"I have been watching you play tennis since you were a teenager," Anna Wintour said at the beginning of her conversation with Serena Williams at Spring Studios, where the athlete would be presenting her Spring 2020 see now, buy now collection for her line, S by Serena. "It's taken so much hard work and dedication, and you're certainly one of the world's greatest and most successful athletes," she continued, before asking: "What on Earth makes you want to take on fashion?"
Williams is indeed best known for the sport she's been playing (and dominating) since the '90s, but she reminded the audience that fashion has been a longtime love and ambition of hers as well. "I went to fashion school, I like to say, between winning Wimbledons and U.S. Opens," she told the crowd of editors, designers and other influential figures in the industry gathered to hear Wintour and Williams speak on Wednesday morning. "It was a natural step for me — I didn't even think about it. I was like, 'I'm going to fashion school, I'm going to art school. I know that's what I want to do.' And now I'm here."
Williams explained that she wanted to change up the format for her S by Serena collection reveal — she hosted a runway show last season that was attended by Wintour, Ashley Graham and Kim Kardashian West — because she wanted the opportunity to speak to her technical background in design and her longtime love of fashion. After she and the legendary Vogue editor finished their talk, models emerged wearing the Spring 2020 collection, which was inspired by travel: easy separates that can be worn together in various ways, giraffe prints, vegan leather, sequined pieces with cut-outs.
The wide-ranging conversation covered everything from Williams's much talked-about tennis outfits to the nails at the 2020 Oscars (because "they were so much better than the dresses," Wintour said) to the various the athlete-designer-mother-entrepreneur wears. Ahead, read some of the highlights from Williams.
On her on-court fashion
"I'm trying things out — sometimes, they are a miss. But that's okay. I think it's so fun, to have fun with fashion. In my sport, I have a great opportunity to play in something really wild and really fun, and really express myself. Sometimes, people only see me on the court. That's where I'm like, 'This is me. I love fashion. This is what I want to do. This is how I want to express myself.' A lot of those times, I'm in the room with designers and they've given me incredible experience, working with Nike and other companies — if you look at a company like Nike, they're the best at what they do. To be able to work with their designers and to understand how they create something has been able to help me with my brand."
On Serena Ventures
"I started in 2014 and then, around 2016, I learned that less than 2% of companies that were venture-backed were [run by women] — I thought, 'That can't be true. 98% goes to men? That's not even a real number.' Minorities, even less. So I said, 'You know what, this is my calling.' So Serena Ventures, we started backing a lot of companies, female-owned companies. We believe in brands and people. When we back people, we really back the founder — we obviously love the product, but we really need to love the founder. That means a lot to us. Our portfolio has men, it has women, it has minorities. We just want a diverse portfolio… For me it's all about creating that message of inclusivity. And inclusivity is everyone."
On cultivating an authentic brand on social media
"With social media — us in particular — we put a lot of our time behind people really seeing what the brand is about, how people from everyday walks can look in the brand, how they can represent it. My family, they do it because I’m like, 'You guys have to do it, there's no other option. I need you guys here.' And they come through every single time and it's really amazing. But it's also a different way for marketing. Marketing, I feel, with the new age of technology, has to change at some point. Having a direct-to-consumer company, you have to find different ways to market and to find that customer and to reach that customer because the customer is changing. As a company, we want to be able to change with the customer."
On her heroes
"My heroes have changed. I always looked at different people. And after having a child, I was like, 'My heroes are moms.' Women are superheroes. To have a baby and have to go to work two weeks later, or three weeks later, or even to go work from 9 to 5 — I don't do that. I'm really fortunate where I'll wake up early at 7, I'll work until 10 or 11, then I'll have the rest of the day with my daughter. I'm so lost for words when I think of these women who spend day in day out helping and providing for their family and really doing it, when I know how hard it is for me to leave my daughter. I'd never felt that way before, until I became a mom. I think women need to be recognized."
On the advice she'd give her younger self
"It takes a lot of work, in everything that you do. It takes a lot of work and dedication. I know that sounds classic and redundant, but it's true. I can't stress that enough. There's [that saying], the 100,000 hours you have to do. I took that for me to be the best tennis player in the world. I have been doing fashion since 2000. That's when I went to school. I've been doing this a really long time — more than people actually realize, which is why I think it was important for me to sit down and have this different format of a fashion show. It takes a lot of time and dedication Some things at some companies might pop overnight, but that's such a small percentage. Nothing can replace hard work."
On her all-time favorite tennis look
"I thought about that and I was thinking, immediately, of the jean skirt that I wore in 2004 with the high boots. Then I was like, 'That's a lot, because my favorite things in life are tutus.' So the tutu look with Virgil [Abloh from Off-White]. I kept all those dresses and sometimes I wear them."