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If you are in the market for headphones at this price point, you are likely looking at both of these models. I ordered both, tried them out side-by-side, and returned one. I kept the Sennheisers.
Let me start by saying that I am NOT an audiophile. I was looking for headphones to use with my iphone, that I could use at work at a reasonable volume without disturbing, or being disturbed by, my neighbors with sound leakage. My previous headphones were the inner-ear style, and I found those to be extremely uncomfortable.
Second, I'll say that both the Sennheisers and the Shures are excellent, from a layman's perspective, and that you really can't go wrong with either. Again, a true audiophile would probably tell you something different, and be able to explain the technical side of why one is clearly superior, but I am not that guy.
So, why did I prefer the Sennheisers? The 2 main reasons are:
1. Better sound isolation. Not just a little bit, but a lot. With the Shure 440s, my wife was able to sing along with the song I was listening to at 50% volume from 12 feet away. Compare that to the Sennheiser HD 429's, and I had to get within arms length before she could even hear a noise, let alone be able to tell what the song was and sing along. Further, I had her turn up the volume of the television until I could hear it through the headphones. She got up to 30 with Sennheisers, compared to only 14 before sound started leaking through on the Shures.
2. Better comfort. This is obviously a personal preference, and will depend a lot on your head size and shape, but for me, the Shures felt like they were going to fall off every time I moved my head. The Sennheisers felt tighter, but not in an uncomfortable way. Just the opposite, actually. Then Sennheisers felt secure on my ears, and like it would be no problem to go jogging or working out in them, if I were so inclined.
2a. As far as long term comfort, I wore them each for 2 straight hours. This was a struggle with the Shures, because like I said, every time I moved my head, I felt the need to adjust them, and tighten them just a little bit. However, despite what is said about the Shure 440 earpads being bad and needing to replace them with the 840 earpads, I did not find the standard earpads to be uncomfortable at all. For the Sennheisers, they stayed comfortably secure the whole time, which I liked. The earpads are soft and very comfortable. When I took them off, I did notice how warm my ears must have been, because they felt cool when in the open air again. But I did not notice my ears being uncomfortably hot while actually wearing them, it was only when I took them off. I also found the padding on the top of the head to be more comfortable with the Sennheisers. The Shures started irritating the top of my head after about 45 minutes.
As for sound quality:
Again, not an audiophile. I tested both sets of headphones on a wide variety of music. I like my music to sound balanced, not to heavy on the low end or the high end. The Sennheizers seem to deliver more bass than the Shures. A bit too much on some settings, actually, but by using the "Acoustic" setting on the iphone equalizer, the Sennheisers sound very well balanced to this layman. For the Shures, I found the "Classical" setting to be the best. But you can play around and see what works for you.
Both sets were easily run by my iphone, without use of a headphone amplifier. But, with the better noise isolation, I was able to keep the volume lower with Sennheisers.
If there is one area where the Shures have a clear advantage, it is the wire. The Shures use a thick, coiled wire, like the one that connects from the base of a telephone to the handset. The Sennheisers have a just a long, thin, straight wire. It feels a little flimsier than the Shure wire, and might wrap around something without you even noticing. So, both wires give you the same range of motion, but the Shures do it neater, if that makes any sense.
TL;DR: The Sennheisers are the choice for me. They lost one star for the wire. I would rate the Shures at 3 stars, knocking off 1 for sound isolation and 1 for comfort. But like I said before, that comfort thing is highly subjective. Overall, the sound quality is equal. It is just a matter of finding the right setting for your preference.
Both are great choices for the price point, and I'm sure you'll be happy either way, but for me, the Sennheiser HD 429s hold a slight edge over the Shure SRH 440s.
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