppy style. “A uniquely colored leather loafer is always a good choice to add some personality to your classic aesthetic,” she says. “I’ve been living in cut-out penny loafers. They go with everything and add more polish to everything you pair with them.”
The Preppy Capsule Wardrobe Staple: A Knitted Polo
Polos in just about every hue from pastel shades to mega-brights were an Aughts staple. But ‘70s-inspired knitted polos have resurfaced for an even bigger throwback, with modern markers like overstated collars and bold color-blocking denoting novelty. “A knitted polo is one of my favorite items right now,” Petrie tells TZR. “I’m loving it in a modern cropped silhouette to tie back with high-waisted trousers.”
The Preppy Capsule Wardrobe Staple: Sweatshorts
With warm weather comes the need for abbreviated hems, and as sweats remain an integral part of most wardrobes, the sweatshort is the most current essential. For preppy appeal, it’s all about mixing in sharper staples, like a collared shirt, button-down, or pair of loafers.
While these easy shorts can be dressed up or serve as a casual work-from-home staple, Petrie has an important note about fit. “The more oversized, the better here,” she explains. “This is more of a day look and easier to pull off than most people think.”
The Preppy Capsule Wardrobe Staple: Trousers
When it comes to modern preppy style, Petrie tells TZR, “It’s all about a great-fitting pair of trousers that serves as the foundation for most of these looks. You can pair them with just about anything.” Among her current go-to outfit combinations: “A pull-on trouser for an easy everyday look with a fun crewneck sweatshirt for a more casual feel,” she shares.
The Preppy Capsule Wardrobe Staple: A Button-Down Shirt
A crisp button-down is an understated hero piece, with oversize versions as the fit du jour. “Shirting is the most universal out of all of the preppy items you can wear,” Petrie adds. “It goes [with] every single thing, whether it be layered underneath a sweater or sweatshirt or paired back with sweats for a more casual look.” Amp up the pep by opting for one in a sprightly shade or go the monogram route.
The Preppy Capsule Wardrobe Staple: A Cardigan
“A good cardigan is somewhere between a blazer and a sweater,” Carlson says of the iconic knit. “It also has grandparent vibes, which is a good thing.” Petrie agrees, referring to the cozy layer as “the best representation of prep.” When shopping for one this season, the Fred Segal VP suggests different textures and colors “to add something new to your wardrobe.” Whimsical details go a long way, too, like Alex Mill’s teensy front pocket or PH5’s romantically ruffled shoulders.
The Preppy Capsule Wardrobe Staple: A Sweater Vest
Sweater vests are synonymous with grandpas and sitcom characters like Chandler Bing on Friends, which is the exact vibe to strive for today: ‘90s-era normcore. “Color and texture are important when layering [a sweater vest] over a T-shirt or button-down,” Petrie says. Brimming with novelty, she adds, “[It] can add a lot of interest to an outfit by just layering it over simple pieces.” Try a classic white tee underneath, and finish with a vest in a fun print or bold color.
The Preppy Capsule Wardrobe Staple: A Half-Zip
Though many versions come sans hardware, this layering piece is a modern cozy must-have with a smart effect. Think country club attire, but refreshed. Try tying it around the neck for a preppy finish when you’re too warm to wear it outright.
The Preppy Capsule Wardrobe Staple: A Baseball Cap
Perhaps the buzziest accessory tied to the current preppy movement is the baseball cap, most notably, designs boasting a dad-esque vibe. Think styles you’d buy in a beach-town gift shop or one indicating an elite club membership. “A baseball cap is the best accessory to add some playfulness to your look,” Petrie tells TZR. “I really love a play on verbiage. It’s a fun way to add some dimension to the trend.”
The Preppy Capsule Wardrobe Staple: A Blazer
Like button-down shirts, blazers are heroic in the world of prep, and this season, boxy cropped fits are on the rise, though oversize shapes remain sartorial hits. “There is no article of clothing that can quite match the blazer both in pedigree and street cred,” Carlson says. “[It’s] both ineffably cool and deeply traditional, equally at ease on a boat or in the boardroom.” Adding, “Wear it with Oxford shoes, deck shoes, or no shoes.”
“The easiest way to clean up your look is throwing on a structured blazer to make it all come together in a much more polished way,” Petrie says. “I’ve been living in this yellow Simonett blazer; the color and the fabric give you a really fun spring moment.