Honestly, I only stopped wearing normal bras for the initial couple of weeks with my first while supply settled and since then have worn whatever suits my fancy, underwire and all. I have never had a blocked duct and fed my first for over 3yrs part of which was tandem feeding with my second who is almost 12months now (so almost 4yrs all up without a break). Even if I've gone out and had longer than usual between feeds it has not been an issue.

I'd just try it out if you think you can, obviously it varies greatly from woman to woman.