I honestly prefer big headphones over in-ear headphones. In-ear headphones, or earbuds, just plain hurt my ears. Not because of the volume of the music or anything like that, but because of the shape of the bud. It's really uncomfortable, and I have no idea who thought that it would be a good idea to shape them that way.

it depends for me. If I am playing video games, I need headphones for gaming so I can chat with people, then I prefer headphones that surround my ears. But, if it is just for listening to music on the go, like from an iPod or whatever, then I prefer buds. I never really liked those old ones that had the plastic peace that rested on the top of my head. 

LunarDarkness2 : Then ones they give in airplanes (where the bud is surrounded by a rubber... thing) are usually very comfortable. But I agree that those that simply have a hard part going in your ear get VERY uncomfortable.

As a fair summary...

Over-ear headphones: Comfortable for under an hour's worth of use. Anything over that can easily result in headaches, some severe depending the volume of music for a duration of time. Then again, I guess the comfort of these things also depend on how their made.(Seeing as some headphones' material is as hard as heck when putting over your ear.) It's harder to break though, depending on the brand, so that's a plus.

Earbuds: Very small, usually affordable, all the more easier to break. They are still rather comfortable enough and slip easily into your ear. Sometimes, depending on the form, it slips out just as easily as it does in.Twisting around the middle and bottom part of the cord can be an issue too. This usually leads to the sound-coming-out-of-one-side issue.

In-ear headphones: Can vary on comfort. Also pretty affordable Sometimes they fit perfectly, sometimes not, I find the rubber tipped ones do quite nicely, and sometimes come with extra pairs of different sizes you can swap out. Like earbuds, they suffer the same problem of falling out AND being just as susceptible to damage.

I've always loved over-ear headphones and I find them to be almost constantly comfortable if I have my glasses off when wearing them. Even if I wear them for an hour or more, I usually don't have any issues with how comfortable they are!

However, I can never be comfortable with earbuds in my ears. As if it isn't bad enough that I'm uncomfortable wearing earbuds, I always worry about it when people try sharing their earbuds with me. When we share earbuds, we share earwax. Ew.

I find Sony headphones the most comfortable, but there are also huge Sentry headphones that my mom and I bought for only $20 that I find really comfortable.

I prefer ear buds because regular headphones get uncomfortable due to me needing to wear glasses. Even though sometimes the ear buds fall out of my ears, I prefer them because they're far more comfortable and less bulky.

I prefer over the ear headphones. Surround sound is a plus. Also I need a wireless / wired head set. I have destroyed too many headsets by getting up while they were plugged in. I currently use a Logitech g930. It has surround sound and super comfortable headphone pads. Completely noise canceling and is both wired and wireless. I have never had any issue running it wireless, very rarely cuts out. Takes 3-4 hours to charge and holds an 8 hour charge. I love them. I would recommend them to anyone who is wanting a good pair of headphones. They are not cheap. I work at home so I have to wear them for 8 hours a day. They are never uncomfortable and they do not make me sweat very much. Honestly they are the best headphones I have ever owned. The mic is flawless as well. Also if you are getting your headphones for pc gaming, stay away from Turtle beach. They are not worth the price. Sure if you use them for xbox maybe, but there are a lot better head phones for the pc for the same price. 

Lol Wally... Brag much? Well not only am I at your house, but I am using your headset. muwahahaha. I really do like it, but I don't see why you would pay that much just for the wireless. I mean i feel you could get the same sound quality for like $50 cheaper. Just doesnt seem worth it to pay that much for wireless capabilities. But to each their own. I will try not to break this thing, but then again the sooner you get back here the less likely I am to break it.

Did you even read my post Charlie? Did you have a little case of ADD while reading this thread. I said I keep ripping the cord out of the computer. I also run over the cord a lot, which can cause some damage. I would rather pay the extra $50 for mobility and ease of mind knowing I am not going to destroy it by ripping the cord out or running it over with my chair. I have destroyed 5 headsets so far in the last 8 years. That is a ridiculous amount when each headset was from $40-$80. If I pay the extra $50 or whatever you say it is I won't need to replace these for a long time considering how my headsets usually break. I think everyone who owns a pair of surround sound head phones and wants wireless should get this pair, it isn't bragging. By the way if you break it you buy it, seriously don't break it. I will be very very angry. Should be home in about 40 minutes.

I wear headphones because they're more comfortable and less of a hassle with accidentally pulling them out your ear and hurting yourself like in ear ones.. 

Plus most decent headphones/ headsets have far better sound quality and are way better at drowning out sound.. I mean as someone that respects other people in public transport I don't think they'll appreciate some of the music that I listen to lol.. 

At the moment though I'm just using a z22 turtle beach headset.. Nothing amazingly special but it does have bass and treble lol.. So it's great for drowning out other people aka my housemates

Also personally whilst wireless stuff is great.. It's pretty pointless unless you fail to look after your stuff.

I have 2 pairs that I use regularly right now: I have my Skull Candy earbuds that I don't use as much, and then I have my XBOX ONE headphones that I wear whenever I am playing a game on my XBOX ONE by myself, or I feel like listening to my music on my phone while I am in public. 
The main thing is the comfort-ability of how it feels on the top of my head, as I do have a weirdly shaped head. 

I've always preferred Headphones over Earbuds. While Earbuds may usually be a bit more comfy in my opinion it's not that bad, and they keep falling out of my ears >.> Maybe it's just something about my ears I don't know, but when I have the option I prefer using Headphones.

They also usually have much better sound which is nice.