The important part of headphones doesn’t advance as fast as technology and construction elements. A dac will advance but a tube amp or well made drivers will probably still be great.

Headphones, debatable, but IEMs, the difference is night and day. A good $30-40 set like the Cadenza, Hola, 7hz Zero, etc. in 2023 absolutely trounces $100+ sets from 5-10 years ago. Then you’ve got your $1000+ tribrids and whatnot. IEMs are where the innovation is at.

Idk about headphones but IEMs have gotten exponentially more advanced the past decade.

Even these last few years have been night and day differences like the Campfire Audio Andromeda from 2016 to the 2018 ThieAudio Monarch lineup and now the crazy Elysian Annihilator, Fir Audio XE6, Empire Ears Raven, FatFreq Grand Maestro, to name a few. I can’t keep up!

They gotta chill with the prices though as flagships are costing as much as $8000. I’ll wait it out till I can get the Annihilator in a few years for $1000 lol

Back in 2009 I was into headphones because the HD600 or HD650 were so much better than any full size speaker system that I could afford. Even a few years ago, both headphones paired with decent DAC and amp were much better than a speaker system costing 3 or 4x.

A few months ago we were testing systems and the headphones were not in the same league of a 4x speaker system, and I understand the Senns hold their ground against mostly any headphones in their price range.

I thought this experience was relevant to your question even when not directly answers it.

Comparing different headphones, then there isn’t much difference between a new headphone and an old one. I have AKG headphones from before 2013 and they are still amazing. Old AKG and Sennheiser headphones are still good.

The difference is within in brands and mostly planars. I haven’t heard all of them, but people say every version of the Hifiman Arya was noticeable better than the one before. DMS didn’t say it directly, but he said newer Audeze headphones have better tuning than the one before while maintaining their technical ability.

The problem with that perception is that there’s no linear way to measure improvement in the space as there’s no objective way to declare a “better sound”. It’s not like a cellphone that can claim x16 speed, x10 storage.

Also don’t forget we’re getting improvements in the space, while entry level headphones have barely improved now have sub 200$ planars, Audeze is doing 300$ gaming headsets, headphones are using newer technologies in their drivers. It is no longer a Sennheiser vs Beyer / Audio Technica, now there’s a lot more options.

10 years ago is not that much in the headphone world. It’s not a market where there is that much demand. Very different from the current iem market. A 200 pound headphone from 10 years ago will be superior to a cheap headphone from today generally speaking. Build quality is definitely also a factor which, if anything, has gotten more expensive to do well. The best deals to be had on headphones would be second hand ones. Especially less known brands, but even sennheiser headphones can be had for absolute deals. I paid like 70 euros for my hd560s. A sundara is around 200 euros, a hd700 goes for like 300-400 euros and is (IMO) basically 80% of an hd800. Speaking of which, I got my hd800s for 800 euros and you can find the normal hd800 for around 600-700. Keep in mind that these are all headphones that are still considered very competitive at their new price points which is on average around twice the secondhand price. I would argue that for iems the secondhand market doesn’t make that much sense unless you can find modern products for good deals. Especially when many companies do such aggressive discounts so often.

It depends on the headphone and the market. 10 years ago, the hd560s hadn’t been released yet, while now it’s one of the best for the price, if not the best, at least in the EU market, while in the USA the 6XX was released prior to the hd560s and depending on taste it’s arguably a better deal for that market. Koss 60 ohm lineup has been out for quite some time, and they’re a pretty good deal and probably we’re just as good when they were released. The hd600 has come out in 1997 and for that kind of sound it is to this day the best deal to get it. Then you have the recent hifiman that have come out in the last 10 years and are a pretty good deal and compete well with what’s available today, yet the quality control is still not up to par. I’d say the golden age for headphones happened around the 90’/2000, since most models that come up today have to make up to the good reputation of models that came out in that period. Some stax headphones came even before that, and for some specific aspects they’re still the best, even though new models have come out. I’d say there isn’t a general rule of thumb for this, it depends a lot on what is considered “good” and what price range you’re looking at. Still, some pretty good headphones have come out in the recent years, and some pretty good headphones from the last decades are still relevant today, but there’s still a lot of junk being produced today, as there was some decades ago. What’s true is that good models stay good, no matter when they came out

Moondrop Blessing 2 would obliterate Sennheiser IE8 and UE TripleFi 10.

Try 25 years. The Sennheiser HD600 is still considered great.

I will say that there’s a way better selection of great headphones now than pretty much ever, but things largely haven’t changed. Planar headphones were the biggest thing to happen since then and they’re not necessarily better than old dynamic drivers, just better at different things.

At the end of the day, a headphone just turns squiggly electric waves into a medium that wiggles and pushes air in ways that make noise. Tech advances don’t really do much to change that basic concept.