[audiophile-ish]

So I've been an IEM guy for several years now and I wanted to explore the over-ear/on-ear side more. However, I tried my sister's AKG K181DJs and found them to be very uncomfortable with my glasses. I'm at my computer pretty much all day, glasses on and music playing so I'm looking for something that can be comfortable for several hours of listening at a time. The majority of my music collection is electronic, house, chillwave, and such (I'll link an example below). It's by no means the only music I listen to but since it makes up so much of my listening I'd like something with punchy, responsive bass. If anyone has used them, the Shure SE215's I owned did a good job producing an engaging bass without sacrificing overall clarity that I've experienced at least so something similar to that would be cool; I really can't stand something like the super heavy, distorting bass that muffles the rest of the experience like what I've heard in Beats IEMs. On a very cursory search, the Sennheiser Momentums and Urbanites caught my eye. I'd like to keep it around $200 but I can go as high as $300 right now. 
 
More generally, I'm largely unaware of the pros/cons on-ear and over-ear headphones bring to the table, especially for a glasses wearer, so some education in that department would be appreciated as well. From what I imagine, an over-ear would offer better isolation but an on-ear would be more comfortable for a glasses wearer? 
 
Thanks!
 
https://www.youtube.com/watch?v=Ob3InTwf7t0

 

[billybob_jcv]

I wear glasses. I think it really depends on the entire ear-head-glasses-headphones system interaction. There seem to be a lot of variables - the thickness, shape & diameter of the pads, the clamping pressure, how the cup rotates, the stiffness of the pads and your eyeglass frames, etc, etc. One of the rather annoying things is when the headphones make the eyeglasses sit slightly askew. I have progressive lenses, and if the glasses aren't sitting right, it messes with my normal focusing.

To be honest, IEMs are a lot easier...

 

[ProtegeManiac]

Just to add, a lot of it depends on how your glasses fit. I always wear a certain style of glasses, with ear pieces that are thin and stay flat on the head near the ears but bulge out a bit near the temples (I had glasses before that sat on my temples, and it itched - it got worse as my sweat accelerated rusting on it). The only time I've had a noticeable problem wearing headphones was with a tight-fitting XB500.

 

As for IEMs, I've only really liked the ones with a shell design like Shure and Westone (including my beater IEM, an M6P), or something similar to a custom shell, like my ASG-1. Others wearing glasses don't like these because they have issues fitting the cable with the earpieces on their eyeglasses, but I never had issues with it (I suppose those with flatter earlobes are more likely to have fit issues).

 

[audiophile-ish]

I wear Ray-Ban Clubmasters so the arms aren't too thick and they're not metal. If it helps with recommendations, I tried out my dad's Bose Quiet Comfort 15s (they're over ear) and they were extremely comfortable - I couldn't feel them pressing on my glasses at all. However, the sound was far too weak.