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.
DS is 28 months and still loves boobie milk around the clock. I haven't worn maternity bras for at least a year and even in the early days I'd often not be wearing a maternity bra. I found those sports bra type of crop top things wonderful! They don't have underwire, they are supportive and DS can have access whenever he wants without any drama. I have some with wider straps and some with thin straps so they go with any clothing I wear too... I find that I pretty much live in them.
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I go back in normal bras once we're down to 2 feeds per day and it seems to be fine.
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