A shoe with a wheel on it. Makes kids look/act like douches.

The only human being that should be allowed to wear heelys is Toby Turner AKA Tobuscus.
Tobuscus wearing heelys, circling random women.
Tobuscus: "HOTHOTHOTHOTHOTHOTHOTHOT"
by Anon227 September 13, 2011

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Top Definition
Sport shoes that have wheels housed in the heel that allow you to walk, run, and roll at any given moment.
I enjoy riding Heelys.
by Dalya March 25, 2003

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Heelys is an awesome shoe. Too many people stereo-type Heelys. They think they are just stupid little toys little kids use to roll around and crash into people. Well... they are DEAD WRONG!!! Heelys is capable of much more! Look up Team Heelys on YouTube to see for yourself. And YES, HEELYS IS A SPORT! If there is a team for it, its a sport like Disc Golf, Chess, and Mathletics. Heelys are able to grind and even drop-in on vert! Most kids don't know about this because they don't take Heeling (not Heelying or Heelieng) seriously and they only get the trainers. If you want to be able to grind and skate vert, look for the Torch model or Evolution Model. HEELYS ARE AWESOME!
Heeler : Dude! I just did an awesome frontside on the HP (halfpipe)
Non-Heeler : In Heelys? Yeah right, Heelys can't do anything cool!
Heeler : ... Yes ... they ... can!
*does an awesome frontside tru*
Non-Heeler : WHOA! THAT WAS SICK!
*buys Heelys*
Heeler : Smart choice!
by IDKWHOTHISIS February 02, 2008

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These are high heel protectors called 'heelies' not the skate shoes. Also a registered trademark. They are available online in Clear and Black. A plastic tube that is placed over the heel to protect scratches and damage to the heel covering. There has been a lot of confusion over the spelling of this product and the skate shoe.
heelies {heelie's] heelys heely's
by ellcee November 04, 2013

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term used to define anything that would be considered like a trendy, "kid" thing. Coined from the heelys shoe, which for a time was the thing every kid wanted, but really it just made them look like assholes.

Doesn't exactly have to be a "kid" thing either, as the trendy things that teenagers do also apply.
Person A:
"Hey, what did you do to your hair?"

Person B:
"Instead of a weave I had my mom place yarn instead. Isn't it cool?"

Person A:
"That is some Heely-kid shit. Fuck you."
by imfromthesuburbs May 24, 2011

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Pathetic attempt at an extreme sport, only little kids buy them to look cool to their friends, and for kids who gave up every extreme sport they tried.
If your seen in a skatepark with heelys chances are you'll be beaten the shit out of
by Petey Paublo October 16, 2007

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A shoe which I would not be caught dead wearing.
Parents who buy heelys for their kids should be lined up against a wall and shot dead.

Parents who wear heelys themselves should be drawn and quartered.
by The Big H April 15, 2007

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