It's been a while since I had the SR60/80 which I think is the only (relatively) decent headphone that Grado makes. Every other Grado I've bought, all the way up to the current flagship, have been relative disappointments. They are dynamic and they are pleasant - but they aren't very capable. It's interesting to see the Grado comments here as I think that Grado is the "audiophile's" Bose. In addition to the sound they are rather poorly built, trade on their looks/name/heritage, not to mention completely impractical for use on iPods.
The infamous Triports in fact have a little more going for them in terms of portable use - while I feel rather sorry for anyone who praises their sound, they do sound acceptable-to-OK for most, they are closed, they're more comfortable, more practical and are just as (not) durable as the SR's.
There are certainly better or more practical alternatives from Sennheiser and AKG for either the SR's or the Triports. The Sennheiser HD25 and the AKG K81DJ are well-reviewed headphones which are closed, compact and durable.
The PX200's are good, provide some blocking of outside noises but generally sounds a bit dull - the penalty of closed headphone design in such a small space. The PX100 is good sounding but not closed like the 200. I sometimes stand next to people with them on the train and how much they're blasting the music out causes a bit of concern. Excellent for use in cubicles, etc but not suitable for urban use if you ask me. As others say, both are surprisingly durable.
There's also a new pair of headphones from Sony.
http://www.sonystyle.com/is-bin/INT...ductSKU=MDRD777LP&DCMP=Redirect_ss_MDRRD777LP
The D777 has an ambient sound in switch. The headphones that the D777 was based on (the Eggos: thus named because they collapse into an egg-shape as the D777 also does) had a facility to let in ambient sound, so that you could hear train announcements or road traffic. The new D777 has a switchable valve so that you can select between fully closed and 'ambient-in' modes. The flagship Eggos have always sounded pretty good and this promises to be no exception. It's $30 over the OP's budget but may be worth a look - should be in stores now.
Er... sorry about that, post ended up a bit longer than I intended
