questionschallenge: ear-hook style headphones for jogging…

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I've had similar issues. Just straight earbuds tend not to work well for me, especially at the gym.
I've been using these: http://www.amazon.com/Philips-Flexible-Headphones-SHS3200-28/dp/B003CJTR82/ref=sr_1_9?ie=UTF8&qid=1338408655&sr=8-9 for a few months now. They tend to stay in fairly well.

I had a pair of these: http://www.amazon.com/Skullcandy-Hanger-Earbuds-HH26-SKC01-Chrome/dp/B0014JFXSK/ that stayed in my ears well but started getting kinda staticy after about six months (used 4-5 days a week, ~90 minutes day, lots of moving around and sweating and sometimes the cord getting yanked on...I'm hard on earphones).

I have a pair of these: http://www.amazon.com/New-Balance-Sport-Earbuds-Adjustable/dp/B007F14724/ref=sr_1_2?ie=UTF8&qid=1338408696&sr=8-2 that I use when mowing the lawn. They're not quite as comfortable and I can't quite figure out why but for shorter periods of time (~30 minutes) they're good.

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I love these: http://www.newegg.com/Product/Product.aspx?Item=N82E16826106424#top

Unfortunately Newegg says they'r eout of stock, so they've likely been superceded by a new model. But there have worked great for me for months. They came with three different size ear cushions and have a hook, soyou should be able to adjust to your preference.

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I have similar problems keeping earbuds from falling out of my ears - I HATE the earbuds that come with Apple products.

I used to have a pair similar, but not exactly the same, as these: http://www.amazon.com/Sennheiser-MX85-Sport-Series-Earbuds/dp/B001GSZAF0 Don't buy these from Amazon though, extremely overpriced, FYI.

Anyway, they have adjustable rubber nubs that help to wedge the earbud in place in your ear bowl(?) outer ear thing(?). The best solution I've found for my freakishly shaped ear canals.

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I have been wearing the slightly older version of these headphones, which I loved: very comfortable on a small ear and did not fall off while working out. The one negative is that I typically needed two hands to put them on because the angles are adjustable; however, it made them more comfortable and fit more closely once they were on. They finally died last week and I've ordered the ones to which I linked as replacements. Hope they work just as well!

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@gt0163c, @elforman, @90mcg112, @neuropsychosocial; Thanks for the suggestions. I will definitely be giving several of these a try. Nice to see that they are reasonably priced too! Have a great day.

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Jimmy, I know I am a little late, but have you looked into Yurbuds? I can't stand normal earbuds, but Yurbuds have performed as advertised and stayed in for hours while working out.

I bought these for biking indoors and running - http://www.amazon.com/Yurbuds-Ironman-Performance-Earphones-Red-10100/dp/B00413XA3G/ref=sr_1_1?ie=UTF8&qid=1338491276&sr=8-1

I bought them when they were only $30. The price seems to fluctuate constantly - http://camelcamelcamel.com/Yurbuds-Ironman-Performance-Earphones-Red-10100/product/B00413XA3G

They also make ones with over the ear clips - http://www.amazon.com/Yurbuds-Ironman-Performance-Earphones-Black-10200/dp/B00503ZT9E/ref=sr_1_4?s=electronics&ie=UTF8&qid=1338491559&sr=1-4

I bought the ones neuro posted at the same time to be my non-working out headphones. They have worked well for me but I would not use them while sweating.

Hope that helps.