It took me approximately six months to get used to it and stop reflexively covering my breasts when they moved too much (e.g. running or going down stairs) or when talking to people. I am still pretty conscious of them when my nipples poke out, but that rarely happens and I’m starting to care less and less.
I never really noticed how awful bras were until I took a break. After about two months of going braless on a whim, I started to find bras completely intolerable, especially in hot weather. They make me sweat, dig into my shoulders, and hurt my back and ribs. And yes, I’ve tried professionally fitted ones.
Nowadays I never wear bras under anything, and use thin, reusable silicone nipple pads (I like Nippies, but there are plenty of brands; paper medical tape also works well) under see-through shirts or in situations when I feel the need to hide my bralessness (such as job interviews). 20 months ago