I’ll second the jaybirds! I had a pair of beats and let my wife use my discount to get some jaybirds. I instantly regretted that and wished I would have gotten a pair. I eventually ended up with some jaybird and never looked back. Comfort was the key thing for me and the sound is amazing.
I bought a pair of Skullcandy Hesh headphones 3 years ago (earbuds hurt my ears when weightlifting/fall out when running) for $60. I've ran in the rain, thrown them around, etc., and still going strong, holding 10-12 hours on a charge. I've never had bose or $500 beats, so I guess I don't know what I'm missing either as far as sound quality, but I've been content.
I used to be a bit of a headphone freak, i use Grado SR325's at home. But for working out and cycling I have a cheapo pair of iFogz from best buy. They last all day long and I like the little magnet clip. I can roll the cords around and stow it in my pocket or clip it to my collar.
I will only ever buy Powerbeats from Beats for the gym. I have never found a better option after lifting for 7 years. Heed a warning that anything without the retainer piece that slips behind your ear can come out pretty easy if you ever pinch the wire on something while moving around. I like mine to stay put.
Got my son Beats X, they lasted about a year, sent them back, they give us a new pair for 1/2 price. Not impressed. My boss gave me a pair of Klipsch almost two years ago, no problems, battery life is @12 hours, they sound awesome, better than Beats. They are pretty pricey, even more than beats but well worth it IMO. I've also had several other brands that didn't last long LG, JBL, Sony, a lot of the cheap ones only last a few weeks. I'm only talking about the earbud type. I hear several of the ear muff style are great.
I use the Plantronic's backbeat. Last about 6 hours, They used to be around $100 or so dollars when I first bought them, now you can find them for about $50 or so. They sound good and stays put. Has all the features as well as phone.
I use Skullcandy Method. GET THEM AT BESTBUY WITH THE REPLACEMENT/INSURANCE POLICY! I have gone through 5 pairs in 2.5 years BUT I just swing by Bestbuy and pick up new ones. AND they keep extending the warranty with the new pair. I am not saying these are the greatest earbuds out there but sweat and electronics don't mix well and replacing bose/jaybirds/gucci etc gets expensive quick. ($50 Headphones + $15 Replacement Program) / Time = Cheap Tunes