Stephanie McMahon is the most powerful woman in WWE. As the only daughter of WWE Chairman, Vince McMahon, Stephanie has lived most of her life in the spotlight since she has grown up on WWE TV and even went on to marry her on-screen husband Triple H. The couple has been part of storylines together for more than a decade and outside of the ring, they have created a family for themselves and are the parents of three daughters. Stephanie is like superwoman and manages to juggle life being a mum, a business owner, and someone who is often seen as a villain on WWE TV. It is sometimes hard to believe that she is able to do so much.
Despite all of her power, Stephanie is often needed on WWE TV, which is where she is seen as one of the authority figures, serving as the current Commissioner of Monday Night Raw. The billion dollar princess is a former women's champion so she knows how to handle herself in the ring as well. It's just a shame that she doesn't always wear the most flattering outfits.
The following list will look at 15 of the worst fashion choices that Stephanie McMahon has ever made both on-screen and off-screen. Apparently, being the most powerful woman in the wrestling business didn't come with its own stylist to ensure that she was never part of some of these material mishaps.
15 The Red Raw Dress
Stephanie was revealed as the Commissioner of Monday Night Raw back in 2016, just ahead of the WWE draft in July. As part of SmackDown Live, Stephanie and her brother Shane were able to choose superstars that they wanted to represent their respective brands moving forward.
Stephanie was seen in this dress, which many fans thought was a little too much, even for her.
She has been called a mark for herself a number of times or a mark for her husband but wearing a dress with the Raw logo all over it was too much. Steph could have just worn a red dress to show her allegiance to her brand but that wasn't enough to ensure that the whole world would be talking about her the next day. Luckily, she hasn't been seen in the dress since but she's remained the Commissioner of Raw for the past two years.
14 The Surprising WrestleMania Outfit
Many fans of Stephanie will remember some of the absolutely shocking wardrobe choices that she made earlier in her career. The above is one that probably stands out the most, as she tries to make this outfit work as part of WrestleMania 32 when she accompanied her husband Triple H to the ring for his match against Roman Reigns. Stephanie was speared as part of this match and the outfit just made the segment so much worse.
Stephanie has never been like all the other women in WWE. Showing off her stomach wasn't something that she wanted to do. Instead, she came up with innovative ways to show off her figure.
This was definitely one of the worst outfit choices of her career. Back in the late '90s and early '00s, what was deemed acceptable was very different than what we feel is in style now, which is why Steph thought that this was a good fashion choice.
13 The Long Leather Suit
Being the Commissioner of Monday Night Raw comes with a number of perks, which means that Steph is able to always dress however she wants, typically making quite the entrance with her catchy theme. This issue is that Stephanie isn't told how to dress by anyone and her employees are afraid to tell her that she doesn't look great. This means that no one will warn her if she is dressed badly.
This was apparently one of the outfits that made it through the curtain over the past year, as Stephanie is seen wearing what looks like a long, black leather jacket that has been zipped all the way up. It is thought that this outfit should have been worn with trousers and not as a single piece, since it definitely doesn't do Steph's incredible figure justice and just makes her look as though she forgot to take her coat off backstage.
12 This Unflattering Grey Dress
It's strange seeing Steph go from a "yummy mummy" when she's on WWE TV into someone completely different when the cameras are turned off. Her revealing outfits are saved for when she's on national television since she decides to dress much more like a mother when she is spotted out in public.
Steph is spotted here in ankle boots wearing an extremely unflattering long grey dress and a leather jacket. Steph definitely has a love of leather, something that you will probably discover throughout this list. Leather or PVC is always her go-to fashion choice, which could be why there have been so many bad outfit choices from the billion dollar princess over the past two decades. Steph is 41 years old and has been on WWE TV since she was a teenager, literally growing up in front of our eyes, so it is only natural that her sense of style has changed over the years.
11 The Leather One-Shouldered Dress
The former women's champion has been on WWE TV for more than two decades, which means that there are still images of her online from the late '90s.
These images show that her fashion sense early on in her career was something that even she would be embarrassed about if she looked back at some of these photos.
This leather dress was definitely one of her worst decisions. Steph had injured her neck at this point and was able to get a neck brace that matched the dress, but this just manages to make the entire outfit event tackier than it would have been if the neck brace was a normal white color.
10 The Shapeless Pink Dress
Stephanie is someone who prides herself on the fact that she is still in incredible shape for her age. She is a mother of three and still looks better than many of the women who are half her age and wrestling with the company. For someone who is addicted to late-night workouts and eating as healthy as possible, Steph isn't someone who learned how to dress so that she can show off her toned figure.
The former champion is pictured above wearing a dress that is basically shapeless and unable to show off her hard work.
Steph is popular with the WWE Universe and many fans have been quite forthcoming about the fact that they are still attracted to the boss' daughter but that she makes it difficult when she dresses in frumpy, horribly-colored dresses like this one.
9 The Infamous Blue Leather WrestleMania 18 Outfit
It's been 16 years since Stephanie McMahon walked down the aisle at WrestleMania 18 wearing this metallic blue jumpsuit and it looks to be just as bad of a decision today as it was back then.
Stephanie was always a better host than a wrestler so it is unknown why she felt the need to dress this way. Steph accompanied Chris Jericho to the ring for his match against Triple H, where she attempted to aid him a number of times. The biggest issue with the outfit is the color. It just doesn't seem as though it is something that someone with Steph's stature should be wearing at one of the biggest events of the year. Now, it will be immortalized forever on DVD. It is interesting to note that this outfit has since been auctioned off online.
8 The Casual Dress With Knee-High Boots
Sometimes it seems as though Stephanie forgets that she is supposed to be the authority figure on Monday Night Raw because she is happy dressing like she is one of the superstars. Steph hasn't wrestled in almost four years and even then, it was only as part of one match because WWE was booked into a corner.
The wife of Triple H has become an iconic figure on WWE TV over the past few years but sometimes she forgets to dress like the businesswoman that she actually is. Knee-high boots and a patterned dress don't seem like the right kind of outfit choice for someone who is supposed to be calling all the shots. This looks more like an outfit that one of the current women's wrestlers would wear on their day off. They say that you should always dress for the job you want but Steph needs to start dressing for the job that she actually has.
7 The Stephanie Vs. Ronda Outfit
Stephanie McMahon and Ronda Rousey faced off in a mixed tag match at WrestleMania 34 earlier this month, in a match that also included Kurt Angle and Triple H. Ahead of the match Stephanie and Ronda were part of a number of segments on Monday Night Raw, including one where Ronda attacked Steph and delivered a Samoan Drop.
McMahon would have known that she was going to be getting physical as part of the segment and that she needed to ensure she was wearing clothes that she knew she could wrestle in, but this shapeless jumper, jeans, and knee-high brown boots were bad choices. It also seems that she decided to change up her hair for this segment as well, but it just ended up adding to how bad the outfit actually was overall.
6 The Little Red Dress
Stephanie McMahon made a number of mistakes throughout 2014, including when she decided to step into a feud with former Divas Champion, Brie Bella, and her husband, Daniel Bryan. Of course, Bryan wasn't forced to retire from the company until two years later and he did manage to defeat her husband at WrestleMania and later. He became the world champion, which meant that Steph was on the losing side of the entire rivalry.
The actual storyline wasn't her only mistake since her dress was pretty bad too. The above image is from when Stephanie was arrested on Monday Night Raw for slapping Brie Bella. It definitely isn't one of the most flattering images of the billion dollar princess and this likely won't be a dress that she will be wearing on national TV again anytime soon.
5 The Zip-Up Leather Dress
Leather hasn't been something that is in fashion for a very long time but Stephanie is someone who has been able to bring it to the forefront of people's minds throughout her career as one of the authority figures on Raw. Above, she is shown once again appearing as the Commissioner of Monday Night Raw, wearing a dress that doesn't seem as though it was a good idea for her. This dress is much longer than anything Stephanie has ever been seen in and it looks like it has no shape.
The leather is something that Steph likes to wear, but she hasn't been able to actually make it work, despite how much she has tried to push it forward.
Luckily, this wasn't a lengthy segment so Steph wasn't on TV for too long, meaning the WWE Universe wasn't fully able to voice their opinion on the outfit.
4 The Summery Shorts
Stephanie is a villain on WWE TV, which she has become very good at because she has been in the business for so long. She doesn't have to care about what anyone else thinks since she is one of the biggest villains and most powerful people.
This means that when Stephanie appears on WWE TV, she regularly shows up in some outfits that are pretty out there.
Of course, the former women's champion often shows off her work out sessions on Instagram and shows that there is a reason she is in such good shape. Who can blame her for always wanting to show off her toned legs and incredible figure? She's a mother of three who looks like she is in incredible shape, which could be why she feels like these kinds of outfits are appropriate for national TV.
3 The Cowboy Boots
Stephanie's outfit choices on WWE TV over the past few years have definitely been a topic of conversation with the WWE Universe. Back in 2014, Steph showed off the fact that she doesn't have to answer to anyone when it comes to her outfit choices when she showed off her cowboy boots and a pair of leather black shorts.
Steph was part of The Authority at this point in her wrestling career and as a heel, she enjoyed dressing in unusual ways because it gave the WWE Universe the bait to give her the heat that she needed.
Steph's sense of style has been something that many of the WWE Universe have commented on but because of her position and the power that she currently has, it seems that the boss' daughter doesn't actually care about anyone else's opinion when it comes to her fashion choices.
2 The Seth Rollins Outfit
At The Mae Young Classic last year, Stephanie was in attendance to promote the fact that this was a huge night for women's wrestling and dressed up for the occasion. A few hours earlier, she was at SmackDown Live when her father was attacked by Kevin Owens and came out to help him.
This was when the WWE Universe saw her outfit and made the decision that Steph had decided to come as a cosplay of former WWE Champion and one-time Authority member, Seth Rollins. Let's be honest, the outfit doesn't look flattering in the slightest. It is unknown what kind of look she was even going for by choosing this. A normal straightforward black dress could have easily done the trick and saved her a lot of abuse online but Stephanie isn't the kind of woman who would be happy blending into the background.
1 The Little Blue Dress
Every WWE fan will remember Payback in 2014 as the event where Stephanie McMahon attempted to force Daniel Bryan to relinquish his world championship, threatening to fire his wife Brie. Instead, Brie slapped Stephanie and declared that she quit the company to save her husband's title reign. Stephanie was then forced to exit the ring after her plan had failed.
Stephanie came to the ring in a tight, blue dress that obviously reflected the light, which is something that she would later live to regret. When she ran from the ring after Brie had slapped her, there were images of Stephanie's dress that made it look as though she had a little accident. It could have been the lighting in the arena or Steph could have actually had an accident. All that is known is that this is an embarrassing situation that she has had to live with ever since.