1. In the Bedroom
There is nothing sexier and more alluring than gorgeous lingerie with a little mystery. This is the ideal time to show cleavage. But don't reveal your gift until it's time to unwrap the package.
2. With a Second Date Dress
Unfortunately for the past 3 decades, ladies have rarely been taught how to seduce men with the subtle sexiness most of them crave. Less is more in this case, but less can be more in other cases. Whenever you reveal cleavage, there's a fine line between looking sexy, and looking slutty. If you want a 2nd date, show cleavage, but leave enough to the imagination to leave them begging to see more on the 3rd date.
3. Mystery Cleavage: A button down blouse on the 3rd date
Let's say you're getting ready to have cocktails with a guy you like enough to give him a 3rd date. Nothing's wrong with letting a bit of cleavage reveal itself – as if by accident. Stay buttoned up at work, then reveal mystery cleavage later on.
4. Whenever the Garment Calls For It
There's nothing un-sexier than low cut cleavage that's pinned too far up. For example, Diane Von Furstenberg's wrap dresses. Be careful not to pin the cleavage too high, or when in question, wear a camisole. If you're not daring enough to wear cleavage, then don't buy anything that requires cleavage. If the shoe fits wear it!
5. When The Designer Says 'Let The Girls loose!
Some tank tops, dresses and blouses are designed to show cleavage on purpose. On rare occasions they're meant to be worn with a camisole. Most of the time fabrics such as chiffon, organza or open cut lace are sheer, which means they were designed to show your boobage and your bra on purpose, like Kim Kardashian's alluring look above. I love a sexy demi-cut red lace bra peaking out from under a sheer black blouse. Mix up the unexpected.