It is quite possible to spot this when the guy has a pink product, while the girl has the same one in blue.
Anime, Manga, and Manhwa
Akira and Mizuki from Ai Ore Love Me subvert this. Akira is feminine-looking and the "princess" of his all-boys school, while Mizuki is androgynous and the "prince" at her all-girls school. However, Akira is quite dominant and masculine and Mizuki isn't really all that boyish.
Asuka and Ryo from Otomen, who embody the feminine/masculine hobbies side of this trope.
Jung Suk Ha and Park Bong Bin from Utopia Of Homosexuality are respectively a Butch Lesbian and a Camp Gay who eventually end up together. Yes, a very misleading title.
Shuichi Nitori and Yoshino Takatsuki, the adolescent protagonists in Wandering Son, each prefer things associated with the opposite gender.
If you think of them as their desired sexes, then this is inverted as Pink Girl, Blue Boy ... then slightly inverted again when you notice Takatsuki has pink hoodies. The anime really likes to throw around pink and blue, especially for the Nitori siblings.
In the manga Otome no Iroha, the main siblings' grandmother comes back from the dead and forcibly Gender Bends them because of this. Her feeling was that the odds of a Pink Boy and a Blue Girl successfully marrying, let alone providing great-grandchildren, were so minute she had to take matters into her own hands.
Your And My Secret features a soft-spoken boy, Akira Urehara and loud-mouthed girl Nanako Momoi being Body Switched into one another's bodies. Just about everyone notices how much more masculine Akira and how feminine Nanako has become, and approve.
Chips (masculine-looking female) and Nachos (feminine male) from Magical Nyan Nyan Taruto. They fit this more in their appearances (especially Nachos), although Nachos is definitely the more sensitive and kinder of the two.
Mako-chan and Touma from Minami-Ke. Makoto isn't girly per se, but most of his scenes alongside the tomboy Touma feature him masquerading as a girl. In one episode, he also describes masculine and feminine traits inherited from his mother and father, respectively.
Akira and Mai's little brother Takumi from Mai-HiME.
Ryuji and Taiga from Toradora have aspects of this in personality, but it contrasts with their appearance. Taiga is small ("looks like a doll") but has a brash, loud and angry personality. Ryuji has the Face of a Thug but is generally quiet and enjoys housework (especially cleaning but also cooking).
Revy and Rock from Black Lagoon. Rock isn't exactly girly, but he's the one Non Action Character of either gender to survive and not start killing people. Revy, meanwhile...
Sora and Yukari from Family Compo are a married transsexual couple. Here is what they look like the one time they dress accordingly to their birth gender.
Chrono and Rosette in Chrono Crusade have elements of this. Chrono is implied in both versions to be better with housework (in the manga he's shown in an apron at one point, and in the anime the Elder says he does the cooking and cleaning for him), and is much more meek and gentle (although has an extreme Berserk Button, often putting him into an Unstoppable Rage), while Rosette is loud, brash, swears constantly and was a Lethal Chef as a child. They both have their moments where they act more stereotypically like their genders (Chrono is very protective of Rosette, and Rosette is very fond of pretty dresses), but they still don't fit neatly into gender roles.
Deunan and Briareos from Appleseed could possibly count, except that Briareos is a hulking cyborg four times the size of Deunan. But their relationship follows the trope pretty straight.
Kazuto "Towa" Sakuma and Miya from Sensual Phrase. He's a very girly-looking musician who dresses as a female even off-stage, she is the Bifauxnen who both dates him and pretty much created his androgynous looks.
The calm and serene So Touma and hyperactive tomboy Kana Mizuhara from QED.
Ryunosuke from Urusei Yatsura was unwillingly raised to be the ultimate manly man by her father, and later discovers she's in an arranged marrage with Nagisa, the ghost of a guy raised to be ultra womanly. Though after coming back to life, he turns out to also be insanely strong, despite mostly hiding it behind over the top girly behavior.
From World Destruction, we have mild mannered Kyrie and arrogant Morte. Because the two are so different, Kyrie has the power to convince Morte to stop destroying the world.
A non-romantic example (not counting Aoi's one-sided crush on her) is Misaki and Aoi from Kaichou wa Maid-sama!.
Andre and Oscar from Rose of Versailles. Perhaps not a textbook example, since Andre is not tremendously effeminate. But Andre is the more sensitive and people oriented one, while Oscar is very direct and more goal oriented. Oscar is referred to as the "light", and Andre as the "shadow".
Baka to Test to Shoukanjuu with the identical twins Yuuko (masculine girl) and Hideyoshi (feminine boy) Kinoshita. While Yuuko is typically feminine in traits (such as being good at cooking), her personality fit this trope because of her aggressive, prideful, arrogant, quick-to-anger, and competitive behavior. Hideyoshi on the other hand is calm, helpful, and supportive. Ironically, he is also much more popular than Yuuko, much to her dismay, because of hislooks.
Hayate the Combat Butler has the titular Hayate Ayasaki being quite feminine and being domestic enough to make women around him feel as if their femininity is challenged and has so far attracted at least one guy who was completely straight before (and fell in love when he thought Hayate was a woman only to later decide it didn't matter). He does, however, possess some masculine traits, such as his strength and skill at swords and firearms. Matching him is the pink-haired swordswoman Hinagiku Katsura who is intelligent, highly athletic, and cooler than any guy at school...making her the idol of the school and attracting both guys and girls alike, and possibly the manliest character in the whole series. However, telling her that she can't do something that would be called girly (cooking, housework, etc.) and/or her chest isn't feminine (at least two times) (i.e. she is flat-chested), or just groping it just once would make her rage. However, each is a bit of a blend in traits, with Hayate trying to be more blue to impress her and Hinagiku trying to be more pink to catch his interest.
Sumire and Momo from Kimi Wa Petto. Sumire is an efficient, successful journalist who watches pro wrestling and Sentai anime in her spare time and is a martial arts master on the side, while Momo is a modern dancer who is fairly emotional and doesn't mind taking on the role of Sumire's pet.
Haikara San Ga Tooru has The Lad-ette Benio in two of these. A non-romantic version with her best male friend Ranmaru (a very feminine-looking boy who's a member of a kabuki troupe — who as much is put in the Unlucky Childhood Friend role), and a more romantic one with her arranged boyfriend Shinobu Iijyuin (who, like the aforementioned Andre Grandier, isn't that girly but is still more patient and sensitive than she is.)
Death Note— Misa and Light. While Misa looks very feminine (Idol Singer, Genki Girl, enjoys cooking, and just wants to be Light/Kiras wife) her personality actually fits this trope. Misa deliberately seeks out dangerous situations and is definitely more of a risk-taker while Light is more cautious and of the two of them she is definitely more sexually aggressive. Misa will go to any lengths to protect Light, even withstanding Cold-Blooded Torture, and she would gladly die for him.
Halle (secret service agent and karate champion) and Mello (Badass effeminate mafia lord).
Haruka and Kotake from Himitsu Kirai. She's a boyish Bifauxnen who practices judo and he's a feminine guy who likes cooking and sewing.
Comics
Possibly Redlance and Nightfall from ElfQuest, although the elves don't quite go for the same kind of gender stereotyping that humans do. More to the point, the siblings Suntop and Ember. When trying to get a studio to do an animated version of the comic, Executive Meddling said that you can't have a calm guy and a tomboyish girl, and this is one of the reasons the author quickly abandoned that studio.
Mister Miracle (escape artist and acrobat from New Genesis) and Big Barda (renegade Apokaliptian gladiator) are in many ways a Happily Married version of this.
Yorick and his love interest finally get together near the end of Y: The Last Man. He compares them to the main couple of Moonlighting (a UST-filled detective series starring Bruce Willis and Cybill Sheperd) , but takes great care of specifying SHE is the Bruce Willis equivalent.
Sin City has a non-romantic variation of this in Dwight and Miho. Dwight is a laid-back everyman while Miho is much more violent and dangerous (which is definitely saying something when you take Dwight's own penchant for violent protectiveness into consideration). In fact, Dwight has expressed fear of Miho in the past and worked to ensure that he didn't piss her off.
Betty and Archie, from the main series, Depending on the Writer. When Archie's car breaks down, Betty fixes it. And there is even one comic where they try to enter a team surfing competition, but since Archie is too weak to carry Betty, Betty carries Archie.
Samantha and Bingo from That Wilkin Boy are Expies of Betty and Archie who fit even better. Samantha is physically very strong, while Bingo is a weak musician. This trope may explain why her father never succeeded in breaking them up or getting her to date a manlier man.
Coraline and Wybie. While Wybie's not girly per se, Coraline is definitely the more aggressive of the two.
There was a short film featured on Logo that showed a Gender Flip of a heterosexual wedding. The bride wore a black pantsuit; the groom wore a white tuxedo and veiled top hat, and held the bouquet as his mother walked him down the aisle. He was also kind of short. Even among the wedding-goers, all the men wore different suits while the women were dressed more low-key. The whole thing was brilliant.
In the movie Lover Come Back, Jerry Webster is emotional and intuitive, while Carol Templeton is logical and reserved. This is taken Up to Eleven when Webster pretends to be a chemist to trick her.
Kung Fu Panda has Tigress and Po, who aren't an Official Couple but have plenty of Ship Tease. Tigress is a tough-as-nails warrior who lacks Tertiary Sexual Characteristics, while Po (who is also a skilled fighter, mind you) has a more cheerful and spirited personality and is an excellent cook.
Older Than Steam, even: in 1620 England, in response to a pamphlet entitled Hic Mulier, or The Man-Woman, which discussed the evils of women who dress and act like men, another pamphlet was published, Haec Vir, or The Womanish Man, stating that women would stop acting like men when men stopped acting like women.
Pinky and Rex about a boy whose nickname was Pinky (his favorite color was pink) and Rex, a girl who liked dinosaurs and soccer.
This is a central theme in the Annie M. G. Schmidt story Het Fornuis Moet Weg ("The Stove Has To Go"). It's about a girl who wants to become a carpenter, and a boy who wants to become a stay-at-home dad. They argue about it with grownups who are moving an old stove out of the house. Eventually, one of the grownups gets an idea: the stove can be seen as a symbol for the old times, when a lack of modern household appliances meant that work around the house took all day and gender roles stayed reinforced. Because of modern luxuries, women now actually have time to study and choose their own careers, so there shouldn't be a need anymore for gender roles to stay as they were. The story is considered a children's classic in The Netherlands.
The main couple in Elinor Glyn's Three Weeks have shades of this, at least in terms of gender roles — Paul is boyish but virginal, beautiful and compared to Sleeping Beauty, and the Lady is older, independent, mature, compelling and in charge.
In a very unusual setup for a Romance Novel, Nora Roberts' Tears Of The Moon has as its romantic leads Shawn, a sensitive songwriter and pub cook, and Brenna, a feisty, tomboyish handywoman.
In Jane Eyre, the title character has more moral strength and self-worth than Mr. Rochester. His feminine side comes out in the course of the relationship.
At first sight, King Verence II and Queen Magrat in Discworld are more Feminine Boy, Feminine Girl. But when push comes to shove Magrat has Hidden Depths and can transform into an Action Girl. Verence ... not so much.
In Monstrous Regiment, The Squad is led by the nervous, book-smart Non-Action Guy Lieutenant Blouse, and Polly, the point of view character, is a BifauxnenAction Girl pulling a successful Sweet Polly Oliver. The story actually contains several biologically female characters who are more butch than Lieutenant Blouse.
In the Warhammer 40k Ravenor novels, Patience Kys and Carl Thonius are described this way. Hyper intelligent, scholarly dandy Thonius is frequently referred to as a pussy, frequently by Patience herself, a vicious battle telekine. This might be entirely fair, as the novel mentions that anything short of an Astartes in full battle plate is a pussy compared to Patience Kys.
There are elements of this in the relationship between Vin (a blunt Action Girl assassin) and Elend (a thoughtful, bookish nobleman) in Mistborn. It's not completely straight- Vin does have a girly side and Elend willget dangerous if sufficiently motivated- but the trope can definitely be seen here.
Jaime Lannister and Brienne of Tarth in A Song of Ice and Fire, aesthetically, at least. Jaime is said to be so handsome it spills over into "pretty" territory, while Brienne is known for her unattractiveness and her un-lady-like habits of wearing armor, wielding a sword, and beating the crap out people who piss her off. They form something of an uneasy Battle Couple in A Storm of Swords.
Live-Action TV
The X-Files was designed partly around this trope. Mulder is emotional and intuitive, cries a couple times a season, and tends to lose fistfights or drop his gun at important moments; Scully is logical, scientific, emotionally reserved, and has Improbable Aiming Skills.
Friendship example: Fez and Donna. He and his girlfriend Big Rhonda subvert it, since she's bigger and stronger than he is but is also an awkward Huge Schoolgirl.
Wash and Zoe from Firefly. He's not girly, but less masculine by comparison.
Lee "Apollo" Adama and Kara "Starbuck" Thrace from the rebooted Battlestar Galactica are an interesting example of how to flip a gender dynamic: it's not so much about the way they look and dress as how they behave with each other. Apollo tends to be the softer, more introspective of the two, while Starbuck is louder, brasher, and more of an alpha than he is. Despite this, no one in-universe sees them as less masculine or less feminine for it.
J.D. and Elliot from Scrubs. Elliot seems to have this in most of her relationships. Kelso once commented on she and Keith's relationship:
Kelso: No, no, continue. You were having an argument, but it was like he's the chick and you're the dude!
And before that, she was dating a male nurse named Paul Flowers.
A non-romantic example from the same show would be J.D. and Denise ('Jo'), copied nearly word-for-word:
Denise: It's like you're the chick and I'm the dude.
Doctor Who: Newly married Amy Pond and Rory Williams seem to be this, as Amy is an Action Girl, while Rory is a bit of a Non-Action Guy and a nurse (and while male nurses are common these days, it's still a profession that's predominantly female where he comes from).
The Doctor lampshades it by referring to them as 'the Ponds' after their marriage, instead of 'The Williams'. Rory doesn't seem very bothered by it.
How I Met Your Mother does a lot of this: the men are sentimental, mild-mannered, reserved, romantic, blissfully domestic (Marshall) or kid-crazy (Ted), and are often made fun of for stereotypically feminine traits, while the women are tough, uncouth, uncultured, boisterous, insensitive, commitment-phobic (Robin), or sex-obsessed (Lily), and often engage in hypermasculine actions as comedy. However, Barney takes the aggressively-heterosexual male stereotype and drives it so far over the edge he overshadows everyone else.
However, Barney also gets his nails done and obsesses over clothing, making him feminine. And Lily is a soft-hearted romantic kindergarten teacher/artist, whereas Marshall is a high-powered lawyer. So it's really played all over the place.
In Kamen Rider OOO, Shintaro Gotou is shown to be more compassionate and gentle than his female sidekick/assistant Satonaka, who hates sweets, can wield a gun with the best of them, and fights evil only because she is paid to do so.
A Square One TV sketch, Battle of the Buldge caterors, featured the Drill Seargent, and the moapy Privite Matter.
The Seargent: Privite Matter?
Privite Matter: Turkey and American, Sir.
Nigel and Syndney of Relic Hunter were pretty much a straight inversion of classic adventure stereotypes. She was the action star, impulsive, fearless one and he was always in need of being rescued. Sort of uneven in that she also often got to be the smart one and the people person.
On "Will & Grace" gay Jack and straight boozehound Karen go to a meeting of an organization that promises to "cure" gayness. There they meet a married couple with a stereotypical effeminate man and very masculine woman who praise the organization. After they walk away tipsy Karen asks "Was that two men or two women?"
In Wheatus song BMX Bandits invokes this trope with Nichole Kidman.
Myth and legend
In Classical Mythology, the twins Apollo and Artemis might be considered such, but only by modern standards. Apollo is sometimes thought of as a bishounen. He is the god of, among other things, music and art. He also spends a lot of time with the Muses. To classical Greeks, however, he was all man. Artemis, meanwhile, is a wild Action Girl who spends most of her time hunting in the wilderness with her Amazon Brigade.
Also Athene and Ares. Both Gods of war and victory, but the male Ares is something of a Glass Cannon and a serious Miles Gloriosus while Athene kicks his ass every time they fight, and is a Genius Bruiser to boot.
In Ovid's Metamorposes, Hermaphroditus and Salmacis. [1]
Professional Wrestling
Beth Phoenix and Santino Marella. Santino also got a bit of this when he started dating Tamina as well but that didn't really last long.
Maxine and Derrick Bateman from NXT Redemption.
Radio
In A Prairie Home Companion: Lake Wobegon, where "all the women are strong, all the men are good-looking, and all the children are above average."
By the standards of the time, Romeo and Juliet, based on the notion that Romeo was emotional (a traditionally feminine trait) while Juliet was practical (a traditionally masculine trait).
This applies to some degree to many of the lead couples in Shakespeare's comedies; the woman is typically wittier and more practical.
This idea is played with in Macbeth, with Lady Macbeth being the more aggressive and ambitious of the two. In fact as soon as she finds out about the witches prophecy she immediately begins formulating how to kill Duncan. While Macbeth is torn with internal guilt about his feelings, she's the one that goads him into doing it by questioning his manhood and saying he has no courage. Of course, after the murder their typical gender roles are reinforced, with Macbeth turning into a kill-crazy tyrant and Lady Macbeth so wracked with guilt that she goes insane.
Video Games
Khalid the sensitive guy with Jaheira as the more masculine one in Baldur's Gate.
Tends to show up with Alistair and a female player character in Dragon Age.
From the Witch Hunt DLC of Dragon Age are Finn and Ariane. Finn is a rather foppish mage that despises the outdoors, while Ariane is an experienced Dalish hunter. Just listen to their dialogue [2]
Aveline and Donnec in Dragon Age 2. He is still a capable member of the city guard, but compared to Aveline, pretty much everyone is soft spoken and sensitive.
Meryl and Johnny in Metal Gear Solid 4. When he proposed to her, she declines. Because she wanted to do that and proposes to him half a minute later.
Meryl and her partner Dave in Policenauts also qualify.
Homer and Edy from Valkyria Chronicles qualify, with the former being a meek, pretty little masochist and the latter a Hot BloodedIdiot Herowhocan't sing. Likewise Karl and Lynn. Although they have similar temperaments, Karl is an engineer supporting the troops while Lynn is in the front lines as a shock trooper.
From Phoenix WrightAce Attorney: Ron & Desireé DeLite◊. Ron's an effeminate, shy, lovestruck man who looks way younger than he is. Desireé's a fun loving, motorbike riding, adventurous woman.
Subverted when you learn that Desireé first fell for Ron when he protected her from a mugger.
Fire Emblem: Radiant Dawn includes Rafiel, prince of the heron laguz, a race too emotionally and physically fragile to attack enemies. The woman who saved his life, to whom he is now wholly devoted? Nailah, the wolf Laguz Royal (read: absurdly badass Crutch Character). One of them wears an elaborate robe, sings like an angel, and has ankle-length golden tresses. Guess which?
Seisen no Keifu has Brigid, an assertive sniper raised by pirates and sensitive, submissive horseback archer Midayle as a predestined pair; to a smaller degree she has these dynamics with her other predestined lover, The Archer Jamuka, who is similar to Midayle but more reserved. Another one would be Tiltyu, the TsundereBlack Magician Girl, and her shy childhood friend and local Badass Adorable Azel.
In Rekka no Ken, we have Lad-ette Vaida and gentle, honorable Heath. Kent and Farina are a borderline case; Kent isn't exactly feminine but he's somewhat shy compared to the outgoing, tomboyish Farina.
Your Mileage May Vary, but a Female Shepard and either Thane or Kaidan can come across like this, especially if Shepard is a hardass renegade. Shepard has to be the strongest human in existence, can drink anyone under the table, headbutts krogan like it's nothing, and generally is a stoic character. Thane and Kaidan meanwhile are sensitive and fairly soft-spoken, very moral, and the former waxes philosophical every so often. As a bonus, at the beginning of Mass Effect 2, Shepard will be clad in the black N7 armour, whilst Kaidan is in the pink and white Phoenix armour.
Lost Odyssey. Possibly Seth and the husband who encouraged her to settle down and have a child. Whether or not he was an 'Action Guy' himself, we don't find out.
In Digger, due to the matriarchal nature of hyenas, gender roles are reversed and this arrangement is the norm rather than the exception. One character, a scrawny skin painter, has to compete with every other male in the tribe for the affection of their strongest warrior.
Borderline example in The Order of the Stick. While Haley is not overly masculine, she is much more direct and goal-oriented than the ditzy and sensitive Elan.
Last Res0rt toys with this when it comes to Jigsaw and Slick — Jigsaw's a bit of a tomboy (her main team color is light blue), while Slick's not above dressing in harem wear (and his team's main color is purple). Of course, they're not quite an Official Couple...
The Nostalgia Chick and The Nostalgia Critic. She's a ladette sociopath who fights dirty and gets turned on by weakness. He's a girly, weepy psychopath who likes to be dominated.
Also done in Suburban Knights with Obscurus Lupa/Critic when she's out of character. She pulls Critic around by his tie, will teach him how to be ladylike whether he likes it or not and eventually pulls out a gun against the enemies while he's learned his "bending like a girl" lesson.
"Monster High" Clawd and Clawdeen, this is well played as Clawd is more Sensitive guy then Manly man. Heck, he's even afraid of his own fierce acting, little sister!
It should be noted that this is only by comparison as while sensitive, Clawd is the captain of the Casketball (basketball) team and is largely seen as The Big Guy / Big Man on Campus alongside Deuce. Clawdeen in turn isn't as masculine as she is sharp witted and fiercely protective of her friends, as this comes up when he begins to start dating her best friend Draculaura. In the past and on usual terms neither are seen this way.
The episode where they watch a play based on the series lampshades this by having Aang portrayed by a Genki Girl woman and Toph by a huge Boisterous Bruiser bodybuilder man (and she actually liked the idea).
Speaking of which, Sokka and Suki. Granted, it's not as extreme, but these two are respectively sensitive and tomboyish enough to qualify, though to an understandably lesser degree.
Kim Possible and her sidekick Ron; she's a relentless overachiever who knows "sixteen forms of kung fu", set herself up as an international Teen Superspy and kicks supervillain butt. He rarely fails to back her up and has his badass moments but is an easygoing type widely thought of as a loser, content to chill. Slightly mixed up in that she still fulfils gender roles such as cheerleading, while he eventually becomes a football player, but then again we see their old Halloween costumes - Kim as a cowboy, Ron as a ballerina. Nuff said.
On the villainous side of the fence, tough-as-nails Shego and sensitive and sometimes downright pouty Dr. Drakken.
Leela and Fry in Futurama have numerous gags invoking this trope, similar to the Kim Possible example above. Kif and Amy also have a relationship with frequently reversed gender roles for the sake of humor, including one episode where Kif got pregnant and Amy abandoned him, afraid of being tied down, only to return just in time to save the day.
On Daria, Helen and Jake have a lot of this—she's a workaholic career women, while he works a lot less and seems to enjoy cooking.
Phil and Lil's parents (Betty and Howard) in Rugrats.
Kimi and her brother Chuckie. Lil plays this with Chuckie, especially with her implied crush on him later on, but in the latter show she's grown up and changed (though she's still tomboyish).
Polish pianist, composer and Ill Boy Frederic Chopin was paired up with George Sand (the nom de plume of Amantine Dupin), a Tom Boy writer overlapped with The Lad-ette.
This is how many saw Michael Jackson and Lisa Marie Presley.
Another sensitive male musician with a harder-edged lady: Kurt Cobain and Courtney Love.
There are several animals that exist where the females are dominant over the males, such as hyenas and spiders.
