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Anyone got any product recommendations? I'm willing to spend up to $100 (thanks to office holiday gift). Looking for good audio quality, minimal leakage, secure fit. Comfort, too, would be nice.

I really like Sennheiser's stuff. I haven't tried any of their lower end under $100 products, but they make great headphones in the higher price range, which I would hope would translate down.

for something that's a good all-around headphone, i've been using monster's iSport for the last few years. i can wear them drumming (lots of sweat) or on a plane and they sound good. lots of different earpieces come with them for all sizes. i found out with these that one ear has a smaller opening than the other. these work with that they are right at the $100 mark and have lasted much longer than the few $70-ish headphones i had before this. they have a flat cable to prevent tangling, too.

edit: i just looked and it looks like they have changed the style quite a bit, so i can't vouch for the current model, but i can say that it looks like you can get a pair for $40 right now at amazon:

As someone who spends about $10 on eardbuds from Skullcandy (and loves them), I'm too embarrassed to even answer this question...

I usually have gone the low-cost option, but then you get what you pay for.

I have these and like them a lot: http://amzn.com/B004P7O26W

I had the previous generation of those too, but they finally died after about 7 years of regular use. The sound is good, not excellent, but the noise cancelling is really nice when I'm on the light rail or a plane. They're much easier to carry around than a pair of the big Bose noise cancelling headphones.