I prefer shooting headshots outdoors. It feels more natural and relaxed, with natural light and backgrounds (plus a few plain backgrounds courtesy of a reflector that I take to most shoots).
With Fay I went to Church Square Park in Hoboken. It was a warm and sunny December morning (seriously, was there any point in buying that new down jacket?!), with some beautiful light. I wanted to use the sunlight for highlights without creating any harsh shadows, and the little bandstand in the centre of the park was perfect.
ps. I've included a few camera settings to give you an idea of what I'm using. Let me know if they're useful.
pps. Thanks for the tacos Fay!