A lipstick lesbian is a lesbian who dresses and acts in a manner that is considered conventionally feminine (for instance, wearing lipstick). Main-character lesbians on TV tend to fall into this category more often, as it's often seen as "safer", unless the show is going for "edgy". They also often have things like long fingernails, unlike their more masculine counterpart.
A related term is "femme". However, the implication is that, while a "femme" would be attracted to a "butch", lipstick lesbians are attracted to others of the same type. Also note that in LGBT communities, lipstick lesbians tend to be described as 'more feminine' than average straight women or whose expression of femininity is 'over-the-top'. Ellen De Generes jokingly coined the term "chapstick lesbian" to describe those who fall somewhere in between the two extremes of "lipstick" and "butch".
The real life proportion of lesbians that are lipstick lesbians is somewhat lower than what one might expect from watching television. The reasons for this proportional over-representation can include Fanservice (because Girl on Girl Is Hot), wanting to avert the stereotype of Butch Lesbian (and the Unfortunate Implications that non-heterosexuals are "genderinverted"), wanting to present a lesbian character that won't "intimidate" viewers, and also wanting to avoid making said lesbian character's sexuality an excessively large issue by presenting her as a person who just happens to be attracted to other women.
Related to the opposite of Butch Lesbian, a high femme. Related to, and their frequent representation is perhaps a direct result of, Girl on Girl Is Hot. See Schoolgirl Lesbians, another form of catering to Yuri Fanboys via character type. Lipstick lesbians who don't take the "girliness" to extremes can be seen as Distaff Counterpart to the male Straight Gay, while ones who do, depending on your perspective, can either be seen as counterparts to the Manly Gay (in terms of over-emphasizing the "expected" characteristics of their sex) or the Camp Gay (in terms of going whole-hog into "femininity").
Examples
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Anime & Manga
Michiru Kaioh from Sailor Moon; however, with her girlfriend being the more masculine Haruka, some might say it would be more accurate to describe her as 'femme'. Naturally, most international dubs attemptedto censor this aspect of her character.
Possibly Minto of Tokyo Mew Mew, but when she says she loves Zakuro it could mean either romantic love or just the obsessive admiration for the celebrity and Onee-sama, and she's clearly into boys too.
On the other hand, there's no other explanation for Corina from the English dub, and unlike Minto, she shows no interest in boys at all.
Lavinia from Soukou No Strain. Bunny suit, anyone? And let's not get started on episode seven.
Akko and Mari from Girl Friends. Particularly prevalent since much of the plot includes shopping for clothes, getting makeovers, and hairstyling.
Hazuki from Yami to Boushi to Hon no Tabibito, who has long billowy black hair, a pretty seifuku, stunning blue eyes, and is just slightly gayer than an entire pride parade reenacting the Rocky Horror Picture Show. The object of her affections is even more feminine, though bi- or pan-sexual.
Yamato from Loveless acts as the more "femme" of the female Zeroes, as opposed to her fighter Koya.
To the Pokemon fandom, Candice in the anime, and games to a degree, comes off as this.
Iono the Fanatics is overflowing, with Iono-sama leading the pack/harem. Actually, almost every female ever drawn by Miyabi Fujieda fits in here.
Nobara Yukinokouji from Inu X Boku SS is an attractive woman who works as a bodyguard, and tells Ririchiyo that she would love to be in a sexual relationship with her. She also demonstrates her more feminine aspects by helping Ririchiyo with her hair in episode 3.
DC Comics's current Batwoman is a Lipstick Lesbian. She was 'outed' in a cunningly-written magazine interview several months before the character premiered, and her first comic appearance was in a stunning party dress that caused jaws to drop both in and out of the comic.
Her portrayal changed somewhat between 52 and her stint in Detective Comics. In the latter, she was established as having been in the army and wearing a wig in costume to hide her short hair.
Sydney Krukowski from Dykes To Watch Out For refers to herself as femme, although the way she looks and acts isn't that different from her girlfriend Mo (who is sometimes considered butch.)
Victoria Hand
Karma
Moondragon
Phyla-Vell
Kato in Dynamite Entertainment's modern-day The Green Hornet book.
In the Bluntman and Chronic comics, based on the Comic Book Within A Show of the same name from the View Askewniverse movies, one of their nemeses is a lesbian called the Lipstick Lesbian.
Gianna of Luminosity is this to the extent that no one notices until a female vampire mate-bonds to her. This was intentional on her part, though she doesn't change at all when she gets in an open relationship.
For Yoruichi and Soi Fon fan-fics, Yoruichi is usually portrayed as this out of the pair, at least in terms of aesthetics. In terms of personality, Soi Fon tends to be the submissive partner.
Film
Judy Squires in Better Than Chocolate, who is also a transwoman. Frances, the woman she's in love with, is more of a "chapstick lesbian". Maggie, the main character, is pretty femme-y as well.
Improbably, as is pointed out by some of the characters - including herself, Jacyl from Black Dogs. As an elven scout she's often weeks or months on end in the wilderness with no hot baths and limited pack space, yet she needs to carry several different outfits and makeup along with her. Her former guardian remarked that he first came across her while her house was burning down and that despite this, she was attempting to save her dresses. Her partner is the Butch Lesbian, Sinai.
Felicity Worthington, from the Gemma Doyle Trilogy, behaves like an proper Victorian girl. There are very few hints about her true sexual orientation (subtext only). However, it is revealed in The Sweet Far Thing that she is in fact a lesbian and was in love with Pippa Cross. Probably due to the attitude of the time, she views this part of her with contempt and is in the closet about it; she seems to think that this means there is something wrong with her. Pippa may be another example, although she also expresses interest in boys, so she's probably closer to Bi the Way or If It's You, It's Okay.
In the novelization of Baldur's Gate, it was revealed that Imoen is one.
In Odd Girl Out, published in 1957, the feminine Laura initially doesn't believe she can be a lesbian because she knows about homosexuals—"the men were great sissies, and the womenwore pants."
Several in Mary Renault's work: Valentine in Purposes of Love, Helen in The Friendly Young Ladies, Lasthenia in The Mask of Apollo. Valentine, though, is bisexual, or basically straight but going through a phase. Helen, on the other hand, is more certain of her lesbianism than is her butch lover, Leo.
Katherine Kopeck and Sam Saturn in Adam Christopher's Empire State.
Edie Bannister is a chapstick version in Nick Harkaway's Angelmaker.
The Firefly episode "War Stories" has Inara taking a female client (also of the Lipstick variety). According to Kaylee, this isn't the first time.
Tipping The Velvet had Kitty (when she wasn't dressed as a man for her Music Hall act), Mrs. Lethaby, Florence and Zena. The protagonist Nan starts off as a lipstick lesbian but becomes increasingly butch as the story continues.
Zoe Tate and most of her girlfriends from Emmerdale.
Helena Cain from Battlestar Galactica is on the far "chapstick" end of this (considering that she's a Goddamn admiral, and a hardassed one at that, she's naturally adopted some distinctly masculine mannerisms).
Helena Cain doesn't have masculine characteristics, she's a strict and harsh person. This happens - Marilla from Anne of Green Gables. Also, she's not really shown before the Cylons attacked, so we don't know - maybe she was like this at 18, rather than picking it up from military culture.
Many characters in The L Word, which makes the occasional guest spots by real-life celebrity lesbians all the more jarring: they never look as Hollywood-feminine as the main characters.
Guinevere Turner as Gaby Deveaux, Clementine Ford as Molly Kroll and Leisha Hailey as Alice Pieczecki are all as Hollywood-feminine as any of the straight or bisexual actresses on the show.
DC Jo Masters from The Bill has been described like this, although she doesn't really advertise it. Rather large in the chest department, she had Eddie (the male crime scene examiner) ask her on a date. She told him they'd go for a drink and she'd explain.
Also Gemma Osbourne and lesbian call girl she had an affair with (played by Stacey from Hustle.
Out Of Practice, a failed show on CBS, had a central character who screamed this trope to the heavens. She dressed provocatively, threw herself at women, and couldn't open her mouth without bringing up the topic of her sexuality.
After her coming-out storyline, Beth Jordache from Brookside (played by Anna Friel) was labeled as a "lipstick lesbian" by the British media, receiving equal attention from young women and young men.
She seems to be more of a case of Bi the Way—she still seems to enjoy sex with her husband Jimmy and has had presumably had threesomes with Mary and her husband. When asked if she was in love with Mary, she just replies "I was lonely."
Anne on Go On lost her partner, which is why she's in the support group.
ER's Kerry Weaver is more of a chapstick lesbian—attractive, feminine, but short-haired and abrasive—but her companions tend to fit this trope. (With the slight exception of Sandy, who despite her decidely feminine looks, has a unisex name, is a firefighter, and like Kerry, an abrasive personality).
A surgeon who is the POI of the week and her wife both qualify for this trope in an episode of Person of Interest
Possibly Waitress Aurora in Pokemon Black And White, a character you go onto Ferris Wheel dates with if you play as Hilda. Her Japanese conversation mentions a boy, but the English version excludes that.
More recently, main character Penny is a Lipstick Bisexual, while the other main character (and her girlfriend) Aggie is a lesbian but too much of a hipster to really count as 'Lipstick'.
Kanaya from Homestuck, the troll's "bugging and fussing and meddling" Team Mom, is a lesbian and the only troll with an interest in fashion. Literally a Lipstick Lesbian in that her main weapon is a lipstick that sometimes transforms into a chainsaw.
Girly lesbians are the dominant type in Girls With Slingshots. All of the major lesbian or bisexual characters are prone to curves, makeup, and girly interests. Butch lesbians exist, but they have their own hangouts (one of which Jamie visits during her Coming Out Story arc).
In Shiniez Lisa and Ally become these and Valerie is revealed to be this.
Web Originals
Decades Of Darkness has Julia Gordon. And First Lady Anna Mitchell, which causes a scandal in Columbia (the US capital) and prevents her husband from reelected for a third term.
Aster from Anyone But Me. Vivian is either this or a chapstick lesbian, depending on your perspective
Whateley Universe: Bugs (Bunny Cormick) is regarded as one of the hottest girls at a Superhero School, but is strictly lesbian. She's not the only such girl in Poe Cottage.
Linda Memari of American Dad is possibly bisexual, but she seems to be far more interested in her neighbor Francine than in her husband.
In one episode of "Family Guy", Meg poses as a Lesbian to make friends and gets involved with a girl named Sarah.
Discussed on an episode of King of the Hill, where a subplot involved Hank's driver's license now saying he was a woman. Peggy's hairdresser commented that if they were a lesbian couple, Peggy would be a lipstick lesbian, which is "the best kind".
Real Life
Portia De Rossi. Meanwhile, as noted, her wife Ellen DeGeneres has jokingly referred to herself as a "chapstick lesbian".
Ruby Rose and her (ex-)girlfriend supermodel Catherine McNeil.
Beth Clayton (Opera Singer).
Miss Cleo
Slovak supermodel Yaya Kosikova
Jane Hill (English newsreader)
Lana Turner's daughter Cheryl Crane
Amanda Barrett from the Ditty Bops.
Sophie Ward
Katharine Cornell
Sandi Toksvig
Warhol prodigy Mary Woronov.
Adult actresses Tracey Adams and Julia Parton.
Most of the lesbians on A Shot at Love with Tila Tequila and A Shot at Love with the Ikki Twins.
Ebony Haith, Lulu Braithwaite, Kim Stolz and former Hooters waitress Kayla Farell from Americas Next Top Model and Nanna Grundfeldt winner of Finland's Next Top Model.
Kelly McGillis and Chris Connor as young women (though by the time they publicly acknowledged their lesbianism their appearance had become much more androgynous)
Tammy Bruce
Most of the women featured on The Real L Word particularly Tracey Ryland and Nikki Weiss.
Supermodel Gia Carangi, writer Ariel Levy and musicians Francesca Gregorini and Jill Jackson have aspects of the lipstick lesbian about them as they have long hair and are conventionally attractive but they are a little too tomboyish to completely qualify.
Truth in Television: Leisha Hailey and Alexandra Hedison, who play lipstick lesbians Alice and Dylan on The L Word, are both femme lesbians whose famous dates are more often chapstick lesbians than butch.
