It means "you should walk more like a woman" and it comes from the Tv show Rupaul's Drag Race.
just look at Penny Tration's runaway in the first episode of Drag Race and listen to RuPaul's "You betta Sissy that walk"
by Euroshima March 4, 2014
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Phrase used by Mother RuPaul on the Emmy Award winning "RuPaul's Drag Race" as well as in the song of the same name. Used to describe someone walking confidently on the runway like they own the room.
"If I fly or if I fall, at least I can say, I gave it all. Now Sissy that Walk."
by kaufmasd February 19, 2021
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