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Depends on the height of the heel and  the make of the shoe. For example shoes with a high heel but have a platform base (at the front) will support you better than a shoe that doesn't. Also more expensive shoes/boots (like Karen Millen, Kurt Geiger etc) are a lot more comfortable to wear because of the way they are made.

The best way to wear heels with minimum damage is to wear a wedge heel, you can walk for hours and still get height (not that you blimmin need it Sazza you tall person )

Karma_
I rarely wear heels now... & nothing like the ones I used to wear.

The secret is to wear them pretty much all the time.  Even in the house.   You adjust to wearing them.  Though be warned... the reason I can't wear really high heels, and tend to live in boots, trainers & flats is cos I have a bunion caused by wearing very very high heels.
Dirtyprettygirlthing
Reference:
I thought that was maybe it, just being used to them
and being prepared to take twice as long to get anywhere on foot... tottering along.. rather than striding briskley!   Oh... & not actually puttng your heel down, tottering on tippy toe,  when you are on grass or mud... or there are leaves on the ground (or you end up collecting them)... 

there is a lot to be said for trainers!
Dirtyprettygirlthing
Reference:
on this subject i have broken heels , i stand for 8hrs 6 days a week i only wear flats and no way in this earth could i wear heels, i was told to rub arnica cream into my joints but no joy ............ any hints on pain relief guys

If you are wearing completely flat shoes then your calves and shins will ache as your foot is completely flat on the floor (I used to get this when I used to try walking for any length of time in flats).

Try getting a leather shoe with a slight wedge heel that will support your arches and give you a better posture, maybe a 1 1/2 - 2inch heel, not too high but will be better than flats. Clarks do some ok shoes (they're not all for 60+ arthritic people!)
Karma_
I can not for the life of me wear heals and god iv tried!! Every time i go out i start the night in a sexy pair of heals two hours later i heading home for the flats. Luckily i live 2 mins from town centre but if i ever head further a field i carry a spare pair of flats in my handbag and i make sure i wont mind throwing the heals i start off wearing away
Sexy_Kelly

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