All-American: Venus & Serena

Episode 7: Style Points

TV Journalist: So I'm going to go a little bit away from tennis. Okay. And I have to talk about your outfit. 


Serena Williams: Ok. 


TV Journalist: Now, when I. First saw. It, I said, this is the best thing I've ever seen. And you had some outfits. 


Serena Williams: Yeah. 


Cecil Harris: Serena Williams. Look at the 2021 Australian Open was a bold, asymmetrical bodysuit with big blocks of pink, red and black. The ensemble was inspired by Florence Griffith-Joyner, better known as Flo-Jo, the fastest and most stylish sprinter in women's track and field in the eighties. 


Serena Williams: I think this is one of the best ones, though. I mean, it's been so high. You know, I always like to say, like, okay, how do I out do it? But I think we all did it this time. 


Cecil Harris: Serena is used to making waves with her on court, looks at nearly every tournament she plays. She and her team at Nike create something special for her to wear. Serena has been sponsored by Nike since she was 22 years old when she first signed a $40 million contract with them. 


TV Journalist: And the colors. Who came up with the color scheme? 


Serena Williams: They came up with the color scheme. So they they did everything with this design. I keep texting them after every day. I'm like, Oh my God, this is one of my favorite. There's definitely top three. Definitely top three. 


Cecil Harris: Another reporter asked her which outfits were in her top three. 


Serena Williams: It's still debating. I definitely think the jeans skirt has to go in there with the boots. I really was thinking that I need to put lay all out and decided it's tough because I am obsessed with tutus, so that has to be in there somewhere. 


Cecil Harris: Serena Williams is one of the only players in all of professional tennis who gets to choose what she wears. Even some of the most exceptional tennis players will have big sponsorships with companies like Nike, New Balance or Adidas. Those players just have to wear what they're given. But if you're a Williams sister, you get a say. And for Serena Williams, this tradition of choosing her own outfits started long before her partnership with Nike. So today, we'll tell you about how the sisters first got a say in what they wore on court, how that reshaped tennis fashion, and how this change was all part of Richard Williams plan to have his daughter succeed beyond their sport. Hi, I'm Cecil Harris, and this is all-American. Venus and Serena. Episode seven Style Points. Before Venus and Serena, getting a big brand sponsorship as a black woman in tennis was tough. Take the example of Zina Garrison. Zina was a top player on the Women's Pro Tour in the eighties and early nineties. She also won two Olympic medals in 1988. But for most of her career, she was unsigned, which meant she didn't have a clothing sponsor. Agents told her she didn't have, quote, the look seemingly because she is black. After all, white players ranked lower than Xena did have clothing contracts. Zina played professionally for almost a decade without a clothing sponsor. But things finally changed in 1990 when Zina made it all the way to the Wimbledon final. 


TV Journalist: 6-4, 6-1 for Zina Garrison. A dream trip to England. And hardly a nightmare for her. Her best ever Grand Slam appearance. 


Cecil Harris: Zina did not win the Wimbledon final, but she was the first black woman to make it that far since Althea Gibson in 1958. Still, for most of the tournament, Xena competed in borrowed clothes without a sponsor. And it wasn't until she made the final that Reebok took notice and offered Xena a contract. In other words, in order for Xena to be offered something, a lot of white players with lower rankings already had. She had to make history. 


TV Journalist: Will you be back on this court vying for a title? 


Zina Garrison: Definitely. I love that trophy. I'm going to get it one way or another. 


TV Journalist: Congratulations, Xena and magnificent tournament. Xena gets a look at her. She was in the final. Wonderful. Thank you. Xena Garrison. 


Cecil Harris: In the years after Xena Garrison signed her contract with Reebok. Venus Williams was a phenom on the rise. And in 1995, shortly after she turned pro, 14 year old Venus signed a $12 million deal with Reebok. A deal that big was unheard of for a player with Venus's limited experience. Marketing experts believed that Venus would be a big draw for an audience. The brand was trying to attract young black women. Venus deal with Reebok was unprecedented in another way, too. The company wanted to design for Venus. Reebok designers said they worked closely with Venus to design outfits she would be comfortable wearing, like denim shorts, shirts and overalls. Meanwhile, 14 year old Serena didn't really have a distinct look because she didn't have an endorsement deal yet. Her profile wasn't as big as her sisters. After Serena turned pro in October of 1994, she just wore whatever complementary clothing Nike would give her. An important thing to note about tennis attire is that it's historically been very conservative. The tradition of wearing tennis whites still lives on today. 


Amy Denet Deal: When you think of that time in tennis design, it was still a lot of polo shirts and pleated skirts and things that are so antiquated. For somebody that has that strength and moves at the speed of light. Right. 


Cecil Harris: Amy Denet Deal was working as creative lead designer at Puma in the mid-nineties. Amy said she used to watch the Williams sisters play tennis, and she was just completely mesmerized by them. 


Amy Denet Deal: They were so assured of their movement and their power in the sport that it was like to me, yes, I love watching tennis, but more than anything, I love movement. I love the way humans move and especially how they move in athletic clothing. It was this power and grace that they both possess within that sport. And then, of course, crushing competition. But they were just stunning and beautiful to watch. 


Cecil Harris: In 1997, Amy got some exciting news. 


Amy Denet Deal: It was kind of hush hush, so we all kind of found out about it. Same time, I think I went into my office, closed the door and just like squealed. I was like, Oh my God, I cannot believe this was the coolest thing ever. 


Cecil Harris: 16 year old Serena signed a deal with Puma worth about $12 million, which meant Amy would be designing for Serena Williams. 


Amy Denet Deal: We had not seen women of color rise in the sport. So to to identify with that, to get to design for one of them, it was like, pinch me, pinch me, because I could not believe that I was at that place in my career. 


Cecil Harris: In early 1998, Amy flew from Pullman's headquarters in Germany to California to meet Serena in person for the first time and present her with some ideas. Amy was struck by how prepared teenage Serena was. 


Amy Denet Deal: She had so many ideas to talk about. We showed some initial sketches. She gave great input. And that's really where we take her ideas, which were like kind of hand-drawn. So I think the key was that even at that young age, she had such a vision of her own self, you know, because I think most kids, if you think most 16 year olds, you show up with something and they're just like, Yeah, whatever, what's going to make me look good? Or they'd be kind of shy, but like, she totally knew who she was and what she wanted to be wearing. 


Cecil Harris: Serena wanted something bold. 


Amy Denet Deal: You know, the first thing we talked about was color. Like, what can we do? Everything except white, you know? So that was, like, such a different perspective from a teenager that had these ideas. So she was looking more towards things that we probably would have been designing for more of a body wear collection or a swimwear collection, because that worked for her. She didn't want to have a lot of things of extra fabric. She wanted everything bodycon. So that was wonderful because the fabrics that were available at that time were far enough ahead to be performance items for her as that woman in sports. 


Cecil Harris: After the meeting, Amy went back to Germany and got to work. Serena debuted her first Puma outfit at the 1999 U.S. Open, as you'll remember from episode three of this series. This is where Serena won her first major tournament after defeating the Swiss Ms.. Martina Hingis. 


Serena Williams: I would like to also thank my dad and my mom because they have been great parents with all my sisters in the sport and former first lady with whom I clothing. They're great. You should get out some get some, too. 


Cecil Harris: And when we spoke with Amy in early 20, 22, it had been a while since she had seen Serena's debut look. So my producer Albert had a photo already. 


Amy Denet Deal: Oh, my gosh. Oh, my gosh. And that was at a time where she matched to beads to her outfit all the time, which was amazing. 


Cecil Harris: Can you just describe this outfit? 


Amy Denet Deal: Just look how beautiful she looks. Oh, my gosh. So that outfit was actually based on more of a cross-training look. And then that time in the athletic industry, it was like more sport bras and tank tops that were done for yoga or body wear items. So to be doing this in tennis was really a new thing. 


Albert: What about the color? 


Amy Denet Deal: Yellow was really to show her radiance the glow. I always think of that inner glow and that inner vibrancy she had. So that was really one of the first colors that we had. Was this just Sunbeam Yellow? Because she was I mean, like, look at her smile. Look at her face. I mean, that was really that young girl that had that exuberance and just so excited about her career in the sport. 


Cecil Harris: Serena's outfit was a big hit. Puma sales shot up, and overnight the brand became a hip tennis brand. 


Amy Denet Deal: That was just such a huge day for Puma. You know, that was a huge day for her family. It just was so beautiful to watch someone so deserving of that moment and to be involved in it in some tiny little way. And, you know, that was the beginning. That was the beginning when they started just changing how the industry would, you know, accept and treat women of color. There were so many changes that were you know, they were the ones that were breaking all that ground and making that shift in an industry that was so stuck. 


Cecil Harris: A year after Serena's 1999 U.S. Open win, Venus won it, too. And just before that, she won Wimbledon in 2000 and a few months later. Venus signed a new contract with Reebok, this time worth $40 million over five years. It was the biggest guaranteed endorsement deal ever for a female athlete at the time. Reebok was betting big on this new deal with Venus because the company had some catching up to do. Their sales had fallen behind Nike and Adidas, so they were hoping Venus could help them turn things around. 


TV Commercial: When you see my Venus, you want. Time. When you see that Venus, she's mine. 


Cecil Harris: Reebok first aired this ad with Venus on the first episode of Survivor two in 2001. The ad was for a collection they designed around Venus called Defy Convention. In this commercial, Venus looks glamorous and sporty. She kicks a ball into the air while wearing a fancy gown. She kisses a Reebok sneaker. The Wall Street Journal wrote at the time that, quote, By casting an athlete in a non athletic role, Reebok hopes to build the perception that folks who wear its goods are iconoclasts. Now, every time either sister stepped onto the court, there was an opportunity for the sisters and the brands they were wearing to make a fashion statement. And one of the biggest fashion statements in tennis history came from Serena at the 2002 U.S. Open. Here she is debriefing with an on court reporter about her first round match, what he had to ask about her outfit. 


TV Journalist: Before I let you go. Tell us a little bit about your outfit tonight. Did you design this? 


Serena Williams: Yes, I knew who. Design is like a little catsuit, you know? It makes me run faster and jump higher. It's a really successful design. It's really sexy. So I like it. 


TV Journalist: I agree with that wholeheartedly. Congratulations, Serena Williams. 


Cecil Harris: As cringeworthy as this reporter's comment was, Serena's outfit truly was unlike anything tennis had ever seen. The catsuit was shiny, black and form fitting. She paired it with blond braids, a pink headband, and a $29,000 Harry Winston bracelet. The catsuit was made out of Lycra, a spandex brand that looks like leather. It was inspired by the Halle Berry movie Catwoman and was designed by one of Aimee's colleagues at Puma. 


Amy Denet Deal: It's something that had not really been worn on a tennis court. She's not in a dress. She's not in a skirt. She's in a body conscious piece that's built for performing and for power and support. But it's not anything about this antiquated version of what women are supposed to wear when they play a sport. Right. So that's really the breakthrough moment for me, is that it just doesn't buy into any of that previous notion of what women are supposed to wear in order to play tennis. 


Oprah Show: Oh, you know. 


Cecil Harris: The Oprah Winfrey Show was the biggest talk show on TV in the early 2000s. Being a guest on Oprah meant that you had reached a certain level of fame. You were a household name. And in late 2002, at 22 and 21 years old, Venus and Serena had reached that level. 


Oprah: How did you feel when you're tattooed made headlines around the world? 


Cecil Harris: Oprah smiled as Serena took a moment to think about the question. 


Serena Williams: I love design, I love fashion. I love being involved with that. And I didn't really expect it to make. It was different. It was definitely different. But I expected to make such a big hit as it did. 


Cecil Harris: The reaction to the catsuit wasn't all positive. CNN anchor Anderson Cooper opened his program with, quote, the controversy over the catsuit. A Washington Post fashion critic said it looked trashy, but the Williams sisters held a key belief when it came to fashion and tennis. 


Venus Williams: If you aren't wear anything that you're confident in, you aren't going to play well, we don't. If I'm not wearing something, I never wear anything. I don't like it. Don't look. I'm pretty good. 


Cecil Harris: Serena agreed. It was simple. 


If you don't look Good, you don't play well. 


Cecil Harris: The sisters were ranked number one and number two in the world, looking good and playing well was working for them. But remember, Richard's plan for his daughters was always to go beyond tennis, and by the early 2000, they were headed in that direction. 


TV Commercial: And now the world premiere of Venus and Serena. For real. 


Venus Williams: People often ask us what we think about doing a match, which think about winning, but we also worry about losing. 


Cecil Harris: Venus and Serena for Real debuted in 2005 on ABC Family. The sisters used the reality show to change how people thought of them. 


Venus Williams: Think about music and fashion and design and the future. Yeah, we tennis players, but we're a whole lot more. A lot more wrapped up. 


Both Venus and Serena went to fashion school in the early 2000s, which eventually led them to launch their own brands. Venus has an interior design company called VS Star Interiors, and in 2007, she launched her own tennis clothing line called 11. Serena, meanwhile, started a fashion line in the mid 2000s called an heiress, which is Serena spelled backwards. She sold a mattress designs on the home shopping network. Serena has since gone on to start other businesses, including a size, inclusive clothing line called Esse by Serena. As Serena's fame has grown. She's also been thoughtful about elevating her personal look. We tracked down her stylist, Kesha McLeod. 


Kesha McLeod: I am formerly titled a Wardrobe Stylist, but I like to consider myself more of the creative director or visual architect realm because I'm kind of more branched Out than that Than just putting looks together. 


Cecil Harris: Kesha has been styling Serena for more than a decade. She picks and designs Serena's dresses and outfits that you don't see on the tennis court. Keesha also styles other pro athletes, including NBA players PJ Tucker and James Harden. We showed Keisha a picture of Serena's iconic 2002 Puma catsuit, the one she paired with a pink headband and blond braids. And Keesha was struck by how much Serena's hair in this era reminded her of her own at that time. 


Kesha McLeod: I Was blond all through high school. I did blond braids and I did blond hair. So it's kind of like a crazy, like, eerie thing that, you know, you're showing me this and like hey, where were you at this time? And I'm like, in high school with blond hair watching her on 106. And part of her and I were destined for each other, which are really ironix. So it's kind of like an inside joke to me right now. I can't wait to share this with her. 


Cecil Harris: Kesha says she definitely used to emulate the look of the Williams sisters when she was in high school. She even wore beads in her hair. She originally met Serena in 2010 through another pro athlete client of hers, Vernon Davis. A tight end for the 40 Niners. When Keisha booked her first gig with Serena. She was a bit starstruck. But it went well. 


Kesha McLeod: It was outfitting her for events for the Dallas Super Bowl, and we kind of hit it off, and the rest is history from there. 


Cecil Harris: As Serena star rose, the events keesha outfitted for her got bigger and bigger. From super bowl parties to oscar parties and behind every red carpet appearance. There's usually a bit of a story. For example, in 2014, Serena was headed to the Vanity Fair Oscar party, but the dress designed for Serena was a near disaster. Serena's dress was made of white floral lace with a tinge of pink, and it was held together with some sheer fabric which was supposed to be nude. But the designer made it for a light skinned nude. 


Kesha McLeod: And not black woman nude. And so on the way to the Vanity Fair party, I had to literally with a beautyblender dab in. 


Cecil Harris: If you Google a picture of Serena from that 2014 Vanity Fair Oscar party, you can see Kesha's handiwork. 


Kesha McLeod: That's all foundation. That's all her foundation in the brown parts. 


Cecil Harris: The nude parts of the dress blend perfectly with Serena's skin. The dress was a hit. In fact, Kesha says that Serena loved the look so much, she used a photo of it as her phone's screensaver for quite a while. Keesha and Serena have worked together on a lot of looks. But around this time, as Serena settled into her thirties, her fashion sensibilities were starting to evolve. 


Kesha McLeod: It goes from something of looking at that Victoria Beckham dress and not letting it be chic office, but embracing adding sexiness to it. 


Cecil Harris: Kesha is referring to one of Serena's looks from 2012 when she guested on David Letterman. Serena wore a Victoria Beckham red belted dress with $4,000 Christian Louboutins. It almost looked like she was headed to a business meeting. In 2014, Serena was invited on Letterman again. He announced earlier that year he was retiring. So Serena knew it would be her last time guesting on the show. 


Kesha McLeod: She would always hit David Letterman for years. And because that was his last year, she kind of wanted to go out with a full band. I remember her texting me. She wants to go in a different direction. 


Cecil Harris: Her final look. Black ankle hugging, high heels, a matching crop top and a stretchy white pencil skirt. Serena looked chic and sporty. In fact, the outfit was versatile enough that it allowed Serena to play a little tennis as part of her appearance on the show. Serena and Letterman hit tennis balls back and forth in front of a crowd on a blocked off New York City street. 


Dave Letterman: I think I can beat her. 


Cecil Harris: Then they took turns hitting the ball as hard as they could against a window. 


Serena Williams: You think you can break it? You try to break this swing. I'll try it. Let me try it. 


Cecil Harris: Dave could not break it. So he passed the task to Serena. 


Dave Letterman: On the big. Friday's big one. Let's see what happened. Hey, Rupert. 


Cecil Harris: Serena broke the window. It was all in good fun. Clearly a pre-planned bit. And the crowd ate it up. Serena shook Letterman's hand and the two walked away from the scene together, surrounded by late night staffers. All men, everyone was wearing button down shirts. Except, of course, for Serena in her skirt and heels. Keesha points to this era of Serena's fashion journey as being the turning point for Serena style, a moment where she was becoming more comfortable embracing different sides of herself. She was an athlete and a sophisticated woman in her thirties. 


Kesha McLeod: So it's trying to, you know, understanding who you are And she always gets it. And I say amazing part about her. 


Cecil Harris: Shortly after that Letterman appearance, she returned to the 2014 U.S. Open to defend her title. And of course, Serena's on court. Look was as bold as ever. 


Amy Denet Deal: Of course, she's still wearing color and as vivid as possible. 


Cecil Harris: That's Amy, the net deal again, who designed for Serena at Puma. She's looking at the outfits Serena wore throughout the 2014 U.S. Open. It was a hot pink leopard dress by Nike, which she paired with a matching headband. 


Amy Denet Deal: I think that style evolution is that that is I'm looking at just a woman that is absolutely secure and powerful in who she is. That's just who I see. I just see a woman that's just an incredible athlete that still wears what she wants to wear there when she shows up and just beautiful to see her still making those great choices. 


TV Journalist: And here we go in the women's championship of the 2014 U.S. Open, as we've seen with Serena Williams. 


Cecil Harris: When Serena made it to the final at the tournament, she still wore a leopard dress. But this time, it was black and white. 


TV Journalist: And this now. It's a potential moment for serena, her sixth  u.s. open.And her 18th grand slam. 


Cecil Harris: At age 32, she won the U.S. Open again, her 18th major tournament title. And she looked amazing doing it. Amy's career in the sportswear industry spans almost 30 years, and in that time, she says, she's seen a shift. It's a more diverse and inclusive place, especially for women and people of color. And she says that's because of the Williams sisters. 


Amy Denet Deal: How we dress and how we see ourselves as women in the sport. That's up to us now because we had leaders and groundbreakers like these two amazing women that were in tennis that really led the way to that. And they shifted that traditionalism that was there for so long and has something that was youthful and innovative, right, and authentic authenticity of who you are when you play that sport and how you present yourself like that opened the door for women to be more expressive and not have to fit into the norm of the sport. So everybody can have that moment, that moment of being able to express themselves as they play. 


Cecil Harris: Next time on all-American. Serena plays her absolute best. 


Cecil Harris: All American is a production of Witness Docs from Stitcher. This episode was written by Jordan Bell with reporting and production by Albert Chen. Our mix engineer is Casey Holford, who also composed our original music. Our senior producer is Jordan Bell. Our story editor is Johanna Palmer. Our executive producer is Camille Stanley. Extra production support from Norah Richey, Gwen Igor Vega and Manolo Morales. Fact checking by Kelvin Sea Bias. Legal support from Sidney Freeman and Thomas Burke at Davis Wright Tremaine I'm your host, Cecil Harris. Don't forget to subscribe to the show and leave us a review wherever you listen to podcasts. Thanks for listening.