How Black Creatives Are Pushing Preppy Style Forward

Polos and tennis skirts enter a new era.

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A collage of two model in preppy style outfits; white box pleated skirts and white tops while holdin...
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When Ralph Lauren launched its HBCU (historically Black colleges and universities) collaboration this March, the collection was met with mixed reviews. Some felt the iconic American brand, historically known for its association with Waspy collegiate and country club wear, suggested a certain nostalgia in the clothes for a time when people of color weren’t accepted in predominately white spaces. Critics weren’t comfortable revisiting an era, even aesthetically, of sit-in demonstrations and legal racial segregation. Still, while the line’s evocative imagery didn’t sit right with some, many others felt it was a necessary reframing to showcase Black models wearing a preppy style that African Americans may not always be associated with, but one that they have equal claim to — and have, in fact, participated in for over a century.

“I don’t think that deciding to wear or to want to create clothes that are speaking to a preppy history is so separate from Blackness as people might make it seem,” says Danielle Prescod, author of forthcoming memoir Token Black Girl and DEI consultant. “Because really it’s just like American clothes.”

Indeed, “American” style is reflective of the country’s identity: a big melting pot informed by the differing backgrounds of its artists, all coalesced into one rich, diverse culture. No one aesthetic can speak effectively to all our nation’s people, but in considering what fashion resonates as distinctly, quintessentially American, preppy clothing certainly stands out as one of the country’s defining modes of dressing. And Ralph Lauren is without a question one of prep’s pioneers, if not its most impactful force to date. The label is steeped in and inextricably bound to that pure Americana, from the red, white, and blue to the ever-present star spangled banner motif.

To Prescod, the iconic brand’s HBCU collaboration was simply a retelling of the history of prep in the U.S. that paid Black Americans their due.

“It seemed like a recognition that Black people had been erased from the narrative of Americana,” says Prescod. “When you look at the archival images of what the inspiration was, vintage pictures of Spelman students or Morehouse students, they are in direct conversation with anything else that was going on. There’s not really a difference between the Yale students in 1950 and the Spelman students in 1950, but because of the way that they were erased from the narrative, unless you are Black and you’ve grown up seeing those images or you have family members who participated in that culture, you might have been convinced that it’s a new thing or we weren’t there. The point is, we were always there.”

The aptly named “preppy” style gets its name from private college preparatory schools, where students have historically worn clean-cut pieces like crisp polos and knitted cardigans draped carefully over shoulders. It’s also strongly associated with country clubs, home of tennis skirts and smart golf dresses. Which is all to say: The look has close ties to affluence that are not exactly subtle. The venues for prep dressing, old money realms like social clubs and the Ivy League, are rooted in deliberate exclusivity and anti-Blackness. But as the style crests in mainstream popularity, with short pleated skirts, tennis dresses, and polos trending, it’s worth re-examining the role Black Americans have had in shaping the style and the creatives working to propel it forward today.

According to Kim Jenkins, fashion and culture educator as well as the founder of the Fashion and Race Database, one can’t discuss early Black prep without talking about pioneering American sociologist, historian, and author W.E.B. Du Bois. By the turn of the 20th century he was putting Black excellence on display, quite literally, during the Paris Exposition of 1900 with his Exhibit of American Negroes, sending a message to all onlookers about African American fluency in the language of sartorial codes.

“It showed people, ‘Look: we’re learned, we’re cultured, we’re literate, we’re living our best lives. Far behind us in the rearview mirror are the days of being enslaved,’” says Jenkins. “So you start seeing this with women who are going largely to Black colleges, HBCUs, as early as the 20th century. From the 1910s and 1920s, they were definitely embodying stylish dress, and this just becomes further refined in the decades to come, by the ‘40s and ‘50s, adopting the preppy dress that you would see at the Ivy League schools of their white counterparts.”

Jenkins also references tennis great Althea Gibson’s donning of classic tennis wear by the mid-century, noting how her mere presence in the arena, in her tennis whites, was taken as an affront.

“When we talk about the kinds of dress you’re supposed to wear in these very elite spaces, there is a qualification to have the ‘right body’ in them,” she says, noting that clothing meant for elite circles is often designed in such a way to present a boundary to the Black body. For example: pieces that are subtly (or not subtly) designed with no consideration for more shapely bodies or a larger backside. “Not to say that all Black women have the same kind of body, but when it comes to certain racialized bodies that are more curvy than not, that is a way that elitism can kind of remain intact, so that you can’t literally fit into those spaces,” explains Kenkins. “So Althea being in those spaces was a provocation in various ways. But then fast forward a few decades you’ve got Venus and Serena Williams creating their own lines.”

Althea Gibson’s tennis outfit, worn while winning the woman's singles title at Wimbeldon in 1957. Gibson was the first African-American to play in, and win, Wimbledon.Smithsonian National Museum of American History - Behring Center

In 2000, Venus Williams became the first Black woman to take the Grand Slam title at Wimbledon since Gibson’s back-to-back wins in 1957 and 1958. Williams’ clothing and lifestyle brand EleVen is an extension of her dominant on-court legacy. Her ascent to the status of American icon has a special significance considering the high volume of anti-Black commentary the Williams sisters have been subjected to for their entire careers in the world of elite sports. Whether it’s in athletics or the fashion industry, Williams is unfazed by the boundaries that have historically kept people like her out.

“I’m on a mission to continue breaking barriers,” says Williams. “I love tennis fashion because it is limitless and constantly evolving, just like EleVen — it’s so much more than just fashion.” She teases the launch of EleVen’s all-white Wimbledon collection later this month. There’s a strong symbolism associated with tennis whites; according to Jenkins, the style represents, like Venus says, something beyond simply clothing.

“Some interesting research on Althea Gibson and a commentary on class is when you get white clothing, one of the most important things is to keep it white and clean, which also could be commentary into Black culture with people wanting to keep their sneakers clean,” she says. “So this statuesque Black woman [Gibson] is moving into these kinds of precious spaces where the signature country dress are these tennis whites. The sartorial hurdle of wearing tennis whites, keeping them clean, Althea was able to do that and that was very important.”

The traditional pieces of country club prep attire like tennis whites remain staples of the aesthetic to this day, but brands like Recreational Habits aim to update the style by blending elements of modern Black fashion like streetwear-inspired couture with the classics. (Think a little less Carlton Banks, a bit more early aughts-era Kanye.) Partners Marlon and Jackie Skye Muller founded the label in part because the offerings on the market just didn’t appeal to them — it sometimes felt they were wearing a uniform that didn’t truly represent them just to feel appropriate in club sports venues. But their main motivation to launch the brand was a desire to populate the visual record with more images of racial minorities in the settings of elite spaces like club sports.

“Wherever we went, we were the ‘polka dots,’” says Marlon, describing how he and Jackie consistently found themselves to be the only people of color while skiing, golfing, or participating in any sport more associated with affluence. In hopes of normalizing the level of access they’d enjoyed to such activities, the couple wanted to first create a way for racial minorities to envision themselves in those historically exclusive arenas.

“One of the reasons we don’t connect with it is because we’ve never seen ourselves in those environments, right?” says Marlon. “A lot of the illustrations over the years have not been people of color; I learned the idea of fly fishing and camping through J.Crew ads and L.L.Bean ads over the years, and I wanted to do those things not because I saw myself, but because the images were so powerful. So the thought of being able to recreate those images based on showcasing people of color in these club sports and activities led us down the path of putting together product that would allow us to shoot those images and kind of recreate them.”

In making imagery with the goal of relating to people of color in particular, the pair hoped they might influence youth — including their own children — to imagine themselves in those affluent venues of prep dressing. “Our kids can see those pictures and say, ‘Oh hey I guess I can try polo, or tennis, or golf, and I don't have to feel that it’s this stuffy thing that only old people do,” says Jackie.

They recognize that the historic gatekeeping of these venues has led to a sort of generational gap: If one inherits a country club membership or has a love of polo instilled in them by a long line of players within their own family, the lack of diversity in settings like club sports doesn’t stand much of a chance at getting corrected. From its inception, the Recreational Habits brand has placed a strong emphasis on charitable efforts that align with its mission, so the Mullers have teamed up with youth groups like City Kids DC to create programming that addresses the barriers of finances and age in breaking into club sports. One such effort that they plan on expanding was a polo clinic, where adults were able to enter and learn the sport at a beginner’s level, and their patronage covered the cost of the youth clinics.

“We learned how to play polo and ride horses as adults, but it wasn’t an easy process,” says Jackie. “Everyone I can think of who plays or is around horses usually learned it from their parents or their grandparents; there’s no information online. We wanted to create an opportunity for adults to come and pay and play, so we were like ‘let’s go find them, maybe they want to learn!’ They actually came out and they loved it so those proceeds paid for the kids to participate for free. That’s the self-sustaining kind of charity model we would love to replicate within tennis and golf.”

Like Recreational Habits, many of the POC-owned brands in the prep attire arena are intentional about corporate responsibility efforts to support girls, underrepresented minorities, and those from lower income brackets. EleVen’s PrivilegeTax initiative prompts customers to donate to Girls Inc., a New York-based nonprofit advocacy group that stands as one of the longest running operations offering girls-only programming, at checkout. Ascot Manor, a Black-owned tennis apparel and activewear brand founded by Ahlilah Longmire, partners with schools and tennis organizations to identify youth in economic need and sponsor clinics, apparel, tournament registration fees, and other costs that come with playing competitively ranked tennis.

The Mullers add that another motivator in bringing young minorities into the fold of club sports is the ample opportunity for scholarships to respected institutions. Activities like lacrosse and crew are traditionally characterized by an extreme lack of diversity and many universities are invested in leveling their playing fields.

“In the inner city community we think that we have to excel at maybe three sports that we naturally have access to because they’re free: basketball, baseball, and track. It’s easy for you to see if you’re fast!” says Marlon. “But they don’t tell you in the community that being someone of color, if you fence through high school, you’re in the 90th percentile of getting a scholarship to any school and it’s the same with polo, crew, and lacrosse. If the amplification of that message was greater throughout America, you’d have more kids getting scholarships and getting that opportunity.”

For Recreational Habits, broadening the scope of an aesthetic tied to affluence to include more people of color is the mission; the clothing is simply a conduit.

“The most important thing in my opinion where you’re looking at what was typically exclusive, making it inclusive starts now with adults planting the seeds for the next generation,” says Marlon. “It’s one thing to make clothes, but it’s another to have a brand that stands for something greater than the product.”

Ahead, step your prep game up with the below edit of pieces from Black and POC-owned businesses.

We at TZR only include products that have been independently selected by our editors. We may receive a portion of sales if you purchase a product through a link in this article.

Best In Dress

“My look always reflects how I want to express myself,” says Williams. “When I want to feel powerful, I love wearing strong, colorful pieces, especially from my newest collection, Star Seeds, like the Moon Desert Dress in Fuchsia Snake.” Follow the champion’s lead and make a statement by choosing a bold color, or go the traditional route in a more muted neutral or classic white.

Top Marks

Dress your preppy fit down with a bra, tank, or crop top for more casual occasions, or consider the staples of the style — polos and sweater vests — if you have a particularly stringent club dress code to follow.

Bottoms Up

These summery shorts, skirts, and skorts are versatile activewear at its best: as at home on the golf course as they are running errands around town. Pair with a fitted tank or crop top for a sporty silhouette.

Zipping Around

Layers can still be necessary even in the summer months, and outerwear offers ample opportunity to dabble in some of the most emblematic elements of preppy style, like clean tailoring and sharp collars. Try a quarter zip for a more athletic feel, and to strike more of an Ivy League vibe, opt for a blazer or varsity style jacket with embroidered insignia to for an old school cool vibe.

Extra, Extra

These accessories will give you that country club chic effect no matter where you are — pair with any laidback ensemble for a style grand slam.

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