I never thought I'd see the day when I'd want headphones for running. Not because buying headphones just for running is a bit frivolous, but because I stopped running as a regular exercise a few years ago.

When testing the best fitness trackers and the best smartwatches, I prefer to ride an exercise bike, show up at a Pilates studio, or walk long distances to analyze the metric of activity tracking. Running reminds me of sports careers that have passed and the commemorative pains of sprinting through the outfield as punishment or running miles on the treadmill to stay in shape during the softball off-season.

Recently, however, I have become interested in running again. Not to learn how to train for a half-marathon or anything, but just to diversify my cardio regimen. Besides, running is a popular social activity in my city, and I often reward myself with an iced latte or green juice after a run.

I headed to the track last weekend because I knew I needed to get in a workout on my own before indulging in overpriced drinks with my buddies. I prepared properly by wearing supportive sneakers, replenishing electrolytes, and stretching beforehand.

So it's a shame that the experience was ruined by something as trivial as headphones (which are also quite pricey).

When I go for a leisurely stroll, I often opt for the AirPods Max, which have active noise cancellation and good sound quality. However, they are not sweat-proof, so for hectic commutes and power walks, I rely on the classic Apple EarPods (when they still came with the new iPhone).

The wired, tangled buds are a pain to run with. I parted ways with my wireless earbuds last year, but I still use my AirPods Pro when I'm not moving around to listen to music, such as during work meetings or train rides.

So I'm not sure what I was thinking when I brought the AirPods Pro on my first run, probably because I read an article about a workout test of the AirPods Pro that showed Apple's high-end earbuds stayed in place during high-impact exercise. But even though I knew my proper fit thanks to the ear-tip setup process, I spent half my time trying to get back the buds that fell off on the track (which bounced around quite haphazardly depending on how fast I was running).

Despite my rocky start with no soundtrack, I am now determined to find the best running headphones that won't pop out of my ears with every step I take. Over the next few weeks, I'm going to try things out to find the right headphones for me and to motivate me to keep running.

Here are the running headphones I'll be testing and why they made this list.

Will I find the perfect running headphones? Stay tuned for hands-on tests of all the models above. I'm not the only one who needs the right gear to get the most out of my workouts.