I wear my hair in a taper cut. Laurelhurst Barber Shop does a nice, professional job of this for $14. I've tried a few of the other cheap haircut places nearby, and none of them did it quite as satisfyingly, although one came close. Being female and wanting a men's hairstyle means confusing lots of people.
This place vacuums your head with a hose afterwards so you don't get little itchy hairs down your shirt, and the barbers are a nice friendly bunch. Be warned, though, they're usually booked up, so call a day in advance.