Zessica Wong from Aquarion Evol wears a short halterneck crop with a very large opening exposing her cleavage.
The titular heroine's outfit in Cutey Honey is a sleeveless unitard with a huge diamond shaped cutout that even shows off a bit of stomach. In Re: Cutey Honey she wears a halterneck crop top with a heart shaped hole over her cleavage.
Melissa's clerid dress in Rune Soldier Louie has a diamond shaped opening show off her cleavage. Genie's halterneck crop top has two opening, one on top of her cleavage and one on top of her Underboobs.
The Dirty Pair had these in some of their appearances, when the character design included collars that buttoned up but a large diamond shaped opening exposing their cleavages.
Arf's outfit in the first season of Magical Girl Lyrical Nanoha had a crop top with a diamond shaped keyhole. There's also Linith, Fate's Parental Substitute before the series started, who wore an outfit that comprised an outer-coat with buttoned collar and buttoned below her chest and dress with a diamond shaped cutout above her cleavage.
Ran in One Piece wears a crop top with a window hole in the middle.
Yin of the Darker Than Black franchise costume contains a mild version of this. She's far from well-endowed but, the combination of her dress and throw create a patch of visible skin.◊
Fittingly, her Expy, Golden Darkness (Yami) of To Love-Ru also has one, though in a diamond pattern and a single piece of cloth.
Mizuho in Please Teacher! could, in her alien outfit, open up a cleavage cutout by will, and did so in her attempt to seduce Kei.
A great number of Yuuko's costumes in Xxx HO Li C.
Ah! My Goddess Belldandy. Yes, Belldandy. It's the only skin showing in that outfit besides her face.
In the first season of Galaxy Angel, Forte wears a dress with opening showing off most of her chest and Ranpha wears a Chinese inspired dress with a diamond shaped cutout above her cleavage. They were covered up in the second season onward for some reason.
In one instance of Death Note, model/actress Misa Amane attempts to get Matsuda out of a jam with a roomful of shady businessmen by pretending to want to be a model/spokesperson for them. She is seen with a tank top with a heart-shaped cut that revealed her cleavage
Medaka's student council outfit in Medaka Box has a huge opening on the chest area that shows off a lot of cleavage.
Amusingly, it becomes a major plot point because it violates the dress code.
Isabella from Beelzebub has a small opening in the chest area of her maid uniform.
A number of Robes in Mai-Otome cover their wearers from head-to-toe but leave opening to show off cleavage, mainly Maria's, Fiar's, Chie's second Robe, and Mai's. Akane's Robe just has it: only a little bit of fabric keeps it from Impossibly Low Neckline. Oddly, Haruka's (for lack of a better term) off-duty uniform has a diamond shaped cleavage cutout, but not her Robe, as is the case with Una Shamrock in Mai-Otome 0~S.ifr~.
If it's possible for a male character to exhibit this trope, then Giorno and Bruno from JoJo's Bizarre Adventure: Part 5 both have this as part of their outfits. Giorno's is even heart-shaped.
Comics — Books
Many of Power Girl's costumes have openings that exposes her cleavage◊ (one of which is the trope picture). There are a number of issues where Power Girl explains the rationale behind it but the reason seems to change every time. It serves as distraction, it shows that she's proud of her body, and she can't decide on a Chest Insignia.
She eventually gets her iconic, plays-this-trope-straight, costume back after about a year.
One popular fan theory is that the window actually is a sort of Chest Insignia. If you look at it the right way it resembles the symbol on a computer's POWER button, you see.
Phantom Lady in 1946 had one of the first ones with her costume which was a mini dress with a plunging neckline and cape wrapped around her neck. Most of the other costumes merely had an Impossibly Low Neckline.
Invisible Woman of Fantastic Four had one, shaped like the figure 4, in her 1990s outfit. On more than one occasion has it been pointed out the physical improbability of maintaining the appearance of a number 4 in such a manner.
Rocket's first costume is a full bodysuit and a jacket covered her from head-to-toe but the bodysuit had a cleavage cutout, to Icon's vague disapproval. Her second costume, which Icon designed, eschewed this.
Taken to its extreme in Transmetropolitan #24. Channon Yarrow(an ex-stripper) wears a backless, strapless dress with an Impossibly Low Neckline, sides slit to the hips, thigh-to-knee diagonal hemlines(opposing angles front and back), armpit length gloves, and no less than ten triangular windows; three on the outside of each glove, one on each side of her waist, one exposing her bellybutton, and one fully exposing her left nipple. For Bonus Points, she wears the triangle of fabric as a necklace.
Ra's al Ghul's daughter Talia often wears a gown with a cleavage window in the Batman comics.
In The Wheel of Time Ebou Dari dresses are described as having an oval cut out exposing the inner slopes of the wearer's bosom. On married local women, this is to frame the marriage knife, who's hilt nestles between the breasts.
Another claim was that the armor was enchanted and either extended mystic protection to the open area, or that there was armor there that was made invisible.
The entire thing was lampshaded when Alias guest-starred in the Forgotten Realms comic book in 1989, and the halfling Foxilon Cardluck had the following exchange with her:
Foxy: Uhh... Doesn't that armor get drafty sometimes? Alias: It's enchanted. Foxy:(under his breath) Oh, I'll just bet it is.
From Star Trek: The Next Generation onward, the female Klingons are wearing outfits similar to their male counterparts, except with a cleavage-baring opening on the chest armor. Probably has something to do with the whole Space Viking motif. This is particularly silly, considering that Klingons attack each other with bladed weapons all the time. Even considering that Klingons have not one but two hearts.
Captain Liberty of The Tick has a star-shaped cutout on the chest of her leotard.
In season 2 of Babylon 5, Delenn experiments by exchanging her usual robes for a slinky black dress with a diamond-shaped opening over her cleavage. Everyone who sees her is stunned speechless.
Alexia from Pixelface has a bodysuit with a pentagon shaped cleavage cutout.
Music
Nicki Minaj in her "Turn Me On" music video wears a black Victorian style dress with a diamond shaped cleavage cutout.
Hyosung from Korean girl group Secret wore a white mini dress with a large cleavage cutout.
Many of the WWE Divas wear outfits like that, most notably Maryse.
Before she became Molly Holly in WWE, WCW's Mona used to wrestle in a Mini Dress Of Power with a triangle shaped window.
Video Games
With some exceptions, almost every "Harness"-type body armor in Final Fantasy XI will have enclosing chest opening for both females and males. The defensive value of a Cleavage Window is hotly contested.
Fina's dress in Skies Of Arcadia has a triangle shaped cutout in the chest area . It also has the distinction of a purpose outside of fanservice. The exposed skin is where Fina's shard of the Silver Moon Crystal appears.
Hsien-Ko from Darkstalkers wears an overtunic with a large oval shaped chest opening.
Norma in Tales Of Legendia wears mini dress with a diamond shaped cutout at the center. She's also the least-endowed of the Legendia girls.
Leslie's crop top in Arc Rise Fantasia has multiple openings in the center, two of which show off her cleavage and Underboobs.
Sonic Heroes: Rouge wears a bodysuit with an enclosed opening that shows off her cleavage.
Orlha in Chrono Cross has mini dress with large diamond cutout in the center that shows off cleavage and some stomach.
In the first Master Of Orion game, the Mrrshan ambassador has an halterneck outfit with a large keyhole in the front.
In Conduit 2, Andromeda's full-body armor covers everything except her face and the tops of her breasts.
In Okami, the first form/clothing set of Wood Sprite Sakuya, who is a peach tree spirit, has two Cleavage Windows. The first one is a diamond shaped cutout showing off her cleavage. The second ones bares her buttocks, to go even further then the first one in using her figure to remind a viewer of her connection to peaches.
Neptunia has Neptune and Noire in their HDD forms wearing leotards with openings in the chest area.
Cave from mk-2 has a Cleavage Window as well with her Deathsmiles-esque attire.
Bayonetta's default outfit has a large circular boob window. This is also where she wears her umbran watch.
Maya in Borderlands 2 has a small one. It's less noticeable than most on this list, partly because of her proportions and partly because of her default color scheme.
The Vicious Embersilk Robe (and other robes with the same model) all show up as a very modest dress on female characters... minus the large Cleavage Window.
In Tales Of Symphonia, Martel has a triangle shaped cleavage cutout in the flashback scenes, although it's hard to catch. It's a lot more noticeable in The Anime of the Game.
Both Gold Jane and Iron Jane of the Jane Gang from Everyday Heroes wear leotards with teardrop shaped cutouts above their cutout.
Crossroads from Antihero For Hire wore a bodysuit that had as cross shaped cutout in the chest area early appearances. Luckily, she realized how ridiculous that costume looked, so she changed it.
Lampshaded when discussing the design of Spinnerette's new suit, here.
Spinnerette: [...] If you could just give it a lower neckline with some cleavage[...] Sahira: What? Spinnerette: Y'know. To distract the bad guys. Sahira: You have a bullet-proof fabric, and you want to cut a hole in it right over your heart?! Are you insane?
Super MILF used to have one as her previously costume was a rip off of Power Girl. She apparently justifies this in that her "venusian bust" generates so much heat that she requires air venting. At least, that's what she says, though she also openly makes her opinion clear that the majority of costumed vigilantes do what they do mostly for sexual thrills, so...
Ferretina's, the Weasel Queen's outfit from this non-canon Girl Genius comic. She wears a torn crop top that not only shows off her Underboobs but also has a oval shaped cut out above her cleavage.
Crimson, who is at the Superhero School Whateley Academy in the Whateley Universe. She has a diamond shaped window large enough that Phase thinks she's risking a wardrobe malfunction.
Western Animation
Galatea from the DCAU has an oval shaped opening on her white leotard; granted she's supposed to be an Expy of Power Girl.
The Futurama DVD commentaries mention that the animators liked putting Leela and Amy in dresses with these whenever the plot required them to dress up. Lampshaded in one episode that had random time skips during a basketball game. Amy, wearing such an outfit, immediately brings attention to it as a possible explanation.
In "The Devil's Hands are Idle Playthings," Leela wears a long formal dress with a keyhole in the chest to Fry's opera.
Izzy from Total Drama has one in her signature outfit. The top is a crop top with triangle shaped keyhole. In the second aftermath of Action, she uses hers to hold grapes, cheese and crackers, as well as the crumbs she spit out after realizing she was on the green room's TV.
In Stan Lee's Stripperella the title character changes her costume midway through the series. It looks similar to her old costume, the difference being her long sleeved crop top has a huge enclosed diamond shaped cutout.
There are probably plenty of these at model shoots and show business events, but such an outfit can be very — notable anywhere else. In May 2012, a model named Julia Orayén was hired to present some materials to the candidates at the start of a Mexican presidential debate. On camera for less than 30 seconds, her tight dress with a large keyhole was an instant Twitter sensation, and news reports worldwide declared how she had upstaged — or even "won" — the debate.
