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Depends on whether or not you're hot. If you're hot, you can show as much as you please. If you are ugly as a mud outhouse, consider wearing a turtleneck.
I find it really funny, but I tend to keep my cleavage under wraps, particularly at work. I wear higher cut stuff probably because my mom was so paranoid.
Anyway I seem to get loads of compliments on the days I am showing some cleavage. Men and women. Really funny.
Showing cleavage is entirely inappropriate at work. When wearing evening wear, it's very appropriate and beautiful. It would depend on what type of date I was on if I was going to show any or not.
We sound similar in size and body type. I personally have never worn anything to show more then just minimal cleveage. I see many showing off much more, that's fine for them but I personally just don't think it's all that attractive - in the right way. Very few in my opinion actually look good and the rest look more disheveled and tacky. Again, what others do is up to them but to me personally I don't think excessive cleveage is a good look nor can attract good attention. I would only dress, like others mentioned, how you feel comfortable and not force yourself to show more then you would because you want to look more "sexy". Believe me, looking sexy doesn't mean just showing off skin. I think showing skin can be fine, just done the right way.
I think, if you decide to put cleavage on a 1-10 scale. 1 = no cleavage and 10 = any point below the peak of your breasts, where it transitions from the top to underneath.
At work or church no more than 2-3 on this scale unless your job is at Hooters. 10 and beyond is reserved for at home in private. Or at a Las Vegas night club. 5-6 probably works for date night and most ocassions when you are deciding it is a cleavage day.
I am old fashioned and think that you should only "show" on "sexy" body part at a time. So you shouldn't go backless and have lots of cleavage showing. Or have a super short skirt/dress/shorts and cleavage. Pick one at a time if you are going out.
With the exception of work, church & parent-teacher conferences (I was going to say court but then realized I'd be lying) I draw the (neck)line at the areola. Breasts are pretty.
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