[shnitz]

You can custom order Beyer DT880 for $200.  You won't find more comfortable than these, there never have to be excuses about the comfort.  Choose the 32 Ohm version.  Get the velour pads.  As far as the color combination, choose whatever you think looks good.  You won't need an amp for these, just like with the Grado.  The Audio Technica ATH-ESW9 are pretty stand-out.  Not trying to say that the Grado are bad in any way, just trying to give you more options.  Take it from someone that's been there, just choose one that seems good to you.  If it's been recommended here on the forums by countless people, then it's going to sound good.  A large part is just personal preference, but you'll never be able to build those preferences until you start listening.  I promise you that this won't be your last pair of phones.  I started with AKG K240 Studio, and while I've sampled many others, they are the ones plugged in to my computer right now. Comfortable enough to wear all day, and they sound amazing, better than my Ultrasone 650 (although I still have these in the rotation too).  The K240 Mkii even adds more quick-connect cable choices, plus an additional set of earpads, made out of the same material as the Beyer: velour.
 
My advice: Take that first $100 and invest it in a decent amp.  You may hear a difference, you may not.  But people have been happy with cmoy built by biosciencegeek and jds labs, both available through ebay.  Or, the Nuforce uDAC and Fiio E7 have both gotten rave reviews.  You can always sell these locally if you feel they don't add anything to the low-impedance headphones.  Take the other $100-$300 and grab yourself a pair of cans.  Search this forum, your exact question comes up multiple times a week.  Sometimes the musical preferences or budget slightly changes, but it's the same overall.

 

[stang]

Personally, I wouldn't get a DT880 unless I could get the 600ohm version AND a good amp. If your budget is around $400, I wouldn't get something as difficult to drive as the HD650, DT880 600ohm etc. While 32ohm won't be as hard to drive as the 600ohm, it doesn't sound as good (most will agree, but you must remember that different people have different ears).
 
Grado's aren't the most comfortable, but I feel that for a person with a pretty tight budget, they can be a great start. SR-225+uDAC+Little Dot I+ would be a great starting point, providing you can find all that for around $400. Used, it shouldn't be difficult at all to find those at under $400.

 

[Mr Joboto]

I find Grados very comfortable. And they make great unamped headphones. Look into the MS1i or the SR225i.

 

[rusitnpiece]

Grado SR-125i were my first 'audiophile' headphones. They sounded great with the sort of music you like. I only sold them due to the issue of comfort. It seems though that you either find them comfortable or not. Try them out. You may have found the headphone for you. Don't let money be an issue or deciding factor. I have searched around and spent lots of money in the past and end up using my headphones that you can buy for around £60. I wish you all the best in finding your ideal headphone.

 

[shnitz]

Quote:

Personally, I wouldn't get a DT880 unless I could get the 600ohm version AND a good amp. If your budget is around $400, I wouldn't get something as difficult to drive as the HD650, DT880 600ohm etc. While 32ohm won't be as hard to drive as the 600ohm, it doesn't sound as good (most will agree, but you must remember that different people have different ears).
 
Grado's aren't the most comfortable, but I feel that for a person with a pretty tight budget, they can be a great start. SR-225+uDAC+Little Dot I+ would be a great starting point, providing you can find all that for around $400. Used, it shouldn't be difficult at all to find those at under $400.

Funny how the first article in the "Sound Science" forum seems to be about this very thing:
http://www.head-fi.org/forum/thread/506963/dt880-600ohm-bs
 
Personally, I don't feel you are missing out getting the 32 Ohm. They sound amazing.  My friend got them to replace his Sony V700DJ once I put the Sony's up against my AKG K240, and the AKG destroyed them in every respect, even DJing.  Two weeks later, he started carrying the audio bliss that is DT880 into work with him.  According to Headroom's graphs, all that seems to suffer is the capability of playing the very low frequencies, and they seem to only suffer slightly.  Otherwise, it seems that one would be hard pressed to discern a difference, and especially not a person new to this hobby.