Heelys 

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.

Heelys by Dalya March 25, 2003

Heelys 

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!

Heelys by IDKWHOTHISIS February 2, 2008

heelys 

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

heelys by Petey Paublo November 1, 2007

Heelys 

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"

Heelys by Anon227 September 13, 2011

Heelys 

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.

Heelys by The Big H May 5, 2007

Heelys Jew 

The epitome of the perfect woman, she glides the halls like a leprechaun on acid. Don't come for her, or she will talk about her mom's brain surgery.

Did you see heelys jew yesterday? She was wearing her camo heelys.

Heelys Jew by hochaum December 10, 2016

Head Over Heels 

When you're incredibly in love with someone that you see them and your heart goes one hundred miles per hour.

Angel is head over heels for ashley

Head Over Heels by Sharkisha Cole December 1, 2018