Headphones

Slim glasses or IEMs.

For me, I swapped to softer ear pads which can easily contour around the rims of my glasses. Velour to cooling gel pad for X2HR. I also reduced the clamp by stretching it over the box that it came from for a week.

You need something with less clamp. I can use my he400i with glasses no prob

welcome to iems my fellow eyeglasses user!

I daily drive a Sennheiser HD560s with the velour pads and I can wear them all day no problem with my glasses on

Frames of the right width (i.e. temples parallel with side of head when worn) with thin enough temples & temple tips. Slimmer replacement temple tips. MacGyvering temple tips yourself...

I went through the same thing this summer after getting new glasses. The previous ones that pretty much the ideal frames when it came to comfort, so of course I wanted a similarly slim design. That plus my preferred rectangular-ish lens shape turned out trickier than I had anticipated. Had to visit many an optician's before finding that same type of frame design I wanted. It seemed like noticably larger, bulkier frames with more rounded lenses was all the rage nowadays. Goddamn fashion trends... :D

So, got the new glasses, they're good, and I thought the new frames were more or less similar in temple slimness compared to the old ones, they at least seemed like it, but nope! Temple tips dug into the side of my head within minutes of wearing any on-ear or over-ear headphones, even those I could wear with no issues whatsoever for hours on end wearing my previous glasses.
Queue almost half-a-dozen trips back to the optician's for adjustments (thankfully only a short bike ride away), them getting silicone replacement tips from another store location (in the end we didn't even bother trying those on, as they turned out to be as thick as the original tips), and then finally me suggesting giving it a try just taking off the temple tips entirely to test how they'd be without them. Seemed initially good, comfy with headphones, but eventually the too thin metal tips started digging in, even without wearing headphones. I ended up DIYing new temple tips from pieces of the outer jacket of some electrical wiring (original temple on the left), might have even been some ear/headphone cable. Great success! Looks the part and comfort's back to as good as with previous glasses.