Shawn Michaels has always been known as one of wrestling's most flamboyant superstars. As soon as he threw Marty Jannetty through a window and ended their partnership as the Rockers, he adopted the "Heartbreak Kid" persona, fashion became a calling card of his. Known for broken hearts on his tights, wearing chaps paying homage to his Texas roots, and some fancy entrance vests, Michaels always made his attire memorable.

However, Shawn Michaels' gear wasn't always something to be remembered positively. The good outweighed the bad, but there were definitely some questionable choices in attire. With that in mind, we've looked back at Shawn's career to find the very best and very worst that he's worn.

Updated on April 3rd, 2022 by Tevon King: Shawn Michaels is one of the greatest wrestlers of all time. The Heartbreak Kid's wrestling career has been littered with many memorable moments. Whilst, HBK has generally been at the top of his game throughout his career, Michaels has often worn a great outfit alongside his persona. However, there have been some occasions, where Michaels has failed to look the part which is surprising. Generally, Michaels has worn some fantastic outfits on some of the biggest nights in his career. Michaels wears long tights, and he has often had patterns on them. In later years, the two-time WWE Hall of Fame wore tights with the cross on them, to showcase his faith as a Born-Again Christian. Nevertheless, HBK is an all-time great, and it's only right to look further at his five worst and five best attires with a few more additions.

15 * Best: Vengeance 2006

In the summer of 2006, Shawn Michaels and Triple H reunited DX. They went back to their roots, and they sported DX colors. Of course, Michaels and Triple H were mature from the last time they were in DX together back in 1998. Nevertheless, at Vengeance, the deck was stacked against DX as they collided with the Spirit Squad in a two-on-five handicap match.

This was one of Shawn's best attires as he sported his vintage black tights with the green connotations of DX on it. Nevertheless, the bout itself was one-way traffic with DX dismantling the Spirit Squad with ease.

14 * Worst: The Rockers Purple Tights

Shawn Michaels and Marty Jannetty were collectively known as the Rockers. They are arguably one of the greatest tag teams to never win the WWE Tag Team Championship. Nevertheless, whilst the Rockers had some great looks, Michaels' purple tights were awful.

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They were plain, and a pattern on there could have made the outfit look appealing. HBK had long blonde locks and whilst the Rockers were introduced in WWE in 1988, fortunately, their outfits improved drastically.

13 * Best: In Your House: The Lumberjacks, 1995

At In Your House: The Lumberjacks, Shawn Michaels challenged Jeff Jarrett for the Intercontinental Championship. Despite Double J competing in his hometown of Nashville, Tennessee, a difficult title defense was in store for him as Michaels was motivated to win the Intercontinental Championship once again.

HBK has had many superb outfits over the years, and wearing white has always suited Michaels. The pattern on his white tights was with golden love hearts. It proved to be a successful night for Michaels as he executed a Sweet Chin Music on Jarrett to become a three-time Intercontinental Champion.

12 * Worst: TLC 2009

Shawn Michaels was in the final stretch of his wrestling career before he retired at WrestleMania 26. However, something was missing from Shawn Michaels and Triple H's resume and that was a Tag Team Championship victory together. DX was looking to put that right, and they challenged Jeri-Show for the Unified WWE Tag Team Championship at TLC 2009.

Their TLC match was exceptional, and that was the main positive about the match. Unfortunately, HBK's attire was poor by his standards. A dark brown color mixed with green did not mesh well. Ultimately, DX went home with the Unified WWE Tag Team Championship.

11 * Best: Royal Rumble 1998

The 1998 Royal Rumble proved to be a significant night in the Attitude Era. Shawn Michaels defended the WWE Championship against The Undertaker in a casket match. The casket match is Undertaker's specialty, but HBK was determined to cling to his WWE Championship.

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Red and white go well together, and this was unquestionably one of Michaels' best attires. Although he came down the aisle with DX music, Michaels was still the Heartbreak Kid. However, the Phenom launched Michaels over the casket, and HBK's back caught the edge of the casket. He herniated some discs in his back, and he was ruled out of action for four years after WrestleMania 14. Nevertheless, HBK retained the WWE Title, all thanks to interference from Kane.

10 Worst: Camo Chaps

We fully understand why this gear became a thing. As the personal lives of wrestlers became more public, we learned that Shawn Michaels is an avid outdoorsman. He enjoys hunting and even has a television series based around it. On his casual days, he's often seen wearing camouflage.

That translated over into some of his ring gear. This ensemble was his chosen apparel for a short appearance at WrestleMania 32. As much as it may fit the man behind the wrestler, it's not what we want from our "Heartbreak Kid." This attire ultimately felt like it wasn't enough of the Shawn Michaels we have come to love.

9 Best: Royal Rumble 1997

If Shawn Michaels was going to pay homage to his roots, this was the way to do it. After winning the Royal Rumble match in back-to-back years, Shawn entered the 1997 show as a challenger for the WWE Title. He looked to regain it from Sycho Sid, who had taken it from him two months prior.

Shawn had the home-field advantage as the event took place in the cavernous Alamodome in San Antonio, Texas. As a fitting gesture, Shawn sported red, white, and blue tights with the Texas flag in each of the hearts. He also had the shape of Texas on his wristbands. It sounds weird on paper, but it all came together well on a night when Shawn won his second WWE Championship.

8 Worst: Survivor Series 1992

It's the oldest attire on this list. Shawn wore it at more shows than just Survivor Series 1992, but it's his most notable match with it. On that night, he challenged Bret Hart for the WWE Title in his first pay-per-view main event. Honestly, this gear isn't flat-out bad or anything like that.

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It's just that this gear is missing something to make it scream "Heartbreak Kid." When they figured out that the designs on his tights should be in the shape of hearts, they struck gold. Here, it looks like his tights have clouds on them. That's just not all that interesting or fashionable.

7 Best: WrestleMania 25

In a career filled with phenomenal matches, this night might have been Shawn's finest. At WrestleMania 25, he and The Undertaker wrestled a 25-minute classic that is considered one of the best matches of all time. It may sound odd, but the ring gear Shawn sported that night actually played a role in the story.

During their entrances, Undertaker rose from beneath the stage clad in all black. Meanwhile, Shawn descended from the heavens in all white. Heaven against hell. The tights were white and the chaps having the right tint of gold to them really added a lot to pull it all together.

6 Worst: Crown Jewel

When Shawn Michaels retired after a loss to The Undertaker in 2010, many felt it was the perfect sendoff. Nobody had ever gone out on a higher note. Though fans clamored for one more match, Shawn never did it, and it kept that final performance special. However, Shawn finally caved for a show in Saudi Arabia last year.

This was a strange look for Shawn Michaels. The obvious difference was that he was now bald, which is a huge change from the rest of his career. But the attire was also incredibly generic. Just black and white chaps over black and white tights? You can do better than that Shawn.

5 Best: Blue And Black Tights

We may not have an exact date for when Shawn Michaels wore these tights, but that's okay. They had to be included because they look great. Blue wasn't a color Shawn wore often. He would throw it in with red or black here and there, but it was seldom the dominant color.

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That changed here. These tights were mostly a light shade of blue with some black thrown in. The hearts were each that same blue and had white trim around each of them. Shawn looked great, and it was just different enough to feel somewhat unique.

4 Worst: Raw 11/25/02

When Shawn Michaels first returned from his four-year absence after a back injury, he had some rough times with attires. Right after shocking the world and winning the World Heavyweight Championship, Shawn defended it on Raw against Rob Van Dam. He did so while wearing attire that still doesn't make sense to this day.

As noted, Shawn was always known for being extravagant and flamboyant. This gear was just black tights with the letters "HBK" written down the side. Even the white and red colors included are bland. This looked like something designed for a video game by someone who didn't have enough time to finish.

3 Best: Mind Games

This is a case where the red, black, and white color scheme worked perfectly for Shawn. When he donned black, it was rare enough that it felt special. He busted it out for this 1996 battle with Mankind that proved to be one of the finest matches in any promotion during that decade.

This attire was mostly a simple concept. Red, white, and black is a color scheme that is used by many wrestlers throughout history. There was just something about the way it all came together that made this such a great attire.

2 Worst: Survivor Series 2002

Honestly, if you know anything about Shawn Michaels then you know this was an obvious choice for his worst attire. Survivor Series 2002 proved to be a milestone night for HBK. In just his second pay-per-view since missing four years with a back injury, he won the World Heavyweight Championship by outlasting five other stars in the first Elimination Chamber.

That makes it extra unfortunate that he didn't look anything like a champion on this night. Apparently, the person who made Shawn's gear wasn't able to finish them in time. That meant only a few hearts were stitched into the design. But the worst part was the color choice. The odd tint of brown reminded people of some gross things and wasn't fitting of a guy like Michaels.

1 Best: WrestleMania 12

It's fitting that the biggest night of Shawn Michaels' career was also when he wore his best attire. In the main event of WrestleMania, he squared off against rival Bret Hart in the first-ever Ironman Match for the WWE Championship. Shawn wound up winning that title for the first time in his career.

While pulling off this incredible accomplishment, Michaels wore white tights with gold hearts all over them. The black trim surrounding each of the hearts looked awesome and his trademark O'Neal boots never looked better. It was the perfect attire to wear for a night that would end with a championship victory.