The JVC Marshmallow headphones are the cheapest offering for small-eared users, averaging well below $20 for the various color options. The small earpieces and compressible foam tips should allow for a fairly comfortable fit, though the short, wide aperture may cause issues for some.
The Radius Atomic Bass earphones have compact earpieces, but the main draw is the longer, angled aperture arm that allows the 'buds to be positioned outside of the ear if necessary. They come with the standard silicone earpieces, but the smallest one is quite tiny.
The Klipsch Image S4's slender, angled aperture arm and tapered earpieces combine with contoured silicone tips to offer an exceptional fit that stays put in the ear. Be sure to clean the sleeves every so often with water and mild soap, though.
The earpieces of the Thinksound Thunder headphones are impressively small, but what's really great is the array of eartips. Thinksound labels them as S, M, L, and XL, but the actual sizing is more like XXS, XS, S, and L. Plus, you can feel good about your purchase since all the materials making up the earphones are repurposed and fully recyclable.
The Audeo Perfect Fit Earphones gain attention for the unique design of the earpieces, which are rather flat and angular rather than bulbous. There's also a pair of compressible foam tips, which tend to work best for those with tiny ears.
The Klipsch Image X10 headphones also feature a unique design in that the earpieces are long and slender rather than squat and bulbous. This allows for a slim diameter at the aperture. Pair this with Klipsch's contoured tips and you have a winning combo for small-eared listeners.