If you like listening to tunes while you run, train, or play, you've probably had your 'buds fall out of your ears at least once or twice. Yurbuds Ironman Earphones ($50) are designed to eliminate this problem by using ultra-soft, medical-grade silicone tips that provide a snug fit, while other features like neodymium drivers and a water resistant design provide superior sound and toughness. Included in the package are a red Ironman nylon carrying case and some Ironman trading cards. Time to bust out that Beckett.
For those who wear headphones in more extreme environments than in a lounger next to their hi-fi, durability often trumps sound quality. These Philips O'Neill Stretch Headphones ($70) aim to offer both, featuring an impact- and crack-resistant stretchy headband, tangle-free cabling that separates from the headphones to prevent breakage, soft ear cushions for all-day comfort, and dynamic 40mm drivers for great sound.