On powerisers, I just sit on the ground and strap them on. You can get up off the ground without help on these (if you're daring) by spreading your legs like you're trying to do a split; then jumping - hard to explain; I'll try to find a photo or video clip.
On drywall type stilts, I generally lean against a wall or such and strap one leg in; then stand on that stilt and strap the other in. A safer way of getting in them is to set on a tall tale or counter (or truck bed - anything high enough to be in a normal setting posistion with once you're in stilts.)
I'll find some photos of me in various stilts - I have one in the gallery here of me jumping on my powerisers - pretty grainy as it was in motion when captured. I'll post some more here in a bit.
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“Listen to the mustn'ts, child. Listen to the don'ts. Listen to the shouldn'ts, the impossibles, the won'ts. Listen to the never haves, then listen close to me... Anything can happen, child. Anything can be.” - Shel Silverstein
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