Fashion Files: Maria Sharapova

Maria Sharapova often incorporates relevant fashion elements into her on-court fashion, like the collar on her night dress at the 2010 U.S. Open. (Carlos Saavedra/SI)

Welcome to the Fashion Files, where we track the style evolution of tennis’ biggest stars. In our second installment (check out Rafael Nadal's fashion files), Courtney Nguyen and Erwin Ong, a freelance content producer for tennis, sports fashion and Los Angeles lifestyle, dissect Maria Sharapova's outfits over the last decade.

The current world No. 9 is all about her dresses, and thanks to her fashion roots, she often puts a stylishly modern twist on them. More recently, Nike has toned down her kits to make them more marketable to the public, but that hasn't made them any less memorable. Click here to see more of Sharapova's best and worst on-court outfits. 

SI.com: What's your overall take on Maria's status in tennis as an on-court style icon?

Ong: Maria knows what she likes to wear and seems to have chosen a path that reflects this. It shows in the confidence she has when wearing her outfits. I don't think she immediately comes to mind when the public thinks about tennis fashion (in the same way that Rafael Nadal's capris, Serena Williams' catsuit or Bethanie Mattek-Sand's flamboyant style comes to mind), but her connection to the fashion world gives her that insider edge. Her clothes can be polarizing, but that's what happens when a risk-taker does her thing.

SI.com: How has Maria's style evolved over the years?

Ong: Her style has matured as she has gotten older, and she has developed a vision for what she likes to wear. Mostly dresses, halters and racerbacks -- styles that don't cover up her arms and shoulders. She knows what she likes and what works for her body. Probably for business reasons, she and Nike have toned down her style in order to line up her match outfits with what's available for sale (i.e., the Maria Sharapova collection). Gone are the days of one-of-a-kind dresses created solely to generate buzz. Now it's all about what you see on Maria is what you can get at your retailer.

SI.com: Which dress/kit do you think was her most iconic look?

Ong: The 2006 U.S. Open little black dress is what cemented it for her. To have it be THAT dress, in New York City, at that time of year (i.e., close to fashion week), and as a Grand Slam winner -- it all came together at that point. This is the closest any WTAer has gotten to turning the classic LBD into a classic on-court outfit.

Maria Sharapova's black dress for the 2006 U.S. Open is reminiscent of Audrey Hepburn's Breakfast at Tiffany's dress. (Bob Martin/SI)

SI.com: Favorite look?

Ong: If I had to pick, the 2008 French Open was my favorite. The '20s-inspired dress, the back of which was adorned with a pearl-button closure, marked the beginning of Maria's partnership with Tiffany & Co. She also wore Tiffany earrings for the first time. The outfit came with a navy blue cape windbreaker (which we were sad to find out was a one-off). The hemline and the slit on that 2004 Wimbledon dress makes it a close second.

SI.com: Yes, this is my favorite dress of the last 10 years worn by anyone. It was so simple and classic, and the blue stood out beautifully against the red clay. The fact that she would wear such a classy dress while cursing at the French fans made me love it even more.

Maria Sharapova's navy dress at the 2008 French Open was a universal favorite. (Bob Martin/SI)

SI.com: Least-favorite look?

Ong: My least favorite was 2007 French Open, when she really started going for her outfits. The top looked overwhelming and seemed to restrict her movement. The waistline also gave her a weird proportion when she was wearing it both with the pants and without.

SI.com: I didn't mind the dress, but the over-the-top embellishment on the visor disrupted the whole look.

Maria Sharapova wore pants under her 2007 French Open dress in the early rounds of the tournament. (Clive Brunskill, Clive Rose / Getty Images)

SI.com: Where would you like to see her go with her style?

Ong: I like the trajectory. Could she help innovate shoes, perhaps? Is there a way to make them look less utilitarian?

Here's a look at Sharapova's on-court outfits through the years, with comments from Ong and Nguyen.

2004 Wimbledon

And so it begins. The Wimbledon dress to end all Wimbledon dresses. -- Nguyen

This is the dress, right? And really, this is one of the first that caught my eye (perhaps after Venus Williams collaborated with Diane von Furstenberg on that corseted Reebok dress the year before). Sharapova's Nike dress struck a balance -- femininity, class, simplicity. Someone should be wearing a version of this dress every grass season. -- Ong (Photo: Simon Bruty/SI)

2007 Wimbledon

Here's a brief exchange that Maria had in a press conference about her dress:

Q. What about your outfit here at Wimbledon this year? Anything special about it?

SHARAPOVA: Yeah, it's Swan Lake inspired.

Q. I have no clue what that means.

SHARAPOVA: When you see it, you'll see a swan. You'll be inspired. My coach saw it the other day and he said he started feeding bread to it, so he got it (smiling).

(Photo: Bob Martin/SI)

2007 U.S. Open

THE SHEER SLEEVES ON THAT JACKET! This dress was inspired by New York and featured an abstracted version of the city skyline laid on on her chest in 600 Swarovski crystals. It’s the first red dress Maria wore as a pro. -- Ong (Photos: Elsa/Getty Images)

2007 WTA Championships

I call this her "sexy librarian" look (bow collar blouse). -- Ong

I call this her "let's pretend this kit never happened" look. -- Nguyen (Photo: Jasper Juinen/Getty Images)

2008 Wimbledon

It's fun to see Sharapova -- inspired by London's history of bespoke tailoring -- and her sheer racerback-top-turned-tuxedo (the return of the pleats!) with a bib front. Her low-rise shorts have a wide-tailored waistband (with tab closure), pinstripes and gold-stitched buttons. She also had a single-breasted warm-up blazer with gold stitching. There was also a pair of warm-up trousers, but they did not make an appearance on the court. This is one of the few instances that Maria's worn shorts (that I can remember), and it's a great look to see done with tailored shorts. -- Ong

Sharapova lost to Alla Kudryavtseva 6-2, 6-4 in the second round, and Kudryavtseva admitted that she didn't like Sharapova's outfit. I remember thinking that I would have spent more time ripping this pretentious and cloying kit apart ... except it was short-lived because of her early loss, and this stuck around for much longer. -- Nguyen (Photos: Clive Brunskill/Getty Images)

2009 French Open

This layered blue dress actually looked wonderful in repose -- one of our favorites -- but it looked like a mess in action. Extra points for the cropped warm-up blazer that came with the outfit. -- Ong

I remember this dress photographing really well on non-windy days. But you're right, most of the time Maria looked like she was fighting off a billowy parachute. -- Nguyen (Photo: Bob Martin/SI)

2009 U.S. Open

The asymmetric silver lines (and a mesh cut-out) on this U.S. Open evening dress (the day version was in lilac and lime green) came with earrings designed by Frank Gehry for Tiffany & Co (worn as part of Sharapova's partnership with the jewelry retailer). -- Ong

When Sharapova doesn't wear a visor, I lose my tennis bearings. When she opts for the Karate Kid headband, I lose my interest. -- Nguyen (Photo: Emmanuel Dunand/AFP/Getty Images)

2010 Australian Open

The print mesh overlay on this Australian Open dress garnered a lot of reaction from the peanut gallery. This was one of her more fun Melbourne kits, and also notable as the first of the Maria Sharapova collection, worn by her and Kai-Chen Chang, Julia Goerges, Anastasia Pivovarova and Madison Keys. Also, this design was plucked from her sketchbook one year prior. -- Ong

I enjoyed the dress more than the movie it seemed to be based on. -- Nguyen  (Photo: William West/AFP/Getty Images)

Click here to see more of Maria Sharapova's best and worst on-court outfits.