Might mean (unverified): Shoes with wheels in heels.
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We found one dictionary that defines the word heelie:

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  1. heelie: Wiktionary

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Definitions from Wiktionary (heelie)

▸ noun:  (skateboarding, slang) heelflip

Similar:
halfie, hippy jump, headie, helipad, heeling, hip whip, heep, heliskiing, Huey, heliskier, more...

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Similar:
halfie, hippy jump, headie, helipad, heeling, hip whip, heep, heliskiing, Huey, heliskier, more...



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