Total budget (max).
Closed or open back.
Genres of music/movies/games.
What you favor in sound (bass heavy, neutrality, treble heavy, bright treble, or dim treble).
What source you're using (ie, phone, computer, soundcard, etc, whatever you're plugging into).
I'm thinking around the budget for these phones I've listed (e.g. 250 maximum).
Closed would be preferable but my 495 is open back. I think the 598 is too?
I like comfortable and I like Sennheiser. I'd just get the 598 except it's at the top end of my price range and there are probably better-sounding cans for cheaper.
HD 558?
Music - I'm ashamed to admit this but I use my 495's mostly for gaming. But music, well female vocals is my main use case.
The forward upper mids work wonders. Just make sure your head fits. If you need to use the max slider adjustment on anything else, I'd recommend against for comfort reasons.
I've also heard good things about the HD 598 and female vocals, but I've never actually heard one.
What I would really like to recommend would be a used HD 580 or HD 600 for better comfort and scalability, but those require amping to sound their best.
I'm not in the market for used. All of these things are available in Singapore at inflated prices, but I will be in NYC in a few days and will visit the fabled B&H. They have the 598 for $250, the DT880 for $235 (yeah, cheaper than the 598). Of course the ATH-M50 is less ($170? same as HD558). They also have the AKG Q701 for $240 - but it doesn't look as plush as the 598.
Will note that my audio source is predominantly MP3 albeit at higher bit rate. They say the 598 is not detailed enough to expose the quantization errors in MP3 and is therefore recommended for that purpose..?
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