The portable listening revolution is fully underway. From open earbuds to noise cancelers and wired headphones, I can find a reason to love them all.

You might think you’ve got enough headphones. Most of us have accrued at least two or three pairs over the years, and might have a few more half-working pairs stuck in a drawer somewhere. But I’m here to tell you, if you haven’t fully explored the fabulous world of specialized headphones that has exploded in the past decade, from open earbuds to sports and travel cans, you’re not maximizing your sonic potential. The best headphones are now so varied that they often depend entirely on what you intend to use them for. That means the best headphones for you probably come in many shapes and sizes, and you might actually want more than one pair.

Balling out on lots of headphones for every one of life's situations doesn’t necessarily mean spending a lot of money. Unless you’re successfully riding the “boomcession,” there’s ...