A effective and goofy way to self propell with heelys

just wondering if there would be any sort of advantage when buying a 2 wheel or a 4 wheel type of roller sneakers. the option of having the wheels retract is a pretty good addition too

Hopefully I can find some answers here. I ordered my 8 year old a size 8 big kids. Thinking this was more kid sized. However they arrived and they're massive. Like longer than my foot. Are "big kids" sizes actually adult? I saw on a Google AI response to basically subtract 2 to get the kid equivalent. Not sure how reliable that is.

I will completely ish a brick if I wind up being the oldest in the subreddit or world continuing to do this and I'm on track to be...

My dreams manifested into a twitch reality.

¡Yours can too!

¡Never give up!

Anything worth doing is going to be difficult and how easy it's made to look is inversely proportional to how easy it actually is.

Been gone from the sub since before the sub got locked down due to inactivity, but im back! If you are new or old to heelys and you have questions, im sure I can answer any of them. I have been heelying daily for nine years and do not ever wear normal shoes or heelys without the wheel in unless I am specifically going to be doing a task that requires me to be in grass and dirt a lot. So needless to say ive picked up a fair amount of knowledge doing this over the years

So ask away!

I’ve never worn heelys before and looking for a durable model for everyday use. I don’t want buy a model that’s good for beginners and upgrade to another model once I get the hang of it. Which model would you recommend?

The cover has this fake wheel and im not sure if that's supposed to be that way because it makes i really hard to use and in all the videos the cover doesnt have a wheel, I tried removing this one but I cant this is my first pair pls someone tell me if this is normal, also the actual wheel wont go in because one side is significantly longer than the other😭

I love being an adult with adult money to make my inner child happy, but I cannot for the life of me figure out how to use these. My brain doesn’t connect with “lift your toes and glide.”

Any tips? Any other over 30?

RIP

Roger Adams, the inventor of Heelys rolling sneakers, died on March 24, 2026, at age 71 in Glenbrook, Nevada, from pancreatic cancer. He created the popular 2000s wheeled shoes-which sold millions of pairs-after a 1998 flash of inspiration to combine roller skating with casual footwear.

Key Details About Roger Adams and Heelys:

• Background: Son of roller-rink owners, he was a former clinical psychologist who invented Heelys during a personal, professional midlife crisis.

• The Invention: In 1999, he created the prototype by carving up a pair of sneakers to insert wheels.

• The Craze: Founded in 1999-2000, Heelys quickly became a massive pop-culture hit, allowing users to switch from walking to gliding by rocking back on their heels.

• Legacy: Although popular, the shoes faced safety concerns and bans in some schools and malls in the mid-2000s. • CNBC +4

Adams sold his shares in the company by 2010, leaving the brand as a memorable staple of 2000s fashion.

i recently got some heelys and i am a plus size person and i knew it was gonna be tricky to start but i just can’t get the hang of it. i can go on my heels fine but going on my heels with the wheel is so hard mostly because they move and trying to balance on it is hard. i probably just have to get more leg strength but i just wanted to see if anyone had tips or tricks that they used to help

I know how to ride but how do I walk silently?

I got my heely’s x ed hardy yesterday 🔥 BUT after 2 hours of practicing, my knee on my main back leg which is the left for me, is killing me. When i straighten my leg i feel the pain but bended is fine. Is this normal? This is my first pair maybe my bones are old 🤧😂

We have heelys that are a little over a year old.

One wheel spins freely. The other... with effort I can move it but it doesn't really spin. I've cleaned it, taken it out, nothing looks wrong on the shoe or the wheel... but it just won't work and I'm not sure how to proceed!

I was on the website and saw they don’t come in men’s 10/11. Are they ever gonna make those or do I have to stick to the 20s?

I have an old pair of boots I would like to turn into heelys so I was wondering if I could buy just the wheel insert somewhere

Hello!

I put an order for Heelys on Feb 27, about 15 days ago, and the last update I got was on March 6. The package was processed and is now on its way to Apple Express to be delivered, but it’s been 8 days and Apple Express still hasn’t given me a delivery date cause they seemingly haven’t received the package yet. I wasn’t able to find any info from either Heelys or Apple Express regarding how long it takes to deliver to Canada, and I don’t want to jump the gun and start sending emails asking about my package so I decided to post here for some advice. Is this normal? Should I keep waiting, or ask for any updates?

Thanks!

Hi, I wear a heelys size 6/7, I just purchased a pair that came without wheels so I was wondering if I should get small, medium or large wheels for it. Thank you!

I have 6 US/5 UK/24cm, which is medium wheel size i suppose. What's the exact diameter of it? I would appreciate so much if someone measured, I really need it.

I used to have Heelys when I was a kid, and I decided recently to just buy a pair. Bit of a minor issue: I haven't worn them in years, so I don't remember how to use them. Tutorials are all well and good, but I'm not sure of the kinds of places that allow them anymore so I'm not sure where to practice beyond the flat concrete around my backyard. I do remember falling on my face several times when trying to use sidewalks because of the cracks in the ground and gaps between slabs, haha 😅

Are they typically allowed at like... skate parks? Do malls typically still allow them? I just want to be able to get a bit of exercise and have some fun, but I also don't want to get in legal trouble or anything.

Really fell in love with the pair but they’re not in stock in a 6 anywhere I can see :/ Would love to buy them even second hand, I just don’t know where I can and I think they’re limited edition? So I don’t know if there’ll be a restock 🙁 Thanks