I only want to use this retainer for working out at the gym, not for regular use. Are these retainer ends able to withstand frequent removals?

they are meant to go on, and stay on. frequently removing would make the rubber end sockets wear out quickly. they might even say somewhere that they're not really meant to be taken on/off frequently as well.

How do you decide or measure to get the right size?

I averaged between the largest and the smallest measure and tied a string on my glasses and I could visualize the size that would be good for my use.

Are these a stiff wire type of holder? If they are loose on the back of my head, will the excess(curved wire) just sorta stick straight out the back ?

They are made with stainless steel wire. They are adjustable. So depending on the length you buy when adjusted all the way tight it will fit snug at the back of the head. If you want to remove your sunglasses you just the wire adjusters to give slack and you can lower or remove your sunglasses. I buy the 14 inch. They last forever. I use mine every day and wore them fishing every time in salt air. Never had one go bad yet after many years of use.

Can it be used with Okaly half jacket

Yes, easily. I have them on my half and flak jackets. As well as a pair of Costa Del Mar which have much larger ear peices. The rubber stretches. Pro tip: use hand sanitizer when applying and they will slide right on and stay there once the sanitizer evaporates.

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