Part ear-bud, part canalphone, the Sennheiser CX300 are my favourite headphones for city life. They fit like a pinky fingertip in your ear and it’s that light seal that affords for very deep bass. They also block most outside noise which is great because they’re great even on the subway, but be careful crossing the street, and for heaven’s sake don’t wear them when you’re riding a bike.
Something strange is happening to their pricing from various merchants Tiger Direct has sold them for as low as $62 but they’re currently listed at $107. A lot of people think that $100 is a lot of money for what are essentially ear buds, but if you are using them every day you will appreciate the difference.