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 
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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.
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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|
|2009-08-24||WWE Monday Night Raw||Camo||Shirt|
|2009-08-31||WWE Monday Night Raw||Camo||Shirt|
|2009-09-01 [aired 2009-09-04]||WWE Friday Night SmackDown||Camo||Shirt|
|2009-09-07||WWE Monday Night Raw||Camo||Shirt|
|2009-09-13||WWE Breaking Point (2009)||Camo||Shirt|
|2009-09-14||WWE Monday Night Raw||Camo||Shirt|
|2009-09-25||WWE House Show (León, Guanajuato, Mexico)||Big DX||?|
|2009-09-26||WWE House Show (Guadalajara, Jalisco, Mexico)||Big DX||Shirt|
|2009-09-29 [aired 2009-10-02]||WWE Friday Night SmackDown||Big DX||Shirt|
|2009-10-04||WWE Hell in a Cell (2009)||Camo||Shirt|
|2009-10-05||WWE Monday Night Raw||Camo||Shirt|
|2009-10-19||WWE Monday Night Raw||Camo||Shirt|
|2009-10-25||WWE Bragging Rights (2009)||Camo||Shirt|
|2009-10-26||WWE Monday Night Raw||Camo||Shirt|
|2009-11-04||WWE House Show (Dublin, Ireland)||Camo||Shirt|
|2009-11-05||WWE House Show (Glasgow, Scotland, UK)||Big DX||Shirt|
|2009-11-06||WWE House Show (Newcastle, England, UK)||Big DX||Shirt|
|2009-11-08||WWE House Show (Liverpool, England, UK)||Big DX||Shirt|
|2009-11-09||WWE Monday Night Raw||Camo||Shirt|
|2009-11-10||WWE House Show (Cardiff, Wales)||Green Xs||?|
|2009-11-11||WWE House Show (London, England, UK)||Green Xs||Shirt|
|2009-11-12||WWE House Show (Birmingham, England, UK)||Green Xs||Shirt|
|2009-11-13||WWE House Show (Lyon, France)||Green Xs||Shirt|
|2009-11-14||WWE House Show (Lyon, France)||Green Xs||Shirt|
|2009-11-16||WWE Monday Night Raw||Camo||Shirt|
|2009-11-22||WWE Survivor Series (2009)||Camo v2NEW!||Shirt|
|2009-11-23||WWE Monday Night Raw||Camo v2||Shirt|
|2009-11-30||WWE Monday Night Raw||Camo v2||Shirt|
|2009-12-07||WWE Monday Night Raw||Camo v2||Shirt|
|2009-12-13||WWE TLC: Tables, Ladders & Chairs (2009)||Camo v2||Shirt|
|2009-12-14||WWE Monday Night Raw||Camo||Shirt|
|2009-12-20 [aired 2009-12-25]||WWE Friday Night SmackDown||Camo v2||Shirt|
|2009-12-28||WWE Monday Night Raw||Camo v2||Shirt|
|2009-12-30||WWE House Show (Syracuse, New York, USA)||Camo v2||?|
|2010-01-04||WWE Monday Night Raw||Camo||Shirt|
|2010-01-11||WWE Monday Night Raw||Camo v2||Shirt|
|2010-01-18||WWE Monday Night Raw||Camo v2||Shirt|
|2010-01-25||WWE Monday Night Raw||Camo v2||Shirt|
|2010-01-26 [aired 2010-01-29]||WWE Friday Night SmackDown||Camo v2||Shirt|
|2010-01-31||WWE Royal Rumble (2010)||Wings (Bronze)||None|
|2010-02-01||WWE Monday Night Raw||Camo v2||Shirt|
|2010-02-08||WWE Monday Night Raw||Camo||?|
|2010-03-01||WWE Monday Night Raw||Scales||Shirt|
|2010-03-13||WWE House Show (Fresno, California, USA)||Black Crosses||Shirt|
|2010-03-15||WWE Monday Night Raw||Wings (Bronze)||?|
|2010-03-22||WWE Monday Night Raw||Scales||Shirt|
|2010-03-28||WWE WrestleMania XXVI||Wings (Black)NEW!||Wings (Black) topNEW!|
|2016-04-03||WWE WrestleMania 32||Camo||Shirt|
|2018-11-02||WWE Crown Jewel (2018)||NXTNEW!||NXT topNEW!|