[lemisanthrope]

I love earbuds.  So small...they take up so little room in my bag that is always stuffed to the max with all the junk I carry around every day.  They attract no attention, leak little noise, and sound good.  But...so damn uncomfortable.  Either have to be worn over ear or with a terribly annoying earhook or be jammed uncomfortably far into my ear canal, lest they fall out with each slight catch on the cord.
The only earbuds I've ever liked were the now unavailable Sennheiser MX-90.  So comfortable, and didn't fall out of my ear.  LOVED them.  But now they've developed a short in the cord to the left bud.  I would love to either find something comfortable, or maybe I should actually send them into Sennheiser and pay $20 to have the short fixed?  In any case, I'd rather not spend more than ~$50 for new earbuds right now.  Though I find earhooks uncomfortable, I find them preferable to the jam-them-all-the-way-up-your-freakin-ear-canal buds.  I've been through ljokerl's multi-IEM review (that guy is amazing...incredible resource for research.  Thanks ljokerl!) as well as several other threads and resources.  But I still feel unsatisfied on information specifically pertaining to comfy IEM's with an earhook or other retention mechanism (like the MX90's) at a good value.
Right now, I'm leaning toward just having my old MX90's repaired, unless somebody presents me with an awesome alternative.  Thanks, y'all!
EDIT: Pic of the MX90's: http://images.productwiki.com/upload/images/sennheiser_mx_90_vc_style-600-600.jpg

 

[SolidVictory]

Have you ever tried Comply foam tips with some of your IEMs? They are the most comfortable tips I used when I had universals. They make a bunch of them for many different IEM manufacturers. You should check them out.

 

[Br777]

i personally find the Klipsch line of IEM's to be the most comfortable.. well i should say the tips.. most other earbud tips just drive me nuts..  also the cheaply priced klipsch x4's dont sound half bad for their price range.
 
alos check this out -
 

***Earbud Guide - 14 Earbuds compared***

 
cheater is a great resource for earbuds.. not to be confused with IEM's... there are several he has reviewed in your price range.. the new blox line comes to mind.
 
 
 
 

 

[Yggdrassilious]

Maybe give us more information on the types of IEMs you've tried, and what didn't you like about their fit and comfort?
 
Some IEMs have angled nozzles and they don't insert very deep at all. That, combined with Comply foam tips, usually is the choice of comfort. Also it depends on the type of deep insertion, and the quality of tips used. I find Etymotics with their small tri-flanges give me the best comfort, even better than Shures with olive tips or Ultimate Ears with Comply. However I hate CK10 and MTPC with Monster tri-flanges.
 
For under $50 though, maybe try something like the Brainwavz Beta, which for $14 actually comes with foam tips, or Brookstone Clear Dual-Drive, and see if you like the hybrid earbud/IEM styled earphones. 

 

[navmau]

Quote:

i personally find the Klipsch line of IEM's to be the most comfortable.. well i should say the tips.. most other earbud tips just drive me nuts..  also the cheaply priced klipsch x4's dont sound half bad for their price range.
 
alos check this out -
 

***Earbud Guide - 14 Earbuds compared***

 
cheater is a great resource for earbuds.. not to be confused with IEM's... there are several he has reviewed in your price range.. the new blox line comes to mind.
 
 
 
 

+1
The Klipsch eargels are the most comfortable tips I have ever used. I have been using them for ~4yrs now on my Atrio's.
 
 

 

[nfinite]

you can try soundmagic pl 30 for comfort...
or maybe superlux hd 381 series (hybrid earbud & IEM design)...
 
I have both of them, and I can say that they really disappear in my ear when I use them and can hear them for hours without problem..