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1. A transsexual or homosexual (and sometimes heterosexual, though this is a rarer case) female that dresses in men's clothing and dons an air of masculinity.
2. A synonym of drag king.
I nearly mistook that Miss Dandy over there for a man.
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(1) -- A shady male character who has a decieving smile, à le chat Cheshire.
(2) -- A questionable song that sounds charming but at the same time, seems to have darker meaning.
(3a) -- An uber-slick gentleman with a too-enthusiastic smile. Often the gent is hyper-sexual, or enjoys violence.
(3b) -- A Cheshire dandy can also be known by other names, as long as Cheshire accompanies the insult/phrase used.
(4a) -- Old-timey charm mixed with provocative intent.
(4b) -- Cheshire can also be used on its own to speak of a gent.
(1) -- I want to say I believe James' smile, but he seems awfully like a Cheshire dandy.
(2) -- "Where we dwelt by the river, sipping on tea from Long Island, and playing where's the ribbon...? What marvelous times we had, I with my fingers dipped oh-so-sweetly in that cherry pie of yours, dove."
People: "Man, did you hear that song?? What a Cheshire dandy, eh?"
(3) -- "Hey sweetling, want to blow this popsicle stand and head back to my McMansion? I've got a leather collar with your name written ALL over it! Then after, we can watch Boondock Saints. You know how I love watching all the fighting. It gets me so effin' hard. You like it rough, don't you baby?" (insert slimy git grin here!)
Girl: No thank you, damn Cheshire wanker. You're really starting to creep me out.
(4) -- (a couple approaches the stairs)
Guy: You first, sweetling.
Girl: Alright. *starts walking up*
Guy: *behind her* (insert Cheshire grin here!) Damn that ass is hot. Wonder if she'd let me bend her over right here....
Girl: What did you say?!
Guy: I mean, baby, you are the essence of my very soul! Do you know how much I adore you?
Girl: You're such a Cheshire. I KNOW you were checking out my bum.
Guy: *caught red-handed*
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Dandy boys reside in the South Eastern Suburbs of Melbourne City, and were one of the first to put the South East on the map.
Dandenong is full of gangs such as the SC, DB3 and other gangs.
Person one: Ay are you going to that party tonight?
Person two: Nah i herd dandy boys are coming
Person one: Man they always come and f**k shit up
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an elderly gay gentleman with fancy tendencies
My history teacher is such a dandy fop
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Nothing more than another name for a penis.
Sarah: Did you ride Mikes Dandy Train last night?
Katie: You mean his penis?
Sarah: Yes his penis.
Katie: Yeah I rode it all night long.
The act of a post cream pied woman sitting over a man and letting it slowly drip slowly into his belly button.
After a cream pie she gave me the dandy drip
A wholesome shenanigan that’s a dandy ‘ol time.
“That duck rave was a shenanie dandie!”