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Bret wore shades because of his camera-shyness that he slowly overcame. Bret slicked his hair because the wet look went with the body oil and fake sweat literally all wrestlers did at that time because it brings out the muscles and looks great on camera. The tassles on the leather jacket hearken back to his country western roots, the four hearts seen on his tights represent his four children and he places dots above his autograph signature for the same reason. The bright pink motiff was not his idea; it was instead the strong suggestion of the seamstress who made their tights whom neither he nor Neidhart ever met. They were getting pressure from the office to switch up their gear a little for their tag team and every time Bret called her, all she kept saying that she had was this hot pink. Bret wasn't feeling it and when he brought it to Neidhart, he was absolutely against it. Literally a week goes by and he calls her back and says the same thing that all she had was this hot pink. Neidhart, to his credit, did a 180 and figured pink wouldn't be so bad. When the arena lights hit them, they were so bright it burnt the sensors out of the cameras. Bret's tights incorporated more black than pink the more of a heel he played.
Friendly reminder that Stephanie McMahon's favourite wrestler is Bret Hart.