The Shokz OpenSwim headphones are a great waterproof solution with a secure fit

With full waterproofing, 8-hour battery life, and enough storage for 1,200 music tracks, these bone-conduction headphones are the best choice for swimmers.
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SHOKZ OpenSwim Swimming MP3 - Bone Conduction MP3 Waterproof Headphones for Swimming - Open-Ear Wireless Headphones, No Bluetooth, with Earplug (Black) : Electronics

Shokz OpenRun - IP67 Waterproof Sport Headphones

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SHOKZ OpenSwim - Bone Conduction MP3 Waterproof Headphones for Swimming - Open-Ear Wireless Headphones, with Nose Clip and Earplug (Blue) : Electronics

Buy the Shokz OpenSwim Open-Ear Bone Conduction Waterproof Headphones - Blue ( S700BL ) online

Our top-selling wireless sport headphones formerly known as Aeropex now come with new packaging, a quick-charge feature, and a new name. OpenRun is our lightest headphones to date and are engineered with outstanding sound, a long-lasting battery, and Quick Charge to keep you aware and motivated while you power through any workout.

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SHOKZ OpenSwim - Bone Conduction MP3 Waterproof Headphones for Swimming - Open-Ear Wireless Headphones, with Nose Clip and Earplug (Blue) : Electronics