5 Best Looks Of Stephanie McMahon's Career (& The 5 Worst)

Stephanie McMahon, the daughter of Vince McMahon, is born with wrestling in her gene, as she has been part of her father's empire from childhood. The Billion Dollar Princess has been on TV for over two decades, participating in various incredible story lines, especially as a heel. Even today, she creates nuclear heat with her character.

As look plays an important role in professional wrestling, Stephanie has experimented with looks from the early days of her career. Whether in the wrestling gear or the corporate attire, Stephanie has always looked flawless on TV.

This article takes a look at five best looks of Stephanie McMahon's career and five worst.

10 Best: The Wedding Attire

Stephanie McMahon was scheduled to marry Triple H on an episode of RAW in 2002. While they got married in real life eventually, the on-screen marriage didn't have a happy ending because Triple H embarrassed Stephanie in front of the WWE Universe. Also, he assaulted Vince McMahon after canceling the wedding. Although the wedding was catastrophic, Stephanie looked stunning in the wedding dress. Wearing a beautiful wedding gown, she stole the segment.

9 Worst: The Dark Wedding Attire

When Stephanie McMahon made her on-screen debut, she was an innocuous and jovial daughter of Vince McMahon. As a matter of fact, she was not a heel at the beginning of her career. As Vince was having a rivalry with The Undertaker, the latter was obsessed with Vince's young daughter, Stephanie.

Undertaker's fixation with Stephanie went too far, and The Ministry of Darkness wanted to tie the knot with her, which was subsequently ruined by Stone Cold Steve Austin. Nevertheless, Stephanie was a novice in wrestling business back then, and her outfit was substandard for that segment.

8 Best: WrestleMania 32

Triple H gave some memorable entrances at the Showcase of Immortals, and Stephanie was part of a couple of them, including at WrestleMania 32, where The Game had produced one of the best entrances of his career. Stephanie also accompanied him, as the WWE Championship match mainevented the show.

Stephanie looked great in a high heel boot and a black jacket. Her curly hairstyle made her look like an unerring heel.

7 Worst: The RAW Logo Printed Dress

When the brand split was reintroduced in 2016, Stephanie got the charge of RAW, while Shane McMahon had the responsibility of handling RAW. Therefore, the siblings chose their preferred Superstars for their respective brands.

To show the support for the red brand, Stephanie wore a red dress with 'RAW' printed all over it. The dress didn't really suit the class of the Billion Dollar Princess, and it was arguably one of the worst looks of her career.

6 Best: WrestleMania 34

Stephanie McMahon had participated in several big events, including WrestleMania. Her last match was at WrestleMania 34, where wrestled with Triple H in a Mixed Tag Team match. The power couple of WWE faced Kurt Angle and Ronda Rousey, who also made her debut in that match.

Although she tapped out to Ronda's arm bar, Stephanie's outfit was on the point. While her entrance on a motorbike was picturesque, she looked equally graceful in black gear and a ponytail.

5 Worst: Stephanie's Arrest

Brie Bella and Stephanie McMahon had an impressive rivalry in 2014 when the two women crossed paths at 2014 SummerSlam. Building up this bout, Stephanie and Brie had several encounters in the ring, with the former playing the heel.

Just a couple of weeks before SummerSlam, the two opponents had a face-off on RAW. Brie, who entered the ring from the audience, got slapped. As a result, Stephanie was arrested. Given the intensity of the segment, her red dress didn't match the scenario. The internet community also made memes from Stephanie's infamous red dress on the red brand.

4 Best: SummerSlam Attire

While Stephanie was denounced for her dress on RAW, she silenced the critics wearing a beautiful ring gear at SummerSlam to take on Brie Bella. Considering it was her first pay-per-view bout in a decade, she was willing to make a statement, and she certainly did with the SummerSlam dress.

It was a black dress with a slick design, which looked to be inspired by Batman costume. The Billion Dollar Princess won the match, even though she got assistance from Brie's sister, Nikki Bella.

3 Worst: The Shorts

Despite being over forty years old, Steph looks incredible for her age. She works hard to keep a toned physique, alongside her husband, Triple H. The couple doesn't shy away from sharing their workout routines on social media platforms.

Given her corporate villainous character on TV, the fans wouldn't expect her to wear shorts. However, she wore this part of printed shorts on screen, which fans felt were too casual for the event.

2 Best: WrestleMania31

WrestleMania is the biggest event of the year, and some of Stephanie's best looks are from the Showcase of Immortals. Ronda Rousey made her maiden WWE appearance at WrestleMania 31, even though she was still an MMA fighter. Rousey and The Rock produced an unforgettable segment with Stephanie and Triple H, which became the highlight of the event.

Stephanie wore a stunning black dress at WrestleMania 31, and she carried it with ease.

1 Worst: The Blue Outfit At WrestleMania 18

The Grandest Stage of them All might have seen some scintillating attires with bright colors, but a couple of them had backfired by making the list of worst dresses. Stephanie chose to wear such a dress at WrestleMania 18, where she was at the ringside for the match between Triple H and Chris Jericho. Nevertheless, she was there to support Jericho.

Steph wore a blue leather jumper, which didn't go well with her overall. Understandably, it was in fashion in the early 2000s, but she didn't manage to pull it off.

NEXT: 5 Wrestlers That Became Friends Of Shane McMahon (& 5 Who Became Friends Of Stephanie)