What head phones do you recommend? (250-350$)

So in my budgeting with new position at work I want to treat myself to an upgrade this holiday season.

Currently I have a pair of ath-m50x and they've served me well, but I'm wanting more.

I love the fairly balanced sound they have. The curve was fairly flat and allowed me to edit the curve in foobar to my liking.

I'd like something similar but maybe with something more in the treble. What do you recommend?

buy used.

HD600 would be nice and flat as well.

HE-400(s, i origianal) would be nice too.

Do you have an amp?

I do not. Do you recommend one?

If you do not have a good DAC or DAC/Amp combo unit, everything will just sidegrade you.
I have Sennheiser HD600 for listening to music with my HiFi system. On my PC they sound not as good. Get some reasonable DAC first.
Cheap but decent ($80):
Creative Sound Blaster X-Fi HD
Mid range ($300):
Mayflower Electronics Desktop O2
High end ($800):
Marantz HD-DAC1
What I have on the way (380€ = $550):
Marantz PM6005

Yes, absolutely.

A good DAC + a good amp will cost you around 200,- used. I can recommend the FiiO E09K, I got mine for 80 Euro. The successor to it is the K5 which is supposed to be slightly cleaner sounding but a bit less powerful.
As a DAC you can go for an ODAC or something in that price range. My Musical Fidelity VDAC II is also pretty good.

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I hear the term "Trebble Cannon" attached to the DT990s, which are often highly recommended. Is it "Better" than an M50x? I dunno, I think they're more comfortable?

The 250 ohm DT990 with a DAC/AMP would be interesting, perhaps?

Also we (Antlion Audio, the ModMic guys at which I work) just reviewed the HIFIMAN Edition S, which is a really interesting pair at 250.

They bring some interesting options to the table since you can use them in both open and closed back, sounds great, but again, I feel it will largely be a sideways move from your M50s.

Sadly, at ~250-350 USD (which is probably about what you paid for the M50s) you're starting to hit the diminishing returns where spending more produces a very small gain. I'd agree with everyone else that a DAC may provide more quality than anything else, as if you're using on board audio drivers or even a soundcard you may be getting more white noise and interference than you think.

So ... TL;DR, start with a DAC and see if you can tell the difference and/or get some DT990s or others and see if they are simply more comfortable. I like my M50s, but they honestly hurt my ears to wear for extended periods of time (which was why I upgraded to the R70s - which I guess also fall into this price range, albeit just barely)

I really like grado cans myself for that price point you could get the SR 325E or go with a SR80 or SR125 driver and then swap out for some wood cups (will change the sound a bit depending on what you get) tends to make them sound more like the RS line

The grados are a really love it or hate it sound. I would describe them as flat and accurate with a warmth in the high end.
I would find you a freq chart to help but the headphone rooms' website who does most of that for the cans on the market is down for maintenance at the moment.

I personally really like DIY or mod can setups. so something like these work well for a grado like sound.

The Ypsilon Headphone Drivers and would Cups you could get from http://www.ellevenacoustica.com/products
apparently are pretty darn good. ($90 for the pair of drivers and 76 or 102 bucks depending on the wood cups you like but there are a lot for guys amking these wood grado like cups and doing the grado mods and driver swaps.)
Or turblent X drivers work great too or the sennheiser pxII drivers too apparently.

This might help here also: