Whether you're a new or seasoned city runner, running in a fast-paced city like Chicago or New York City is no easy feat. There are cars at every turn, bikes whizzing by, and pedestrians everywhere, which is why you need a solid pair of headphones that won't audibly block you from your surroundings but will still get the job done. The waterproof AfterShokz Aeropex Open-Ear Wireless Headphones With Sport Belt ($160) are unique because of their open-ear design. Instead of sitting inside the ear, they go over the ear and rest on the cheekbone. Now, you can jam out and still be fully aware of what's going on around you.