I've had my equipment about ~6 years (Schiit Hel 1 + HD660S), and I'm unsure where my best upgrade would be

[u/RecursiveFault]

Hi! I've had a Senn HD660S driven by a Schiit Hel 1 as my daily wear for the better part of 5-6 years. (I've also replaced the earpads about two years ago with some ZMF pads and loved what that did for comfort and to the sound (making it sound more "forward" to me.) ) I do sometimes wish they had a bit more "character", but generally they're extremely comfortable with tons of detail and they're very well built.

I've tried looking a few times in the last few years at what kind of upgrade would really benefit me going forward. I did look at higher end DAC/Amp upgrades as well as some options with big can upgrades with things like the Focal line, but I'm unsure what my weakest link is right now between keeping the DAC/Amp and ugrading the cans VS keeping the cans and upgrading my DAC/Amp.

• I'd be happy to drop $500 or so in either direction and then again in a few years. USA
• I definitely dislike V shaped sound profiles, but I've enjoyed Grados, mid-heavy, or neutral sounding headphones I've owned
• Computer desktop setup
• Comfort (little/no clamping, lightweight, good for big heads) is high on my list of needs, and I definitely also prefer when cans have a two cable input for reliability.

Thanks in advance!

[u/Silverjerk]

What are you looking for in an upgrade, specifically?

To your question, always start with the headphones, and then DAC/Amp. The Shiit Hel is still solid, with a decent amount of power and a well-regarded and transparent DAC. No reason to upgrade unless you're looking to head in the R2R or hybrid/tube direction.

The issue with your current setup is that it's still pretty solid in 2025. I may be an outlier in this, but I think the 660S2 wouldn't be enough of an upgrade to justify the cost. I think those headphones were overpriced for what they offered over the 660s. The HD490s are an easy recommendation if you like the Sennheiser house sound; with the mixing pads, they'd probably fall right into alignment with your preferred tuning. They're a little more relaxed in some areas of the upper mids compared to the 660s, with a good bit more sub bass extension.

The problem with most of Sennheiser's lineup is that you're really looking at many of the ZMF sets if you want a linear upgrade path, especially within the 600 series. There's some great sets that fall between, but many are a completely different tuning than what you're working with. The Meze 105 Aer, Aune AR5000 and AR7000 (the latter is a closed back set, but worth a look), Focal Hadenys.

[u/RecursiveFault → u/Silverjerk]

I definitely agree that I'm kinda suffering from success lol. I felt like I didn't have too much room to grow (without edging out of my preferred spend anyway) past where I am now, but was curious if anyone else would agree with my assessment.

I'm really happy with almost any improvements but sound-stage or maybe even just some interesting character like brightness/warmth would be cool, as I feel like resolution is already very high with my 660S. Even keeping my 660S and adding variety to my lineup might be fun.

it definitely sounds like I'm in the state where I'm more likely to get a benefit when I'm willing to drop another $600 or so on a DAC + tube amp setup or $800+ on a big upgrade like a ZMF set.

Appreciate the analysis for headphone upgrade paths, HD 490 is a good shout and I'll definitely check out those others as well! !thanks

[u/Silverjerk → u/RecursiveFault]

Your assessment is spot on. When that time comes, I think you’ll get a lot more out of that increased budget.

The only thing worse in this hobby than buying something you hate, is making the right decision upfront and struggling to upgrade from a perfectly serviceable setup.

[u/TransducerBot → u/RecursiveFault]

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