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1.
The way women have been for the past thousands of years before the invention of the bra, and the way many women still choose to be today. Unfortunately we live in a society made up of controlling assholes who tell us to wear a bra because it is considered "blasphemy" if we don't, but honestly, there are many men walking around outside with no shirt that could also use a bra
Friend: Hang on a second, I have to go put on my bra.
Me: Screw that, I'm going braless!
by KrazyKurves August 04, 2008
 
2.
When a woman choses to wear an outfit without the use of a support brassiere. Going without her bra, bare boobed if you will.
"going out braless tonight"
by MikeyVanMichealson May 31, 2006
 
3.
1)when a woman wants to make guys hory

2)when it is easy to see a womans hard nipples

i love when chicks are braless. their hard nipples turn me on
 
4.
when a woman (usually some hot chick) doesn't wear a bra so some random dude can come up, reach up her shirt (or just take it off), and feel on her boob(s).

"see that chick right there?"

"ya"

"well, she's braless. let's go take off her shirt"
by Gobama! December 31, 2008