Going braless doesn't mean the same thing it did in the 1960s. Many outfits make wearing a bra difficult. Going braless can also be very comfortable. Regardless of your reason, if you decide to go braless, be sure you do it with class.
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Consider your size. Women with smaller chests have an easier time going braless. If you are well-endowed, going braless can actually be painful.
Ask yourself if it's appropriate to be bra free at your destination. Professionalism and going braless do not generally go together. Going braless on the job is usually a bad idea.
Think about your company. Going braless with your girlfriends is different than going braless while meeting your boyfriend and his parents for a formal dinner.
Choose your shirt or top. Going braless in a thin or pale shirt can be in poor taste. Showing too much while wearing too little underneath might give people the wrong impression.
Cover your nipples. No one may notice you are braless, but if your nipples are protruding, you may attract unwanted attention.
Consider support. When you wear a strapless top or fancy dress, going braless may be the only option. Consider purchasing some gel supports to flatter your cleavage.