I had a pair of Shures that I paid over $200 for. Every other earbud I've tried has been terrible. They're tinny, they don't fit right, and you have to blast them to get over moderate ambient noise. I worked in a fairly noisy office when I had the Shures, and I could turn the music down to one click over 0 and still hear nothing but music. The sound quality was also a lot better than just about anything else I've used (save for my $290 pair of over-ear headphones). I ended up losing them (or they were stolen, not sure) and just never replaced them. I mostly work from home now, and no one here is going to care if I turn up the speakers connected to my desktop.

Were they $300 better, or even $50 or $100 better? That depends on what your priorities are. Me, I've spent a lot of time and money collecting a high-quality music library, and I prefer to hear it through headphones that are transparent and don't lose detail. Your priorities might be completely different.