Cover Story Serena Williams Is Embracing Her Evolution The Spring Issue
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the digital issue

Serena Williams Is Embracing Her Evolution

For the first time, the iconic athlete opens up about her new brand, WYN Beauty.

Evolution is a nonnegotiable part of the human experience. As we grow, so do our dreams and desires, transforming to reflect who we are in that moment and who we want to be in the future. At 9 years old, Serena Williams humbly told a CNN reporter she wanted to secure the number one spot on the junior tennis circuit one day. From her late teens until she retired from the sport, Williams set her sights on winning as many Grand Slam titles as possible (she won 23 singles titles—snagging her first at 17 and her most recent one at 35). Today, at 42 years old, the iconic athlete simply wants to be the best mother (she has two daughters—Olympia, 6, and Adira, 8 months) and businesswoman she can be. 

Though Williams is precisely where she wants to be and relishes being able to spend her days with her family in quiet Palm Beach Gardens, Florida, embracing a completely off-the-court life has undoubtedly been an adjustment. "It's definitely not easy," Williams says when asked about her decision to pivot away from professional tennis in September 2022. "I love sports and being active. Leaving something I was still good at to be a mom was such a difficult decision. But I wanted another kid, so I had to do that. Now it's about finding balance and doing other things I've always loved."

Serena Williams in a White Floral Skirt White Tank Top Yellow Baseball Hat

Kendall Bessent. Tank top: Ermanno Scervino, Skirt: For Love & Lemons, Knit Sweater: Bottega Veneta, Utility coat and hat: Nike.

Outside of tennis, Williams has always harbored a passion for beauty. Throughout her career, her uniform on the court featured ultracool hair and makeup touches that made her feel even more powerful. Early on, she and her equally stylish older sister and fellow tennis champion, Venus, famously wore beaded box braids while competing—a move that made every young Black girl feel seen then and now. Over time, Williams adopted an affinity for other beauty signatures like decked-out manicures, sharp eyeliner, and fluffy brows.

"Showing up [like that] was great for me," Williams says. "Tennis is different than other sports. Sprinters and gymnasts, for example, can wear a full face of makeup. With tennis, you can play for three hours and have sweat pouring down your face. So I had to find little ways to enhance my features. It started with the beads—that was a way to express myself. From there, I leaned into eyeliner and lipstick."

Williams' decades of experimentation with makeup paved the way for her newest venture, WYN Beauty. It's the makeup brand she dreamed of having each time she was tucked away in the locker room after a match, trying to quickly refresh her face before stepping in front of raving reporters. "Those moments are the foundation of the brand," Williams shares. "After playing on center court in front of millions of people, I'd have to do press. There was a point where I was talking to the press every single day. I had to figure out how I wanted to show up, but I only had a few minutes after a match to do my makeup."

Serena Williams Sitting in a White Floral Skirt White Tank Top Yellow Baseball Hat

Kendall Bessent. Tank top: Ermanno Scervino, Skirt: For Love & Lemons, Knit Sweater: Bottega Veneta, Utility coat, hat and sneakers: Nike, Watch: Audemars Piguet.

Her condensed routine often involved reapplying a layer of skin tint, a few dabs of concealer, and a quick swipe of eyeliner. Naturally, these items (and several others) are part of WYN Beauty's debut collection, available in over 680 Ulta Beauty stores and on Ulta.com beginning April 7. "It all started with the skin tint," she shares. "I would often mix my foundation and sun cream because I couldn't find a skin tint I loved. I realized that if I'm having this problem, other people are as well. I also remember talking to beauty publications, and they'd ask me about the products I couldn't live without. I'd list products like eyeliner and lipstick, which I often used on my lips and cheeks. From there, I started thinking about how I could create functional and really cool products."

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Williams has been working on making her thoughts a reality for five and a half years. Her first order of business was assembling a powerhouse leadership and product development team to bring her vision to life. She tapped Chidinma Asonye to serve as the chief brand officer and Christina Ximenez as head of product development. Asonye is a seasoned executive who oversees all of Williams' portfolio brands. Ximenez brings over 10 years of experience in cosmetic development, guiding strategy for companies like Morphe Cosmetics, Pixi Beauty, and Stila Cosmetics.

Together, they worked to carefully craft WYN Beauty's brand DNA and curate the 10-piece launch collection. The entire WYN Beauty range consists of Featuring You Hydrating Skin Enhancing Skin Tint SPF 30 ($29), Nothing to See Soft Creamy Concealer ($25), MVP Multifunction Lip & Cheek Color ($21), Word of Mouth Max Comfort Matte Lipstick ($20), Say Everything Max Intensity Featherweight Lipstick ($20), No Words Needed Lip Serum ($18), Big Vision Lengthening & Defining Tubing Mascara ($19), Glideline Waterproof Liquid Eyeliner ($21), Glideline Longwear Eye Pencil ($19), and Taking Shape Brow Shading Pencil ($19). 

Serena Williams Sitting in a White Floral Skirt White Tank Top Yellow Baseball Hat

Kendall Bessent. Tank top: Ermanno Scervino, Skirt: For Love & Lemons, Knit Sweater: Bottega Veneta, Utility coat, hat and sneakers: Nike.

Each item is housed in sleek chartreuse packaging, inspired by the countless yellow-green tennis balls Williams has served over the years. Every product is emblazoned with an encouraging shade name too. Case in point: The Featuring You Hydrating Skin Enhancing Skin Tint SPF 30 comes in 36 shades, ranging from Energy (the deepest) to Explore (the lightest).

WYN Beauty's offerings are vegan, cruelty-free, and dermatologically tested—something Williams was a stickler about. Hero products like the MVP Multifunction Lip & Cheek Color, for example, are powered by a trademarked blend called Truly Unstoppable HydraComplex—comprising moisture-retaining hyaluronic acid and glycerinplant-based squalane, and a coconut-derived texturizing agent. "I wanted to create [a collection] people could use every day to enhance their natural beauty," Williams says. "I wanted to focus on long-wearing, 'clean' formulas because that's how I live my life. I have a farm and try to eat 'clean,' so I also apply that approach to what I put on my face."

The brand also embraces an "active beauty" ethos; every formula is smudge-, sweat-, and feather-resistant. Crafting products that can keep up with beauty consumers' busy lives was of paramount importance to Williams. "I am not working out as much, but I am so active in my day-to-day life," she says. "For me, it's about creating a collection that speaks to me, whether I'm on the tennis court or picking my daughter up from school. A little goes a long way with what we've created with WYN Beauty. If I wake up late, I can quickly put on our skin tint, concealer, and lip and cheek tint and look fully made up all day. WYN Beauty wants you to understand you can be glamorous and active—and own it."

Serena Williams Pink Dress Black Gloves Chickens Farm

Kendall Bessent. Full look: Joy Cioci, Boots: Burberry, Gloves: Stylist's own, Earrings: Saint Laurent, Watch: Audemars Piguet.

Williams has had an intentional hand in every aspect of the process—from conception to production—and was steadfast about perfecting each product. "The [liquid] eyeliner was challenging because developing a 'clean,' waterproof formula is almost impossible, but we did it," she says. "Creating the mascara was also hard because I wasn't going to let the quality slide. I wanted to make a mascara that coats and covers each eyelash to give you that lengthened look. I'm really happy with how those two products turned out."

Now that WYN Beauty is here, Williams joins the fast-growing legion of Black women beauty founders. Considering the cosmetic industry's problematic track record, a continued uptick in diverse beauty entrepreneurs is needed. Despite Black consumers spending billions on beauty each year, we were greatly underrepresented on the shelves for decades. It wasn't until the late 2010s that there were more than a handful of makeup brands delivering products for melanin-rich skin and inclusive advertisements.

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"Back then, brands [made us feel like] we had to fit their standard of beauty," she says. "When I was traveling 20 years ago, brands didn't offer 40 shades. Many products weren't made for Black skin. We had brands like Iman Cosmetics and Black Opal, but they weren't always available where I was. I had to learn to do my makeup so I could present myself in the best way."

Taking up space in a market that hasn't always included—let alone celebrated—women of color means the world to Williams. Her presence in the industry is even more moving, considering how her beauty and body were focalized on the court. In the Western world, Black women inherently don't fit into the Eurocentric standard of beauty, and society reminds us of it at every chance. These reminders are further omnipresent for Black women in tennis, as the sport has historically been predominantly white. As of 2023, people of color comprised just 38% of the United States' tennis-playing population, according to the Physical Activity Council Study on Sports and Physical Activity. 

Being a muscular, curvy Black woman in the sport, Williams was subjected to vehemently racist and sexist rhetoric from spectators and commentators. But one thing about Williams is that she has always embraced who she is and what she looks like unapologetically. "I never wanted to fit into a box," she says. "I don't look like anyone else and never will. I was one of the first athletes [in tennis] that had a differently shaped body. I felt I've pioneered in so many different ways, so I wanted to include beauty in that."

Serena Williams in a Pink Dress with Black Gloves on a Farm

Kendall Bessent. Full look: Joy Cioci, Boots: Burberry, Gloves: Stylist's own, Earrings: Saint Laurent.

Williams is aware that she's entering the market at a time when the number of celebrity-led beauty brands has reached an all-time high. While some may be fatigued by the influx, there's no denying that the growth and demand are there, especially for brands that offer innovative, inclusive products. NielsenIQ reported that the sales growth of celebrity beauty brands surpassed the growth of the total beauty category in 2023, up 57.8%. Its research also found that the segment of consumers purchasing celebrity beauty brands grew 21.9% compared to 2022.

Williams is adamant WYN Beauty has more to offer beauty buyers than just her name. "It's not about [the celebrity title] for me," she says. "This brand is for everyone—it doesn't matter who you are. We've drawn from my experiences and everyday life to reach everyone and fit their needs." 

Serena Williams Pink Dress Black Gloves Chickens Farm

Kendall Bessent. Full look: Joy Cioci, Boots: Burberry, Gloves: Stylist's own, Watch: Audemars Piguet.

While WYN Beauty provides tangible tools to build a true-to-you beauty routine, Williams wants the brand to impact people in intangible ways as well. Through the brand's empowering philosophy and imagery, she hopes WYN Beauty can make people feel just as good on the inside. "It's about more than just products," she says. "I hope [we] make it easy for our community to feel and look their best—however they may define that."

The way our beauty routines can influence our mood, shape our core memories, and encourage us to cultivate a deeper relationship with ourselves are all ideas that resonate with Williams. She still vividly remembers her first encounters with makeup. "My earliest beauty memory has to do with my mom," she recalls. "She wore red lipstick back then and still does now. I remember playing in her makeup as a kid."

Now that she is a mother, those moments have come full circle with her daughters. Getting to share her makeup rituals with Olympia (and, one day, Adira) has made her reflect deeply on her relationship with inner and outer beauty. "The way I talk to myself about beauty has certainly changed throughout my life, and it will continue to evolve," she shares. "Motherhood has allowed me to look at beauty through the eyes of my daughter, Olympia. We're always experimenting with makeup together, and I think about how these moments will be part of both of our beauty journeys."

Serena Williams White Fluffy sweater blonde curly hair lying down on the grass

Kendall Bessent. Kendall Bessent. Oversized knit: Stella McCartney, Earrings: Saint Laurent, Flower Handbag: Margiela, Boots: Nike, Socks: Stylist's own.

Williams' motherhood journey has also shaped the philanthropic initiatives she wants to launch through WYN Beauty. She wants the brand to be a fervent advocate for maternal health, largely due to her near-death birthing experience with her first daughter. Williams had to undergo an emergency C-section, which later led to a pulmonary embolism and hematoma in her abdomen. Her emotional and physically taxing labor story was vividly documented in her 2018 HBO series, Being Serena, which shone a light on the realities of the maternal health crisis in America and abroad.

"Maternal health is a cause that's very personal to me after the life-threatening experience during the birth of Olympia," Williams expresses. "It's important to me that WYN Beauty plays a role in supporting mothers from all backgrounds in different stages of motherhood. We will platform causes and initiatives that support maternal health and will champion members of our community who are doing the same." 

Williams has always possessed a benevolent spirit. When she's riled up about a cause, she'll do anything she can to make a difference. And as her affluence has grown, she's repeatedly leveraged her far-reaching platform and financial resources to enact change. Leveling the playing field for women and people of color in business is another way she's committed herself to moving the needle.

Serena Williams laying down on grass in a white fluffy sweater with curly blonde hair

Kendall Bessent. Oversized knit: Stella McCartney, Earrings: Saint Laurent, Flower Handbag: Margiela.

She launched her venture capital fund, Serena Ventures, in 2014 after learning that female-founded businesses received about 2% of the total capital invested in venture-backed startups in the United States. "My VC fund, Serena Ventures, aims to empower everyone to have a seat at the table, regardless of who they are," she says. "We have had the privilege to invest in so many diverse founders—particularly women and people of color, who receive a disproportionately small amount of total venture capital funding—to change the world with their ideas and products. Serena Ventures has invested in a wide range of companies across industries."

According to Serena Ventures' website, the organization has invested in 77 companies so far. When it comes to beauty and personal care, Williams has thrown her support behind disruptive brands like Parfait, Billie, Mayvenn, Olly, and Lola. Some businesses are backed by an inaugural fund—Williams raised $111 million for her VC firm in 2022—while others are funded by her angel investment. In a candid TikTok posted in March, Williams shared that 14 of the companies she has invested in have reached unicorn status, meaning they're valued at over one billion dollars.

For so long, Williams herself was considered the brand. When she turned pro in the '90s, her incredible tennis prowess made her a globally recognizable star, and she seized lucrative, front-facing endorsement deals. When you first enter the limelight, your name and talent can open some doors, but from there, it's up to you to continue breaking the rest down and solidifying your personal brand. Williams' career has been a master class in doing that (and then some). Over the last three decades, her business savvy has allowed her to parlay her grand on-the-court career into something even more monumental. Now, she's the one building brands behind the scenes and showing others what's possible when you fully lean into your purpose.

Serena Williams White Fluffy sweater blonde curly hair

Kendall Bessent. Kendall Bessent. Oversized knit: Stella McCartney, Earrings: Saint Laurent, Flower Handbag: Margiela, Boots: Nike, Socks: Stylist's own.

WYN Beauty is the latest addition to Williams' vast business repertoire—and it's certainly the mogul's most personal endeavor yet. "Beauty has been part of every era of my life, from the court to the red carpet," she says. "WYN Beauty is an extremely personal undertaking. It's a brand that's evolved from my lifelong passion for makeup, and the entire collection is authentic to who I am—from the 'clean' formulas to the inspiring shade names to the chartreuse packaging that pays homage to my career in tennis. My personal best has changed over the years, and WYN Beauty is the next evolution of my beauty journey."

When your life has been marked by over 30 years of groundbreaking accomplishments—to the point where you're regarded as the "greatest of all time" in tennis—summarizing what you want your legacy to be is an impossible task. So Williams simply opts not to think about it. Instead, she chooses to be grateful for all she was able to do as a professional athlete and looks toward her limitless future as a mother, wife, and entrepreneur.

However, when asked what has brought her the most joy in her 42 years of life, Williams will reply without hesitation. "My kids," she says. "I can't say that a Wimbledon trophy holds a candle to volunteering at my kid's school."

Serena Williams posing in a pink dress with yellow boots in front of white stables

Kendall Bessent. Full look: Joy Cioci, Boots: Burberry, Gloves: Stylist's own.

Every day, she strives to look like a hero in Olympia and Adira's young eyes. By allowing her little ones to get a front-row seat to her life as a beauty founder, tennis trailblazer, and philanthropist, Williams hopes to inspire them to pursue whatever sets their hearts on fire. "I want my daughters to look at my career and learn that being authentic to themselves is really the most important thing," she shares. "You don't have to be the best as long as you do your best. I also hope my daughters see how many different passions I have—from tennis to beauty—and learn that they can lead dynamic careers and lives across their many interests." 

On any given day, Williams might travel from her daughter's school to the grocery store and then to a meeting for WYN Beauty. This type of hustle and bustle looks much different than the years she spent jet-setting across the globe for tennis matches like Wimbledon or the Australia Open. But Williams wouldn't trade her new reality for the world. The life she's created in her sunny South Florida suburb brings her infinite happiness, peace, and comfort. And she deserves every bit of it. For Serena Williams, this is exactly what evolution looks like. 

Talent: Serena Williams

Photographer: Kendall Bessent

Beauty Direction: Hallie Gould

Creative Direction: Jenna Brillhart

Hairstylist: Angela Meadows

Makeup Artist: Natasha Gross

Manicurist: Tawnee David

Stylist: Kimberly Sussman

Styling Assistant: DaRius Kenon

DP: Agape Lataillade

Assistant Camera: Ron Gesualdo

Photo Director: Kelly Chiello

Production Assistant: Amanda Lauro

Booking: Talent Connect Group

Article Sources
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  1. Meeting the needs of Black beauty consumers in 2023. (n.d.). NIQ. Retrieved March 28, 2024, from https://nielseniq.com/global/en/insights/analysis/2023/meeting-the-needs-of-black-beauty-consumers-in-2023/

  2. Growths in ethnic diversity behind latest surge in tennis participation, study finds. (n.d.). Retrieved March 28, 2024, from https://www.usta.com/en/home/stay-current/national/growths-in-ethnic-diversity-behind-latest-surge-in-tennis-partic.html

  3. Celebrity beauty brands: Key success drivers in 2023. (n.d.). NIQ. Retrieved March 28, 2024, from https://nielseniq.com/global/en/insights/commentary/2023/celebrity-beauty-brands-key-success-drivers-in-2023/

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