1. Price: Unlike hi-fi speakers, you'll discover upper tier headphones are a more affordable purchase. Sure, if you've got money to burn, you can spend $5,000+, but most pro-model headphones will cost you between $250 up to $1,500. 2. Brands: If you're willing to invest in some higher-priced cans, here are some of recommended manufacturers: Sennheiser, Grado, Beyerdynamic, Audeze, and Audio-Technica.
3. Choosing the Right One: When it comes to high-end headphones, a determining factor for purchasing is intended use. Are you going to mainly watch movies or listen to music? If you are going to listen to music, what kind? Classical or electronic? Headphones are often engineered and optimized for a certain listening experience. I discovered once I began listening to music with headphones, I found it difficult to go back, especially when compared to standard computer speakers. I personally use Sennheiser HD800's, just beating out the Grado PS1000.
4. Headphone Amp: Hi-fi headphones perform best when partnered with a headphone amp. Without one, you'll find that most of the time the source volume might be too low. That's where headphone amps come in. You can find some starting at $200 going up to $3,000 and more, depending on features/power. 5. Going Mobile: Unless you purchase something like the V-Moda VAMP Analog Converter/Headphone Amp Case for iPhone, it's probably best to leave your high-priced headphones at home. They can be easily damaged and are ideally suited for home-use. Consider purchasing cheaper travel models, which won't make you shed a tear if stolen, lost, or damaged. More About Headphones Headphone Tweaks Woo Audio Tube Amp Cordctrl Cable Organizers (Images: Anthony Nguyen, Flickr member Noelas licensed for use under Creative Commons, and Flickr member Tai-Hua Lu licensed for use under Creative Commons)