I wear heels all the time. Short ones (3.5") for all day comfort, and taller ones for partying. Many heels look nice, but either are uncomfortable, or have a weird weight thrust which leaves you off balance. My two favorite pairs of shoes are Calvin Klein Ellison wedges and Calvin Klein Louhana sandals. I suggest you buy some cheap heels at GoodWill and experiment until you find a brand and style that are comfortable and easy to walk in.
I've had good luck buying shoes at Goodwill, Payless, Ross, and Amazon. They make high heels for men too, They call them cowboy boots.
Basically, female shoe size = male shoe size+2.