In the ear vs over the ear will definitely be a personal choice. I love in the ear buds.
For $37 I really like the Skullcandy Method bluetooth earbuds. These have a band that rest around your neck and the buds on a wire that go into your ear. This was the first budget bluetooth headphones I really loved.
Starting at around $65 you can find some LG Tone headsets. Similar neckband designed, but more refined and some with retractable cords. Better quality all around.
If you want to go cheaper than the Skullcandy Method bluetooth buds, there are also really good budget friendly wired Skullcandy options as well starting around $10 or so. And they are available at Best Buy too.
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