Not gonna lie, I don't generally find IEMs to be particularly comfortable, at least with heavy use. Doesn't matter what size tips I use, unless I want them falling out, my ears are going to be sore if I wear them all day. I prefer to use lightweight over-ears any time I can. I can wear my HD 58x all day and barely need to adjust them. My ATH-M40x on the other hand can feel a bit heavy after a while so I don't wear them much anymore. If I want something really flat I'll use my speakers.

Even started using my 58x at work/outdoors powered by my phone, and the drop in sound quality is hardly noticeable to me. Maybe 5% worse bass perhaps but that could very well be placebo.