I have had my Sennheisers for over a decade now and all that needed to be replaced were the cables and ear cushions. They're nice but since phones went the way of Bluetooth I switched to Ultimate Ears FITs and while the case has gotten banged up they've still served me well since I got them.

I would probably also recommend IEMs at this point, but for earbuds with a more custom fit I like to recommend UE as a brand because they have an app that lets you tune the sound quality, and pretty much all their headphones have a custom fit. I chose the FITs because you can buy light activated gel tips and replace them if your ears change for whatever reason (swelling, injuries), they sent me the smallest size free of charge when I commented that their standard size didn't fit my ears (too big) long term. Because they mold to your ear they're a great fit. UE also just has a good balance between sound, fit, customer service.

I think their drops model is the new kid on the block, it comes with an impressions kit that you send back and they make it for you. But otherwise UE 5 CSX is their consumer level IEM that comes with Bluetooth and wires that you can swap out depending on your use case. I haven't really gone that route because I'm happy with my FITs and you have to go to an audio engineer to get fitted, I think.