Ah, the Sennheiser HD-580! This is an elite headphone, with quite a reputation! For many years, the Sennheiser HD-580 has been lauded by stereophile magazines for it stellar sound quality and durability. It’s a comfortable set of ‘phones with soft, velvety earpads. It has a metal band at the top — lesser headphones have plastic instead. It sells for about $120 today — and that’s a bargin (it used to retail for $300).

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The Cordster is a small attachment to keep your headphone cables untangled. It works with virtually all portable cords, and snaps on and off using a removable Velcro-like fastener. Reportedly, it works well. Available in a variety of colors for $4.95.

Recommended
by: CNET, StreetTech.com,
Etown and Consumer Guide

From CNET:

The Grado SR60 headphones are made in Brooklyn–and they look it. Their black-plastic design doesn’t exactly exude high tech, but as soon as doubters hear the SR60, their objections usually melt away. Converts gush about the headset’s rock-solid bass, extraordinary detail, and clarity. The SR60 has been on the market for more than 10 years, perennially garnering raves in audiophile magazines around the world. It retails for $69.

The SR60’s earpieces have large cushions, but we’re not about to claim
that these headphones set a new standard for wearability. After spending
a few hours with all that foam clamped over your ears, you’ll need a break.

For listening on the go, the SR60 is our hands-down favorite among sub-$75 headphones, and it worked fine on our home system, too. For a mere $30 more, you can enjoy better bass and detail on Grado’s SR80, which uses a slightly higher-quality cable and larger ear cushions. The SR60’s cord is fitted with a gold-plated miniplug, and Grado supplies a gold-plated 1/4-inch adapter.

The SR60 stomps all over the pathetic little earbuds that come with iPods. After a one-minute comparison test, you’ll never want to go back to that tinny and distorted sound. And here’s more good news for owners of portable MP3 players: The SR60 is extremely efficient, so you’ll be able to listen to your files at louder volumes than on other headphones.

Best Price: $55 (Ebay)
or $69 (Cambridge Soundworks)

• Universal
  fit design
• Outstanding
  bass response
• Outstanding
  vocal tone
• ComfortEar™ custom
  fit sleeves available (at additional cost - ear impressions required
  for this option)
• Great
  upgrade to similar systems

Response:
20 hz to 20,000 hz
Driver: FSI proprietary F/R
Impedance: 32 ohm
Sensitivity: 118dB
Isolation: 25 dB
Cable: 45″ standard
Connector: Standard 1/8″ Stereo Gold Plug
Accessories: Carrying Case (Pouch Type)

Best Price:
$143.10 (FutureSonics)

Blocks external noise with comfortable sound-isolating sleeves that contour to the inside of the ears.

Shure E3c Sound Isolating Earphone -
The replacement of the acclaimed E1, the E3 uses low mass, high energy micro-speakers
to deliver incredibly precise sound with secure, comfortable, acoustic isolation
for an outstanding listening experience where ever you are. Whether listening
to your home stereo, computer, or portable CD or MP3 player,
this earphone offers studio-quality performance of the highest order.

• Smallest of Shure E-series Weighing only 0.9 ounce - less than 1 ounce
• Instead of bulky headphones, E3 wearers get form-fitting earpieces
  that stay securely inside the ear without uncomfortable headbands
• Sound isolation prevents outside noise from interfering with the music,
  and creates a quiet space for exceptional Audio clarity
• The studio grade, low mass, high energy micro-speakers employ balanced
  armature technology for more efficient Output and
  extended high frequencies
• Compatible for use with 1/8 inch (3.5 mm) audio output ports
• Includes carrying case
• Soft, flexible sleeves in the Fit Kit gently contour the inside of
  the ear for a comfortable, secure fit
• 60-Inch cable with Gold-plated connector
• 2 Year Shure Warranty

Best Price: $179 (B&H)

Recommended by: ZDNet, CNET and Wired Magazine.

From ZDNET:

The name Etymotic means "true to the ear" and is pronounced "et-im-oh-tik." We’re huge fans of the company’s ER-4P headphone set, but it retails for a whopping $330; the ER-6 Isolator, meanwhile, carries a list price of $130 and is designed to offer most of the performance and features of its pricier sibling for a lot less money.

The ER-6 comes with both silicone rubber and foam eartips, which the user can swap. They’re designed to fit into your ear canals, like earplugs, to block out ambient noise. We judged their effectiveness to be the equal of active or battery-powered noise-canceling headphones. There’s just one caveat: some buyers, particularly those with smaller ear canals, may find the eartip insertion rituals a bit daunting or unpleasant (you really have to jam them in). Also, the rubber eartips in particular have a tendency to attract earwax and will have to be cleaned regularly. But this reviewer found the ER-6 to be highly comfortable–arguably more so than other top in-ear headphones, including the Shure E3c or the Etymotic ER-4P. On the other hand, some CNET editors preferred the fit of Shure’s E3c and Sony’s less expensive MDR-EX71SL.

As with those in-ear models, when we walked or moved, we heard the ER-6’s wires rubbing against our clothing. You get used to the sounds over time, but they’re there, and the ER-6’s very thin and superflexible wires are prone to tangle; ours did, even after we carefully stowed the headphones in their carry pouch.

Ah, but the ER-6’s sound is extraordinarily fine. Because of its noise-isolation attributes, on a roaring NYC subway train, we were able to listen to our iPod at very moderate volume levels; we didn’t have to blast our ears to enjoy our music. Then again, if you want to play loud, the ER-6 can achieve fairly high levels with a portable MP3 player, though the ER-4P was able to play louder.

Listen, and you’ll hear a purity to the sound that few ‘phones can match; we were constantly surprised by the ER-6’s ability to resolve even the most subtle details of our music collection. Bass response is excellent–deep and well defined–for an earbud-type headphone. Bass buffs will be happier with a full-size Grado SR60 ($69), our iPod headphone champs. However, overall the ER-6’s sonics are cleaner and far more resolved than the SR60’s. As always, your buying decision is a matter of identifying your priorities.

Available from: Amazon ($99)