It can be hard to find headphones that fit your ears and make sense for the style of training you like to do. Rebecca Brown, senior editor, recommends the Bose in-Ear Headphones/Earphones ($300) for running.
"I have struggled my entire life to find the right headphones for running because they always slip out of my ears. And with the added mask around my face this year, my usual use-a-sweatband-to-hold-the-earbuds-in-my-ear trick wouldn't work — there were just too many elastic pieces going every which way. I splurged on these Bose in-ear headphones and they've completely changed my running. For whatever reason, they NEVER slip out of my ears and they've enabled me to focus on running instead of fiddling with my ears the entire run."