Reasons you should go braless more often:
Science says it's better for you in terms of perkiness
Bras are ridiculously expensive
Bras are uncomfortable
More clothing is being designed where going braless is the entire point
If you have big boobs, going braless is doable but will take more effort, and of course you won't know if you can go braless if you don't try.
My decision to go braless more often is a comfort thing. I recently got sized, professionally (or rather "professionally" to be accurate) and if you have ever seen the first Pirates of Caribbean movie, you know what I am talking about when I say I feel like Elizabeth at the beginning of the movie whenever I wear any of the bras the sales lady said was my size.
Yes this scene right here.
When I am wearing the bras the sizing lady gave me, I can't even take a full breath, a half breath at most. And I can never wear the bras she gave me for more than a few hours. The sizing lady emphasized wearing bras that fit very, very snug. I know bras are supposed to be snug against your rib cage, but if I can't take a full breath that's a problem. Especially since I can take a full breath when I am wearing a corset. A freaking corset. The sizing lady is probably an idiot and there is a chance I was wearing the right size before she "sized" me. I should've never agreed to getting sized because she threw away the bra I was wearing when I went into the store. That was the only bra I could take a full breath in.
The first step to going braless and feeling confident about it, is to accept your boobs for what they are. Society has warped our ideas of boobs and I am glad that shows like Game of Thrones are setting the record straight for what boobs actually look like. And of course the lack of sex education at least in America does not help. Seriously NO ONE has comic book boobs at least not naturally. I am getting back pain just by looking at this picture.
If people stare at you, stare back. Your nipples might show time to time. It shouldn't be a big shock to people that women have nipples or that some women don't like bras. Just say YOLO and go on your merry, braless way. But if you are worried about your nipples showing, pasties made of silicone, paper, or cloth will help. If you are wearing a more sexy garment, clothing tape will help.
Bralettes are great to wear in place of a bra. While you're not technically 100% braless, you're close. A bralette is a step above going braless but a step below a sports bra. It basically works like this: Bra--sports bra--bralette--braless.
Tank tops with a built in shelf are good to wear if you don't have a bralette (but if you feel up to it, you can sew a bralette yourself) since they are cheap and available at almost all clothing stores.
Form fitting clothing will help. The tighter the clothing is, the less likely your boobs will move.
Plus there are dresses and shirts designed like this where it will look weird if you did wear a bra.
If you want to wear a normal shirt but are worried about your nipples showing, then just wear a scarf or a jean jacket over your shirt. If you have big boobs but want to go braless, wearing layers is helpful. This outfit is definitely doable all you have to wear underneath is a bralette or a tank top with built in shelf.
Of course you can't always go braless, like if you are wearing a white T-shirt, where in this case going braless wouldn't be the best idea.