Too often the weakest link in a portable audio setup is the headphones
Many portable music enthusiasts spend a great deal of money trying to improve on the quality of their music by buying the highest quality CD players, MP3 players, stereos, and speakers. Then they spend most of their time listening to their portable audio devices through the cheap headphones that came with the devices or something they picked up at the local discount store. Good headphones should be the primary concern in most cases where portable audio quality is a primary consideration.
The cost of headphones
The good news is that great quality from headphones is much less expensive than getting great quality from the other audio components. A good set of headphones will often provide you with a better sound experience than a very expensive set of speakers. So if you're going to spend for the best audio quality, the primary concern should be on purchasing great headphones.
Many people make the mistake of not even buying headphones at all. Almost all portable audio devices now come with their own little headphones. In most cases these are not even brand name headphones, but rather mass manufactured headphones that have a market value between $1 and $10. Even when they are brand name headphones, they are often at the bottom of that brand's product line. Using these headphones greatly compromises the sound quality of the music you listen to on a daily basis. So as long as you're going to invest in a portable audio player with all of the features you want, invest in a good set of headphones as well.
Headphones and location
Primarily we use headphones so that we can listen to music wherever we go without rudely imposing our music preferences on those around us. Think about the various places where you listen to music and where you would like to listen to music. How much better does great sounding music make you feel about each of those places? If you're going to take your music with you, make it great.
These are not your grandpa's headphones
Headphones were once big metal, wood, and then plastic speaker systems that hung on giant headgear on top of your ears. Over time they got smaller, became more comfortable, and provided better sound. This trend in headphones continues today. While earpieces have been available for a few decades now, the moderately priced earpieces we have now provide sound quality that only the best speaker systems of the past could compete with today. But that doesn't mean you should settle. If you can have the sound of a concert hall, why settle for the sound of bad headphones? Take a little time and spend a little money to make sure you get a great sound experience from your portable audio devices with a great set of headphones.