Serena Williams' Stylist Dishes On Her Maternity Style

Photo: John Shearer/Getty Images.
One of the highlights of the Met Gala earlier this month was, undoubtedly, Serena Williams making her first red carpet appearance since announcing she was pregnant. The tennis icon looked resplendent in emerald satin Versace, and ever since then, we've been eager to see what would come next in terms of Williams' maternity style. So, we rang up stylist Kesha McLeod, who's been working with the 35-year-old for over seven years, for some intel on what to expect from her fashion choices in the months to come.
In addition to working with one of the greatest athletes of all time, McLeod has a roster of major NBA players, including Chris Bosh (Miami Heat), Andre Iguodala (Golden State Warriors), and Serge Ibaka (Toronto Raptors). And though she's staying mum — for now — about any specific looks that Williams could be wearing on forthcoming red carpets, she did let us know that the green Versace number was basically a Serena-Donatella collaboration, and we're primed for some more major designer maternity fashion moments in her future. (She also hinted at the prospect of custom Michael Kors or Stella McCartney, so fingers crossed!).
Below, McLeod fills us in on what it's been like to dress Williams for nearly a decade; plus, click on to get the stylist's scoop on five of her favorite looks from the star.
How did you get in touch with Serena?
“We got connected through another stylist who had a heavy workload, and I was free at the time, so I dressed Serena for a Super Bowl event. That year, she did commercials, and she was in Vanity Fair for the first time in awhile. It was after she was injured — she was out [of playing professionally] for a year and a half — so I was styling her with a cast on her leg.”
What were your creative workarounds for styling a cast?
“I put her in a lot of formfitting dresses with fishtail hems, or some kind of slit at the bottom, because she had a bedazzled cast. I had to make sure people could see that. Then, I’d carry her flats with me so she could put them on when I needed them."
How has the world’s reception to Serena changed since you began working together in 2010?
“It’s very different now! Right after that Vogue cover in 2015, that’s when people really took notice — the pulls and fittings were different. Vogue is that stamp of approval; it's how you know you've arrived. There’s more of an appreciation of who you are [fashion-wise] after Vogue— even though I’ve always thought of her as this alpha-female. She’s Serena Williams! Over time, yes, the fashion brands she wears have changed; it’s more elevated now. She takes more risks, and she trusts me and takes my opinions a little bit more."
How would you say Serena's style has evolved over time?
"She used to wear nothing that really flattered her shape; you might’ve seen her in a few asymmetrical dresses in the past, or certain halters that accentuate her shoulders too much. She completely dominates the courts, but I wanted to pull out her softer, more feminine side — it was about finding that side of Serena that people don’t normally see, while still having her exude enormous confidence.”
Do you style pro athletes any differently than non-athletes?
"I keep in mind that when they’re not ‘performing,’ they need to look like regular people. Their muscles aren’t super flexed or tight — you need to bring out their relatable side, and I’m very conscious of that. Because who we know is who we see on the court when they’re playing — and I try to show a side of a client that no one knows."
What are some of the main designers you’ve dressed her in over the years?
“Michael Kors, Ralph Lauren, Tibi, Cushnie et Ochs, Jonathan Simkhai, Burberry — Christopher [Bailey]. And Dolce & Gabbana, too — she wore Dolce a lot when I first started working with her. A.L.C. is great for basics for her. Gucci always looks really amazing on her. She’s worn a lot of Vera [Wang], too, Vera has come to see her at the US Open, and Vera always made sure Serena sits front and center at her show. We love DVF, too — her wrap dresses are just beyond. Jimmy Choo, Giuseppe Zanotti, and Louis Vuitton are my staple shoe brands to put her in. And also, she's now wearing Gianvito Rossi, too; it's like she doesn’t want to wear anything else!”
How did you approach Serena’s first red carpet while pregnant, for the Met Gala?
"It was a super-complicated, beautiful gown with a long train. Since it was such an avant-garde theme this year, Serena’s belly basically was the avant-garde element; it was a defining fashion moment for Serena. Versace sketched the dress, based on Serena’s thoughts — she definitely had a lot of input what she was wearing. She’s really into fashion and she gets it. She understands seam allowances, and how much to take in from here or there; she has ideas about what specific fabric to add, and whether a piece should have a hook-and-eye closure or not. So she actually plays a huge role in what she wears. I basically styled the full look and made sure everything went together with the dress, but that woman and Donatella Versace — they really did everything!”
Did Serena work with Donatella directly on the look?
“Yes, Serena went to Milan last September; for some reason I couldn’t go, because there was a scheduling conflict, but when she went to Milan, Donatella gifted her an entire wardrobe of what had just came off the runway. Serena came home and I saw her closet, and I was like, ‘Where did you get all of these Versace pieces from?!’ and she was like, ‘Donatella!’ Versace exudes femininity, Miami, and fun, and Donatella just loves, loves, loves Serena.”
What other designers can we expect to see Serena wear during her pregnancy?
“The designers will always be a surprise! Now, they’re not just designing a dress for her as a celebrity; the focus is now on showing that baby bump. Women usually throw on big, oversized dresses or the caftan. As Serena’s Met Gala dress showed, you can still wear a full-on gown, with a long train. I’m excited to see what designers will come up with. This is my second pregnant client I’ve worked with, and it’s really not any harder to dress [than non-pregnant clients].
"You’d only know Serena is pregnant from the front, so far. She’s a little smaller up top now, because she’s not swinging her racket. Now, we’re doing more cinching around the hips and higher empire waists. And there are so many possibilities about what can be done as custom designs; who would've known Versace, out of all the designs out there, would make a dress for a five-months-pregnant woman? Once you open up that conversation around custom design, the possibilities are endless."
Beyond the step-and-repeat, how are you dressing Serena in day-to-day?
“She’s still going to be, and look like, Serena Willams, and she’s still in regular pieces all day long accentuate baby bump. It’s a lot of Helmut Lang, Theory, and H&M’s organic cotton tees. Serena has her own line, too — Serena Statement, which is also where a lot of her basic pieces that she wears are from. She just wants something simple, easy to throw on, that works for meetings, too — nothing super complicated. We might pair a pencil skirt with a T-shirt, and throw a Burberry trench with the sleeves rolled up over that.”
How is your job different — or more challenging — when you’re working with a pregnant client?
“I don’t have kids myself, but from being around and working with pregnant women, I know that sometimes they get so tired and have low energy levels, so they don’t want to try anything on. That’s when I have to get creative. Maybe that involves a cape over a sundress, or a sleeveless jacket. High-waist pencil skirts are really good, too. A lot of pregnant women don’t want to wear pants, and they often don’t want to wear maternity. That’s what I’ve learned — they still want to wear regular clothes. So tailoring needs to happen. You have to still create looks that make them feel like themselves. Around four to five months in, the baby drops and you start to show; that’s where Serena is right now. Right now, I’m not putting Serena in maternity clothes, but give it some time — by the seven- or eight-month-mark, everyone is like ‘Give me a maternity dress’!"
Where have you been sourcing Serena's swimwear while pregnant? That one-piece she wore for her (accidental) reveal went viral...
“Because Serena is in Miami, she shops for swimwear all the time. She has a swimwear closet! Everything still fits the same; only the tops are different size-wise. The suit she wore for her reveal, it was a regular, non-maternity swimsuit that she already had [pre-pregnancy]. That was a custom color, but now that suit is sold out in all colors — you can only get it custom-made.”
Are there any trends you're planning to get Serena into next?
"I'm really into the trench-coat-as-dress idea, which really showcases her beautiful long legs. I also like showing off her back and shoulders, since her muscles are sculpted differently because she's not playing currently. It's like I'm dressing a whole new physique; a whole new body. It's fun!"
Have you started styling Serena's future child's wardrobe yet?
"Not at all! I don't even know what she's having [gender-wise] to prep. Little funny, comical onesies is what I'll be getting."

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