Earbuds Recommended - Apple EarPods This is probably the most common variety of headphones, but finding the right fit can be tricky. Some ears, like my own, just have a hard time holding them in — either being too large or too small. They're often inexpensive and are good starter headphones for casual music listening. I think the new Apple earbuds are fantastic and a heck of a bargain at only $29.00. I did a side-by-side comparison with these earbuds against others and the clarity and dimension they provided was clearly on another level.
Over-Ear Recommended - B&O A8 Earphones Over-ear headphones are a new variety that is well suited for working out and outdoor activities. A loop or clip wraps around or locks into a part of your ear, with the headphone speakers resting outside. The buds aren't as susceptible to falling out, and because there isn't a tight seal to the ear I feel these are more safe for running outside, as you'll still be able to hear oncoming traffic and other sounds. For this type of headphone I like the B&O A8 Earphones; you get great quality sound, and durable construction that will last. Some people find the loops or clips annoying after extended wear, so try some out and take note of how they feel on your ears.
Lightweight Headphones Recommended - UrbanEars Plattan These are good for those that want great sound quality in a comfortable non-obstrusive form factor. They offer decent sound, often better than in-ear varieties, and the comfort straps make them easy to enjoy for prolonged periods of time. UrbanEars delivers a great product in this category, and they come in a rainbow of colors that'll fit your personality. These are great everyday office headphones.
Premium Noise-Canceling Recommended - Fanny Wang These are my personal set of headphones, and I give them rave reviews. The padding is comfortable, the construction is solid, and the noise-canceling features are effective — a practical necessity for air travel. They also fold up for easy storage. Go for this style of phones if you want uncompromised sound quality and complete isolation within your music. Which headphone style best suits you? (Images: 1, 3. Bang & Olufsen 2. Apple 3. Urban Ears 4. Fanny Wang)