I have absolutely no idea what I'm doing when it comes to buying headphones, but what I do know is that the ones I'm currently using a) look goofy as giggles and b) hurt my ears and c) don't sound that great. So what I'm looking for is a good set of headphones that are comfortable and won't make my ears feel like they're being crushed in a vice and that don't sound completely off. Preferably something under $100 but that gives you a lot to work with from what I gather. I don't care if it has a mic or not as I have a logitech mic that works fine.

I had these RETRO ones that were pretty cheap and sounded good, but the wire broke because a cat chewed on it and now they don't work. I think they sell them at urban outfitters now in lots of different colors. edit: http://www.urbanoutfitters.com/urban/catalog/productdetail.jsp?_dyncharset=ISO-8859-1&navAction=jump&id=15574130&search=true&isProduct=true&parentid=SEARCH+RESULTS&color=10

now I have skullcandy earbuds and they're alright. they've lasted me a long time, don't sound too bad and they look good (black) but now they're popular with "dudebros" or w/e.

http://www.turntablelab.com/dj_equipment/71/144/  Lots of headphones at or under $100.  Companies to check out are Sony and Sennheiser.

Sennheiser 280's and up are pretty good headphones, and I'd recommend Shure 210 or 310's for earphones.

BOSE also makes some pretty decent headphones and earphones and you'll be sure to piss off any 'audiophile' who sees you wearing them which is like a lil' real-life troll.

Bose makes killer headphones, but their low-end stuff is not nearly as good.  I considered getting a couple over-the-ear models they have in the $100-200 pricerange, and while they sounded pretty good and were comfortable, reviews show that they are plagued with reliability issues and the headband and other parts will consistently break.  I would suggest staying away from Bose headphones unless they are the pricey ones.

the on-ear ones are actually pretty sturdy and sound nice(better than the over-ear kind) if you're not bothered by the bassy 'Bose sound' that so many audio nerds pitch a fit about.
I think they're like 30-50 bucks more though.

Koss KSC75

Get these and you will not regret them. I bought these for a friend who needed cheap headphones. I did extensive research and these were the best price:performance I could find. After trying them out before giving them to my friend, I determined that I must have a pair of these.

I also own a pair of Sennheiser HD-595 Premiers... which are audiophile quality headphones. I would say these Koss sound about 3/5 as good for 1/10 the price. Basically you are getting great sounding headphones for a steal.

There are downsides, however. If you are passionately against the ear-clip style, you will not like these. They are not 100% comfortable but they are comfortable enough... and more comfortable than any around the neck headphones.

Another downside is that they feel and even look sort of cheap (up close). But this is fitting as they are cheap.

I really recommend these though despite the cons, as they are virtually the best sounding headphones you will get at that price and even best most headphones that cost 3 times as much.

EDIT: Also I just remembered that a friend had bought a pair of Sennheiser HD-555s and they sounded very similar to my HD-595s (off an iPod - that is, which isn't saying much) but they cost like around $80? They're big though. Very big. Most Sennheiser audiophile headphones are big though.

I tried wearing a pair of earclip ones and I couldn't even get them to fit on my ears (or stay on my ears or really do anything useful at all).  They are p. awful.

Personally, I can't stand almost anything but big over the ear headphones.  I had a pair of Koss ones that got stolen, they were maybe $20 and fantastic for the price.  Now I have some no name brand ones that also work really well, surprisingly enough.  The only other headphones I could ever use are the earbuds that come with ipods, just because I was stuck using them for a while.

I have pretty much used skullcandy in-ear buds for the past year because they were the first pair of noise-canceling headphones I had ever purchased and was amazed at how better music sounds when you can't hear anything else around you!!

The only problem I have with them is that they are extremely sensitive in the sense that having the wire rub against your jacket/shirt/whatever will make annoying low sound waves travel up to your ears.

 I absolutely hate those wrap-around behind-the-neck headphones (oh and those normal ones that just work like a headband (i dont know any technical names)). Every time I've tried a pair, they were always TOO FAR AWAY from my ear to sound good. You end having to use your hands to press them tightly to your ears in order to hear any bass.

I'm surprised so many people here use fairly expensive headphones! I have never owned a pair of headphones that cost more than $25 and am curious to know how greatly the sound quality improves per $$ increase. Apparently those huge padded ear-warmer-esque headphones are the way to go???? Can anyone recommend me a pair for like $50-60, maybe $70 max???

Oh, yeah, I forgot about those.  darkwhite has a pair and he's happy with them.  I've heard their lower-priced earbuds are reliable, but the EARMUFF style ones in that pricerange not so much.  I've never tried the earbuds but it's surprising they'd be bassy!  Most earbuds I use end up being tinny and kinda shitty.  I don't use $200 earbuds, though!

I have a pair of those earbuds at work, they sound decent for their price(like $99) and and the gel canal-shaped earpiece on them is very comfy so my ears don't hurt from wearing them for over an hour.

You're right though, if you want really good sound from earbuds you're gonna need to spend like 200+ for ones on the middle to high end.

I had a PRO GAMER NERD headset which was pretty nice, especially the mic but both arms or whatever broke now so I dug out a little pair of sennheiser headphones i got about 2 years ago and the sound quality is much nicer. I dunno if they're ON EAR or OVER EAR though because searching for both those terms gives headphones that look basically the same to me heh. They can get a little uncomfortable after a long wow stint or whatever but it seems to be mainly because the arm extender things can slip longer over time and it puts pressure on the bottom of my ears. the also fold up cleverly into a lil package which is nice

idk these maybe.  i like sennheiser and they are only $50 and well-reviewed so yeah.  the lack of an ear cavity seems a little odd, but i've worn bose headphones like that that still felt snug/secure and really comfortable and sounded good as well, so i guess it doesn't actually make a difference.

According to this reviewer who owned both a pair of HD-555s and HD-415s, the difference is night and day (the 555s are obviously the better of the two... as they cost more).

HD-555s on Amazon. Right about the price you were looking at.

Again though, I feel I should tell you about the downsides. 6' cord. Pretty big and may look "goofy" if you're self-conscious about this sort of thing (what I'm saying is that they stand out a lot more than - say - iPod earbuds). They leak sound if you have it nice and loud - people WILL hear your music at even moderately high volumes. They aren't noise-cancelling so you can hear people around you. I don't know if those 415s have these issues.

I dunno if they're ON EAR or OVER EAR though because searching for both those terms gives headphones that look basically the same to me heh.

As far as I've always thought, over the ear headphones don't actually touch your ear (it goes around them), whereas on ear headphones are touching your ear and rest directly on them.  I used to have a pair of on ear headphones and they always hurt because I wear glasses, so it was constantly pressing my ears into the sides of my glasses.  Over the ear ones still press on my glasses just a little, but they don't hurt my ears at all.

As far as I've always thought, over the ear headphones don't actually touch your ear (it goes around them), whereas on ear headphones are touching your ear and rest directly on them.  I used to have a pair of on ear headphones and they always hurt because I wear glasses, so it was constantly pressing my ears into the sides of my glasses.  Over the ear ones still press on my glasses just a little, but they don't hurt my ears at all.

Oh man yeah I used to get that when i wore my glasses with my old headset, annoying as hell

I'm pretty satisfied with my Skullcandys. I mean, I've never bought any expensive headphones, and yes, I know they do sound nice, but if I had to vote what sounded the best for the moneys worth, I'd say Skullcandy.

I bought a pair of Sennheiser 477s after headphonics told me about his 480s, and I have to agree, Sennheiser makes good headphones. Granted, I'm not an audiophile, but as someone who has used OFF BRAND $15 headphones all his life, spending 60 bucks for these has opened up a WHOLE NEW WORLD for me.

As for comfort, well, I still find them hot/tight for long, long use, but I've yet to really find headphones that aren't like that. I guess it's just the nature of covering/obstructing the ears. Despite this, I would definitely say they are the MOST comfortable headphones I've ever owned, even if they aren't COMPLETELY comfortable for extended use.