Hi Bmc! I apparently have huge ear canals, so I can't recommend a certain brand. But I do recommend the ear buds that have a soft cone (or torus) made to be inserted into the ear, they're way better than the cheap wedge-in type. I go through about one set a year :-o and all the ones I buy come with three different sizes for the "cone", to customize. I think the Koss ones were my favourite, but I think they're discontinued. I had some exercise ones with a curly thingy over the ear, that helped them stay in place.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett