The evolution of Henry the Octopus (1992 - Present).
- 1992 - 1996: The original Henry costume represents a major departure from later costumes. He has small eyes, eyebrows, and a very pale purple color. Also, rather than a bowtie, he sports what appears to be a belt on his neck.
- 1996 - 1997: Henry's design is given a slight overhaul, he now has bigger, more oval-shaped eyes. His skin is in a mauve colour. His belt is also redesigned slightly.
- 1997 - 1998: Henry's design is given another overhaul. Instead of a belt, Henry now has a bowtie. His bowtie goes down at the bow. Now his tentacles are rounder and all of his shoes shine. His skin is now a blue-violet color.
Appears in: The Wiggles Movie, Wiggly, Wiggly Christmas, Wiggle Time (re-recording), Yummy Yummy (re-recording), The Wiggles (TV Series 1), The Wiggles: Live at Disneyland, Toot Toot! (cameo) and The Wiggly Big Show (cameo).
- 1998 - 2001: Similar to the previous costume, but now his blue-violet color is darker and his head is rounder and taller. The patterns on his clothing are also changed slightly. His bowtie is now more straight.
Appears in: Toot Toot!, The Wiggles (TV Series 2), The Dorothy the Dinosaur and Friends Video, Dorothy the Dinosaur Goes to Hospital, The Wiggly Big Show, Wiggly, Wiggly Christmas (1999 cameo) in "Wiggly Christmas Medley"), Captain Feathersword, the Friendly Pirate, It's a Wiggly, Wiggly World, Wiggly TV and the Hoop-Dee-Doo: It's a Wiggly Party cover.
- 2000 - 2007: Henry now has a more cartoony design. He looks a bit chubbier than previous costumes, and his shoes are rounder and his tentacles are curved. His head is skinnier and his hat is now straight on the top of his head instead of crooked on the side. The patterns on his clothing and hat are given a complete overhaul.
Appears in: Yule Be Wiggling, Hoop-Dee-Doo: It's a Wiggly Party, Wiggly Safari, Whoo Hoo! Wiggly Gremlins!, Wiggle Bay, Space Dancing world premiere, Top of the Tots, Cold Spaghetti Western, Santa's Rockin'!, Live Hot Potatoes, Sailing Around the World, Here Comes the Big Red Car, It's Time To Wake Up Jeff!, Splish Splash Big Red Boat, Wiggledancing - Live In The USA, Racing to the Rainbow and Wiggledancing! Live in Concert.
- 2007 - 2010: This costume is like the last one except that he now has gloves and his head is bigger.
- 2009 - 2015: The costume has a skinnier head and Henry's eyes are smaller. Henry's gloves are now back to shoes. Henry looks like his eyes are both looking in different directions. And his head looks like fabric.
- 2015- present: Henry goes through a slight overhaul. He doesn't have much fabric as the last one did but he looks slightly cuter.