I have come to the following conclusion: while my head and ear canals are not particularly small, they are most definitely smaller than those found on your average male. This is why most headphones are too big - they're designed for the average male.
Don't get the $10 Rocket Fish/JVC headphones (the audio quality is horrible) and don't get the $40+ Sony/Bose headphones (the audio quality is great but they fall apart after daily use). I stick with headphones in the $20 - $30 range (but don't Skullcandy, you can hear the earbuds moving around in your ear canals).
I don't need perfect audio quality but I don't want to have to turn my iPod up to the max the hear my music with cheap headphones. And I don't want to feel the heartbreak that comes with a pair of expensive headphones falling apart (trust me, it sucks...I ended up trying to tape back together my $50 Phillips clip-on headphones).
I've tried almost every headphone out there and these two work for me:
- Sony Sports Street-Style Headphones: I used to buy them from Best Buy but I haven't been able to find them there, so I just bought a pair online. These headphones are water resistant, so they work great for your workouts when you....glow (because women don't perspire/sweat, we glow). Since they're bulky, I only use them when I'm exercising.
- Sony Earbud EX-Style Headphones: These earbuds are fantastic for the price! Make sure you try on all 3 earbud sizes to find the right fit (it makes a huge difference). These earbuds are my daily headphones...great for commuting, traveling, etc. The sound quality is good (not great) and they don't take up much room in my purse.