Would these fit Oakley Straight Jacket frames?

I don't know what those frames even look like, tho I think you refer to the ends of the ear pieces. If the ENTIRE ear piece is a thin, straight piece, the Croakie may be too loose. If it widens at the end for comfort it probably will be fine. On my frames, it is NOT easy to slide the croakie over the wide end, but once on, they hold as you want them to. Without the croakie holding the glassed where they belong, I literally could NOT work.

Heavy medical glasses will it hold them up

I wear very large Aviator style glasses, and the Croakies hold them with no problem.

What makes these "XL"? Are they longer or is it that the opening is larger to accommodate a wider/thicker eyeglass temple

The strap is the same length as the standard but it is 1/4" wider, 1" rather 3/4". But the main difference and reason for getting the XL is that it will accept a larger frame. I got them because my sunglasses would not go into the standard.

Is the XL opening available in the 3/4 inch width or is it larger?

The XL opening is not available on the 3/4" strap. I bought these because the 3/4" would not allow me insert the stems of my sunglasses.

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