Starting with… the solo debut (after the breakup of the Rockers) at Royal Rumble ’92.
Arguably one of the best americans wrestlers of both the New Generation era and the Ruthless Aggression era, Shawn Michaels was also one of the flashiest ones. From tights with big hearts to chaps with chains, the Showstopper stopped at nothing to make an impression on the audience before even getting in the ring.
Main outfit 
The (Midnight) Rockers often had some kind of zebra pattern on their tights, and Shawn kept that tradition going with his new tights. They were almost always seen with black knee pads, except on very rare occasions where white ones made more sense esthetically, a trend that would continue until WrestleMania XI; we could also see matching zebra or red zebra pads from time to time in late 92-early 93.
1994 is the first of three consecutive years where changes would debut at WrestleMania, this year having the biggest one of them with the introduction of the broken heart tights!
Starting with this year’s WrestleMania, outfits now have matching gloves and knee pads, although their use is going to be pretty chaotic for a while. (They also had a generic cut and would be switched constantly, so the right glove from one day would be the left one the next day, and vice-versa. Same with the knee pads.)
Another change would come at the end of the year, with the zebra pattern now having larger stripes.
Finally, starting with this year’s WrestleMania, gloves and knee pads will now have the same broken heart symbol as the tights, instead of its pattern only.
For his comeback, Shawn wanted to change his image, and tried something different for a while.
This wouldn’t last more than a couple of matches, though, and he quickly went back to his old style, without the matching gloves. Also, starting at the end of the year, the new tights appear to not have separate trunks anymore.
Big change at WrestleMania! Gone are the tights! From this point on, Shawn will wear larger pants with integrated chaps, with the only throwbacks of the 90s HBK being little broken hearts on the belt area. This wardrobe update would also have an incidence on the entrance outfits.
Switching from just a top to a full outfit with chaps might be the boldest choice Shawn ever made. And yet, he made it work!
And now, with hats!
Almost 2 years after coming back, Shawn finally had some new chaps made.
With the tights being replaced by the large pants, the entrance outfits will now be just a matching top, although he started to wear a simple shirt instead more and more.
|Date (YYYY-MM-DD)||Event||Main outfit||Entrance|
|2008-05-24||WWE House Show (Mexico City, Mexico)||Red Studded||Shirt|
|2008-05-26||WWE Monday Night Raw||Thorns||Shirt|
|2008-06-01||WWE One Night Stand (2008)||Black Crosses||Shirt|
|2008-06-20||WWE House Show (Las Cruces, New Mexico, USA)||Red Crosses||?|
|2008-07-02||WWE House Show (Santiago de Chile, Chile)||Red Studded||Shirt|
|2008-07-03||WWE House Show (Lima, Peru)||Black Crosses||?|
|2008-07-04||WWE House Show (Panama City, Panama)||Red Studded||?|
|2008-07-11||WWE House Show (Lexington, Kentucky, USA)||Shields||Shirt|
|2008-07-13||WWE House Show (Roanoke, Virginia, USA)||Thorns||?|
|2008-07-20||WWE The Great American Bash (2008)||MuddyNEW!||Shirt|
|2008-09-07||WWE Unforgiven (2008)||Other [jean & shirt]||None|
|2008-09-22||WWE Monday Night Raw||Thorns||Shirt|
|2008-09-24||WWE House Show (Bilbao, Spain)||Thorns||?|
|2008-09-25||WWE House Show (Madrid, Spain)||Thorns||?|
|2008-09-26||WWE House Show (Barcelona, Spain)||Thorns||?|
|2008-09-27||WWE House Show (Paris, France)||Thorns||Shirt|
|2008-09-29||WWE Monday Night Raw||Black Crosses||Shirt|
|2008-10-05||WWE No Mercy (2008)||Scales||Shirt|
|2008-10-06||WWE Monday Night Raw||Scales||?|
|2008-10-13||WWE Monday Night Raw||Muddy||Shirt|
|2008-10-16||WWE House Show (Arecibo, Puerto Rico)||Black Crosses||Shirt|
|2008-10-18||WWE House Show (San Juan, Puerto Rico, USA)||Scales||?|
|2008-10-27||WWE Monday Night Raw||Scales||None|
|2008-11-03||WWE Monday Night Raw||Big DX||Shirt|
|2008-11-10||WWE Monday Night Raw||Thorns||Shirt|
|2008-11-12||WWE House Show (Newcastle, England, UK)||Thorns||Shirt|
|2008-11-13||WWE House Show (Belfast, Northern Ireland, UK)||Thorns||Shirt|
|2008-11-17||WWE Monday Night Raw||Black Crosses||Shirt|
|2008-11-23||WWE Survivor Series (2008)||Muddy||Shirt|
|2008-11-24||WWE Monday Night Raw||Muddy||Shirt|
|2008-12-22||WWE Monday Night Raw||Thorns||Shirt|
|2008-12-27||WWE House Show (Trenton, New Jersey, USA)||Red Studded||?|
|2008-12-28||WWE House Show (New York City, New York, USA)||Black Crosses||Shirt|
|2008-12-29||WWE Monday Night Raw||Black Crosses||Shirt|
|2009-01-02||WWE House Show (Sunrise, Florida, USA)||Black Diamonds||Shirt|
|2009-01-05||WWE Monday Night Raw||Thorns||Shirt|
|2009-01-12||WWE Monday Night Raw||Thorns||Shirt|
|2009-01-26||WWE Monday Night Raw||Thorns||Shirt|
|2009-01-31||WWE House Show (Hammond, Indiana, USA)||Red Studded||?|
|2009-02-09||WWE Monday Night Raw||Grey||Shirt|
|2009-02-13||WWE House Show (Los Angeles, California, USA)||Black Diamonds||Shirt|
|2009-02-15||WWE No Way Out (2009)||Black Crosses||Shirt|
|2009-02-23||WWE Monday Night Raw||Thorns||Shirt|
|2009-02-27||WWE House Show (Long Island, New York, USA)||Black Diamonds||?|
|2009-03-02||WWE Monday Night Raw||Grey||Shirt|
|2009-03-16||WWE Monday Night Raw||Black Crosses||Shirt|
|2009-03-17 [aired 2009-03-20]||WWE Friday Night SmackDown||Grey||Shirt|
|2009-03-29||WWE House Show (Hidalgo, Texas, USA)||Thorns||Shirt|
|2009-04-05||WWE WrestleMania XXV||Wings (Bronze)NEW!||White Hat and CoatNEW!
Wings (Bronze) topNEW!
|2009-08-23||WWE SummerSlam (2009)||CamoNEW!||Shirt|