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Serena Williams Star in First Fashion Show

Women with larger busts know the legitimate struggle that comes with finding a really good sports bra. And it’s not just about getting your breasts into the bra, which is a battle in and of itself:

 

We have to consider how the bra will support the weight of our chests, how the straps sit and feel (think about the long-distance runner who has a litany of scars from sports-bras past that weren’t the perfect fit), and a slew of other woes we needn’t bore you with.

Serena Williams and Olympia pic

And once you’ve actually found a bra that feels good, the next step is figuring out how you feel in the bra and if you like the look of it.

After working with the tennis champ for almost eight years, celebrity stylist Kesha McLeod knows how to translate Williams’ daring style off the court. Here, she looks back on the outfits that were total grand slams.

August 2016

Serena loves to be “very daring and risky,” says stylist Kesha McLeod, and she feels most confident in “high-waisted pencil skirts,” which is evident from the bold bra-top look she wore to the Berlei Sports Bra launch.

Serena Williams No Makeup

June 2016

At the premiere of her documentary, Serena, her stylist McLeod said the star wanted to look “outstanding” — which she definitey accomplished in this sparkly LaQuan Smith gown.

Serena Williams Best Red carpet Photo

“This was her time. Anna Wintour approved this dress,” she said. “We wanted the slit to be so far up that it looked like she didn’t have underwear on, but she did!”

February 2016

Serena’s see-through lace custom Galia Lahav gown at Vanity Fair‘s Oscars after party marked one of her biggest fashion risks, says McLeod.

Serena Williams No Makeup

“The flesh tone in the mesh had to look naked, so that was a very scary moment up until the last hour,” she said. “With the perfection of the fit and having an awesome tailor out in LA, it was one of my favorite moments on her.”

December 2015

To be presented with Sports Illustrated‘s Athlete of the Year award, her stylist worked with the designer for Williams’ HSN line months in advance.

Serena Williams Best Red carpet

“Serena was like, ‘I just want a super sexy moment,'” McLeod said. Christian Louboutin even custom-made her Swarovski-encrusted heels for the occasion.

November 2015

After a last minute change, Williams wore this cinched-in sheer Gucci dress over a Wolford bodysuit. “Belts are always her thing.

Serena Williams Best Red carpet

We usually argue back and forth about where and when a belt is appropriate,” McLeod said. “And that belt is mine! I took it off and she kept it.”

February 2015

McLeod wanted to “bring out ” Angelina Jolie when she put Williams in this sexy, high-slit red Ines Di Santo gown at the Vanity Fair after party.

Serena Williams Best Red carpet

“Little do people know, we will do a heel for the red carpet [she wore Giuseppe Zanottis from her closet, here] and change into a flat right after,” McLeod told PeopleStyle. “Some women need heels to feel confident. She doesn’t.”

August 2014

“This is the start of her confidence and where the Serena vibe kind of took off,” McLeod said.

Serena Williams Best Red carpet

The stylist paired high-low here on The Late Show With David Letterman, with a crop top/skirt combo from TopShop and Balmain heels.

March 2014

The tennis star loves this look so much, she actually still uses it as the screensaver on her phone. But it almost wasn’t perfect.

Serena Williams Best Red carpet pic

“This is the craziest story: Right before we figured out how to get the sheer moment perfected, we didn’t get [the sheerness] right, so I found dark foundation and dabbed it in between up until the red carpet just to make sure those sheer [parts] stayed chocolate brown,” McLeod shares.

August 2012

One of Serena’s go-to designers for talk show appearances (as on The Late Show With David Letterman here) is Victoria Beckham, because the dresses don’t require tailoring.

Serena Williams Best Red carpet picx

“Victoria responded on Twitter to Serena [about] how beautiful she looked and how [she] makes dresses specifically for women like [Serena]. It was a really good viral moment for us,” McLeod said.

February 2011

“Our first Vanity Fair together!” McLeod said of Williams’ coral Ines Di Santo gown. Getting the look right took more than five fittings, especially to nail down the interior stucture of it.

Serena Williams Best Red carpet

“Under that dress she is wearing flats and a boot, because she had surgery on her toe,” she said. “It’s mesh tulle that was underneath to keep it open for her boot.”

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