15 Questionable Outfit Choices By Serena Williams

There are few sporting superstars quite like Serena Williams. Look at her list of accomplishments, and you’d have to say that she’s one of, if not the greatest athlete the world has ever seen. Rarely has there been such a dominant force in a sport. Serena Williams is a tennis phenomenon plain and simple. She’s smashed all records, has nothing left to achieve in the game, and very nearly called it quits when she had her baby. But Serena is hungry for more, wants to keep going as long as she can, keep breaking records and wowing audiences. As great as she is, some people weren’t too happy about that, especially the rest of the WTA, as people want to see more competition in the lady’s side of the draw! I could keep praising Serena until the cows come home. It just seems like everything she touches, everything she does turns to gold. But even a woman as great as Serena can look back through her career and pinpoint some regrettable moments. Being a sensational sportswoman, Serena gets scrutinized an awful lot.

Her dress sense has been the subject of plenty of interesting comments, not just from the rest of the sports world, but it must have brought up some interesting conversations, some cringeworthy moments in the Williams’ household. Both Venus and Serena have worn some, let’s say daring, pretty out there, outfits over the years. On some occasions they’ve managed to pull it off, have started a new fashion trend. On others, they must have left the court seriously regretting their choice of outfits. In this article I’m going to focus on the younger Williams sister, look back at 15 times Serena must have seriously regretted her choice of outfit.

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15 Denim And Knee High Boots

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Now, this is an outfit that’s sure to divide opinion. It’s a pretty daring, really out there outfit to wear out on the court. Some would say it’s awful, it would give tennis purists palpitations. But others would say that it’s a super-sultry outfit. The way Serena’s dressed, it almost looks like some type of bondage attire with those knee-high black boots and short tight denim shorts. Then there’s that tight catsuit top, that Nike top outlined with silver studs, that would look in place on the dance floor, but on the tennis court, it’s simply outrageous. Serena loves that top, has worn it many times, so wouldn’t have regretted wearing that. But although she looks amazing, wearing a short denim skirt and knee-high boots on the tennis court? It was a bit over the top and couldn’t have been comfortable either. There’s a reason she ditched the denim soon after that period.

14 A Blue Number

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We all know that Serena Williams has ginormous assets. You can’t really miss them. She knows what she’s got too and regularly flaunts her physique. She can’t really do that on the court. But it’s hard to keep those assets in check. That’s something she’s just not going to do. But looking back at this outfit, even Serena must have been thinking that the top she decided to wear was a little too small for her, a little too tight. Even though everything’s hidden, it shows a lot. It’s probably ridden up her back, but from this image it looks like a short crop top. It’s also not a great color choice when it comes to hiding sweat stains, not that Serena sweats too much about anything.

13 Not Very Practical

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Here’s another pic of Serena wearing those high black boots. Understandably she got a lot of attention during that period, when she frequently wore those boots, that style of attire, even more than usual. This is a pic of her having just stepped foot onto the court, stripping off and getting ready for action. You can see from the crowd’s reactions what sort of an effect Serena had walking onto court in this fashion. People were gasping, just couldn’t take their eyes off her. I’ve mentioned about the black boots already. Serena might be partial to knee-high boots. That jacket is also pretty awesome. But upon reflection, even Serena must have regretted wearing those shorts, those super-short shorts. Playing that match, they became even shorter, kept riding up her legs. They basically became a pair of black knickers.

12 Pretty In Pink

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This is one of Serena’s most outlandish outfits. It’s really out, it’s a fashion statement alright. Again, she loves wearing those super-short shorts. You’ve also probably guessed by now that she loves experimenting and will go out of the ordinary. Going with the pink blazer was an interesting choice for a warm up instead of the typical warm up jacket you'd see in tennis. It’s color coordination at its best, and there’s no doubt about the fact that Serena looks pretty in pink. But even so, in hindsight she probably would’ve gone for a different outfit. Tennis always seems to have the most scrutinizing "fashion police" but Serena tends to own every look she adapts.

11 Green Top

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Serena has worn a lot of tight tops over the years. Well, having said that, most tops are going to be tight on her. This one was super-tight, and also pretty revealing. Most of Serena’s outfits, even the rather outlandish ones, she can pull off. This one though, wasn’t one of her best. The outfit itself isn’t bad, although Serena might regret wearing one that’s not very practical for tennis. But the color green is a color choice that just doesn’t suit her. It doesn’t suit many players. That’s her tight top out of the way. Let’s move onto those super-short shorts. She must have a whole lot of them in her wardrobe. When she decided to wear it for that match, she obviously didn’t anticipate she was going to end up in that position after one of the points.

10 Mid-Serve

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Some of the most unflattering images in tennis are candid shots of players in action, in the heat of battle. This pic isn’t exactly unflattering. But it’s still one that Serena wouldn’t have as part of her tennis photo album. That’s because the majority of people, Serena Williams’ fans, would see this picture and be gawking at one thing, her steamy physique. It was a good decision to wear black by Serena, because it appears to be a very hot and humid night. She wears short shorts anyway, tight tops, but on this occasion, her attire’s clinging to her body tightly, making certain things stand out. We’re all getting quite a sight from this angle, and one can image front on, people would be getting even more of an eyeful.

9 Green And Yellow Puma Outfit

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For someone who’s considered to be a bit of a fashionista, Serena Williams has committed an awful lot of fashion faux pas over the years. In the early 2000s, she had a sponsorship deal with Puma. During her time with the brand, she did wear some awful outfits. I wonder if Puma had a say, or if they were all Serena’s decision? Looking back at those outfits now, Serena would probably put all the blame on Puma, she wouldn’t want to take credit for such an awful design. It looks like a kid’s tennis outfit. It was actually likened to the Cameroon soccer team’s kit at the time. But people were looking too much into it. It was probably just a color combination that was never going to work in the first place on Serena, one that went horribly wrong.

8 Doing The Splits

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This pic just illustrates what a physical specimen Serena Williams is. She’s known for being big and muscular, but that hasn’t hampered her levels of flexibility. Serena looks like she could be a gymnast looking at this position she’s gotten herself in. In this particular case, the outfit isn’t all bad. Again, she’s color coordinated her outfit, and this time around it suits her. But again, it’s those super-short shorts. You’ve probably learned by now that Serena loves those shorts. But they’re not great for situations like this in terms of then riding up her legs. They might as well be knickers, but even Serena wouldn’t go that far. A lot of people would enjoy this sight, but looking back at things, I reckon Serena would’ve liked to have worn a pair of slightly longer shorts.

7 Fashion Mistake At Practice

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It used to be the case that people wouldn’t care what you wear at practice. It’s all about what you bring to the court in the heat of battle that matters. But when you’re someone of the caliber of Serena Williams, people are going to scrutinize you in whatever situation you’re in. A lot of today’s current crop put as much attention into what they wear on the practice court than they do when in a match situation. Serena obviously didn’t put much thought into this outfit. It’s as though she just found those yoga pants lying around and decided to give them a try. It’s not a great look, not a great color or design, and it certainly doesn’t suit Serena. Those Nike yoga pants aren’t one of her best fashion decisions.

6 Serena's Gone Wrong With The Color Choice

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While a lot of tennis players who have sponsors have to make do with what’s given to them, it’s fair to assume that a woman like Serena Williams has a lot of say on the matter. All she needs to say is that she’s not too fond of the outfit, and people will bend over backwards to provide her with one she likes. But for some reason she didn’t feel the need to do that with this bright yellow/green number. It’s not one of her best color choices, and what’s with the blue earrings? Normally she’s quite good at color coordination, but this time around it’s as though her mind was elsewhere. Serena looks like a bodybuilder in a dress in this pic. It’s not a flattering outfit, nor is it a flattering image.

5 An Unnecessary Accessory

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Sometimes players can add a little something to their get up, something that makes them pop a tad, differentiates them from the other players and outfits around them. Serena doesn’t really need to do that. It’s not as if people don’t know who she is. But still, she feels the need to experiment with her outfit. This one is sure to divide opinion. Some may love it, a whole lot of people probably hate it. It’s as though she picked up her Wimbledon outfit and told the clothing manufacturers and designers that she wanted to incorporate some pink in there for the U.S. open. The streaks in her skirt aren’t all bad. But what about those sleeves? Pink sleeves with a white top. I’m no fashion guru but I’m saying that they don’t go. People normally wear those sleeves when they’re injured. Serena thought they’d look good. She got it wrong on this occasion.

4 Blue-Green Outfit

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Some of Serena’s color combinations on this list have just been wrong. But at times they’ve been seriously wrong. This was one of those occasions. As she’s gotten older, her outfits, although some have been wrong, have been more daring, more striking. But back in the day, she was still trying to figure out what worked for her. The only solace for Serena when it comes to this picture is that it isn’t a recent one, isn’t an outfit she’s worn recently. This is a pic from her slightly younger days. Serena wanted to pop a little by wearing this outfit. She pops alright, but for all the wrong reasons That light blue-green outfit just isn’t a color combination that suits her. She’s certainly learnt her lesson.

3 Is This A Rock Concert?

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Even Serena wouldn’t be daring enough to actually wear this outfit during a match. That might be going a little too over the top. Over the years plenty of photographers have gotten Serena on court wearing over the top outfits, tennis racket in hand, in order to take a few snaps of the tennis superstar. This is one of her more bizarre outfits. Serena might have just regretted it. It looks like she was trying to pay some sort of homage to a rock musician, but this just looked very out of place on a tennis court. I don’t think a lot of people would mind, but Serena has shown how creative she can get with outfits and pull something unorthodox off. This just didn't look like it belonged on a tennis court.

2 Latex Pink

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Only the Williams sisters and perhaps Bethanie Mattek-Sands – if you know your tennis you’ll know why – would dream of trying to wear an outfit like this. If the opportunity presented itself, Bethanie would probably wear it out on court during an actual competitive match. Serena wasn’t that brave, wasn’t willing to ridicule herself to that extent. But nevertheless, she did face a lot of ridicule when this picture came out. It’s of course for a photoshoot, and it’s probably one Serena seriously regretted doing. I mean what were people thinking getting Serena dressed head to toe in tight pink latex? In all likelihood the brains of the operation probably had a fetish for that kind of stuff, and just threw a load of money at Serena and invented some kind of marketing campaign so he could create his fantasy.

1 Candid Snap

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For tennis players, candid snaps of them mid-shot are always the worst. They come up with all kinds of funny facial expressions, and that’s something the camera’s just love to capture. This is something of a funny facial expression by Serena, but most people would look at this pic and comment on her choice of outfit. Firstly, that green-orange combo isn’t the best creation by Nike’s designers. Secondly, as you’ll know by now, Serena loves to wear super-short shorts. She loves showing off a whole lot of leg. Due to the color of those garments, some people might be thinking they can see a whole lot of something else. Incidentally she was also giving those behind her a proper eyeful during that match against Maria Sharapova.

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