Any over-the-ear headphone recommendation for glass wearers?

So I'm a bit of a self-professed audiophile -- and I also wear glasses from time to time.

Although I generally prefer the acoustic detail I get from in-ear monitors like the Etymotic ER-4SR, I really like a few open-back over-the-ear headphones.

If you're okay with wired headphones, my favorite midrange over-the-ear headphone is the Sennheiser HD650 (also sold as the HD6XX on Drop). They're fairly affordable, and they have excellent sound stage and imaging.

The HD650/6XX have the typical "Sennheiser sound," so they're a bit on the "warmer" side when it comes to tonal balance, but this makes them sound very pleasing overall -- especially if you like soft vocals and rich bass. Another great option is the HD58X, which is a bit more detailed but with less bass -- and it costs a bit less too.

All of these are really comfortable -- even with glasses -- thanks to their plush ear pads and great shape.

I have a large head and find most over the ear headphones uncomfortable. I took a random shot on a pair of Beats Studio3 Wireless and, while the sound could be a bit better, they are one of the most comfortable headphones I've ever used. They work well with my earrings, glasses, and even when wearing my cap.

My only annoyances with them are that they’re a bit expensive, they still charge with MicroUSB, and the sound could be better out of the box.

As a glass wearing software developer and gamer who wears headphones for at least 10h most days I can relate. For me the AKG wire head strap is the best. Provides just enough tension to keep them close without feeling any pressure. A bit bulky for wearing out and about but if you spend most of your time sitting at a desk I don't think they can be beat for comfort and sound quality. They are also extremely lightweight so you quickly forget you are even wearing headphones.

As starting point I would recommend something like the AKG K240 MKII

As for wireless vs wired I prefer wired just for my setup. If you want to go all out for comfort I'd recommend looking for a paracable cord as they are lighter and more flexible. As long as you don't walk away from your desk with them on you will hardly notice the cable compared so some heavier coiled cables. Wireless headphones are generally a little heavier so I tend to stay away from them.

I can't claim to be an audiophile but I do demand good sound! I personally love the wired Audio-Technica ATH-M40x. They're my go-to for music and other media purely for the sound and comfort. They have super plush cushions that allow for long periods of wearing. They do form around the frames of my glasses nicely too. I do prefer the stronger clamping pressure of these (nothing too crazy) but I could see that possibly being a problem for others with frames.

I also have the wired SteelSeries Arctis 1 that I use for work (need the mic of course). They're extremely comfortable and the speaker/mic quality is amazing for the price point. The cushions are some sort of fabric that does get a touch warm though. The cord could be bit longer too but that's probably something I can replace. I also might upgrade these to the wireless 2.4GHz wireless (non-Bluetooth).

I'm very happy with both of these!

Having a pair of cheap plastic glasses frames that actually bow out from my temples, I can confirm personal comfort with a few different headphones from Sennheiser. I primarily use a Game One when at my computer and a HD595 when on the couch; both have velour (comfort?) pads and both are comfortable for hours (and hours) at a time. I occasionally use a DJ8 with pleather (isolation?) pads and despite their high clamping force, the only discomfort I experience is where they rest at the crown of my head from how heavy they are. The ONLY complaint I have with over-ears is the matted hair that is squished around the ears and ends in exaggerated curls around the border my ear, haha.

When I'm not in the mood for headphones, a comfortable alternative could be something like the Bose IE series. They're buds that rest in the outer ear and have a tip that funnels decent audio quality in while remaining relatively open to the environment. Good long-term comfort and sound that leaves your hair and glasses alone while allowing you to remain aware of your surroundings.