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I walk to be able to walk and wear 5inch stilettos and not buy too many pairs on the way how do you recommend i and other members get there?

Like everyone says, start of with lower block heels. It is unreasonable to expect to be able to step into 5" stilettos and enjoy walkiung. Fumbling around in ill fitting heels that are too tall is a confidence killer. Being confident is just as important as being skilled.

Same here. I wear knee boots and invariably have to remove them.

Yes. Make sure they fit well and are well made.

I have too take my heels off to go through security at airports. And I fly in knee highs on the outside.

But make sure whatever you buy fit WITHOUT pain. Life is too short for shoes that hurt.

If you’ve never work heels I’d try chunky 3 to 3.5” to start, than then maybe four inch (10cm) stilettos. Take your time. There’s no rush

Should I go for chunky but higher or lower stilettos how would you suggest i "graduate"?

If you’ve never worn heels before you’re going to need to buy at least one other pair and probably two - a lower heights to get you familiar with the feel of wearing heels. And even then it will take time, patience and perseverance. Five inch heels - or 12cm - is a challenging height even for experienced high heel wearers with years of experience. There is no easy way

So I decided to wear heels to Jury Duty. The pants mostly covered things but security noticed that I had heels on and asked me to send them through the scanner. Nothing major to say, as I wore mary jane flats the next time.