99 Neo

You've got a large budget. If you're the kind of person who tries to keep the experiences fresh (like I am), maybe consider two different pairs. One for inside use (as people mentioned, Ananda Stealth or Ananda Nano seem to be insanely good for the price planars, but are likely to require EQ, may require a headband replacement, and don't really feel that premium), and one for outside (e.g. Audio-Technica M50x or something equally portable and maybe more engaging - I use Meze 99 Neo for that use case for example)?. There's really no single answer. I was hesitant to recommend something like my ATH-R50x for indoor use when I saw your comment on r/headphones initially, but they're the king of comfort for indoor use, if you're able to get them around 150 USD. Maybe Fiio FT3-32ohm can be an interesting option on the bassier side, it seems to have a somewhat special driver that approaches planars in detail. To make things easier, based on your previous experience, what kind of sound signature do you prefer (V, U, W, M, flat, bright/warm/neutral-leaning?). For reference, Both ATH-R50x and Airpods Pro are a neutral V, Airpods's V is a little more pronounced, R50x's is a little more mild.. And what do you consider to be fun (e.g. microdetail, emotional bassline, guitars being shredded, etc.)?

I can also vouch that meze 99 classic or neo (neo is cheaper) fit great with glasses.

as another glasses user I've had some offer surprisingly good comfort. Normally on-ears are a bad idea, but my grado sr60x are super comfortable *after I stretched out the headband*, you have to really stretch it out so that it applies almost no pressure to the ears, it's basically floating there, suspended only by the headband. Another is koss KSC75, again, usually having more stuff hooking to the ear is a bad idea, but I can wear these things all day long (which I have done before...). Sennheiser HD600 I was also expecting to suck, especially when I first put them on and felt how much pressure they apply. I still need to bend them a little more to relieve pressure, but even before stretching they applied more pressure near the jaw below the ear than my glasses frame. worth noting I have metal frames with wide (more like tall) but thin (1mm or less) temples, so I can get away with more pressure than frames with thick temples.

The next best thing is their next model the fiio ft1. It is 160$ though. If you can wait and save up I do think it's worth it. The other save up option is a the meze 99 neo which is very bassy and would fit your needs well. I wouldn't trust linsoul currently in my opinion. They make some of the best earbuds on the market but they are still figuring out headphones. In a couple years I suspect they will be an excellent purchase. The ath headphones are very safe and fine. I have had a couple pairs over the years and they have been ok if a little boring. I do love the look of them with 3rd party ear pads and tend to wear them out. The 100$ budget has been a difficult price point in the community for a long time. If you want headphones now, I would get the fiio jt1. Otherwise I would save a little more. I wouldn't hesitate pulling the trigger if you want one now though

Meze 99 Classic or 99 Neo with the Boom Mic package. The mic sounds good and the headphones are really good as well, plus they're repairable. You can also just buy headphones with removable cables and plug the Meze microphone in if you don't like how the Meze headphones sound.

I agree, I have the 99 Neos and they are very comfortable and have the sound signature OP is looking for. I will say that the original ear cups wore out quickly where my eye glasses contacted them. I bought another set of the Meze pads ($20) this time around but I’ll try some different pads if it happens again. I believe Dekoni makes some nice ones. With Black Friday prices I think OP could get the 99s and Dekoni pads within their budget.