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Headphones or earphones, less than $200

HD280 and the 7506. I have one pair of each. While there is a slight (to my ears) difference in bass and low-mid response, I don't think it's enough to prefer one over the other, but that's just MY opinion. I am glad I own both; the Sony's tend to roll in my kit bag due to size and the Sennheiser's are for the house. I've never had any issues with broken pieces and I hope I didnt' just type famous last words.
 
I love my Sennheiser HD600s - I have 2 pair, bought a second one slightly used on the 'Bay for $160 - very smooth! with a nice clear bottom. I use these on my Tascam CDBT1mkII for quiet practice too.

In-ears I have a Shure E2 (similar to the Ety 6i - live in my bass case), Shure E5 (for in-ear monitoring with worship team at church) & Etymotic ER4 (for iPod use - not sturdy enough for gigging use) - I REALLY Like the Etymotic flanges in ALL in-ears much better than foam inserts. Seals up the ear canal and helps with low freq extension.
 
I decided on the HD280. Just got them yesterday, love them. even sound reproduction is right, these are the clearest headphones i've ever used, and the detail it displays especially in the mid/high end is exceptional, i can hear every little bit of guitar and vocals. Very clear lows, and never overpowering unless the music is mixed to be so. not an amazing sounding high end (cymbals) but I have only listened to mp3s and they tend to make cymbals sound terrible (yes I am the kind of person that hears a difference even on cheap headphones). I'll listen to some CDs or records tonight and I assume the high end will be at least somewhat crisp. The isolation on these is great, about on par with the etymotics. i have had someone trying to have a conversation with me from 3 feet away when i had these on with my ipod at about 1/4 volume.

for the price, these are incredible. I'm going to pick up a cheaper pair for school listening, these are huge and too expensive for me to bother. Maybe those $15 sennheisers will do the trick.

Also, reading some reviews apparently a headphone amp will do this a LOT of good. what should I look into, or could I just build a circuit myself?
 
It all depends on what you want it for. Since this is a bass forum, I'll talk about applications for music, primarily bass. If you just want a pair of street phones, just get a cheap-ass $20 pair and be done with it. You'll just lose them somewhere anyways :)

I did a bunch of research on the net as well when I was in the market for headphones it practice my bass quietly (no shaking the walls here in Japan!).
I went ahead and bought Grado SR80's and an equivalent pair of Senn's. I got home and started jamming with them. After not too long, I realized that the sealed cans are not the best for bass. My ears became fatigued quickly and I got a headache. It wasn't all that loud, either. On the other hand, while the Grados do allow the sound to breathe a little more, I find ear fatigue is much less.
 
Sony MDR 7506. Fantastic for recording. Full coverage (not "open air"). The right amount of bass response. The key word for these is ACCURATE. About $100.

I have a lot of cans, Sonys, AKGs and Sennheisers. I like the Sony 7506. or I use that the most.

I have little quarrel with the Sennheisers, they make good headphones, I still use them - I like the HD250 for tracking drums in the studio. It has a better acoustic seal than the 7506.
 
Yeah. I don't actually mind having open design phones for bus/school/walking. So I might just get some SR60s and have another pair of headphones for recording as well.

What I like about these headphones is how different they sound with different bands/production techniques. The subtleties present in the guitar and vocal tones are much more obvious than I've heard before.

I tried these out with bass, listening through my computer and it sounded good. very full, where the etymotics sounded really thin, especially in the mids. No fatigue either, wore these all day at work yesterday and had no problem.