8
Not to be mistaken for a metrosexual who generally spends a lot of time on his appearance. Although a pretty boy may spend time on his appearance he generally was always pretty - soft featured and more feminine in looks rather than having a square face and chiseled features, usually has a round or oval face. Sometimes androgenous in looks.

Pretty boy usually relates to the hair and face as it does in relation to a girl being pretty.
Hey you're such a pretty boy, you're so pretty P R E TT Y!
by i_am_redgirl August 20, 2007
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9
A male, although not necessarily young, who is aware of and enjoys his attractive qualities and grooms himself to maintain such while paying close attention to face, physical health/fitness and apparel.

Most "pretty boys" possess a high level of self-confidence which borderlines cockiness and arrogance as well as a high sense of self-awareness most consider to be vanity.

While they tend to enjoy making people smile, spending time in front of the mirror and complimenting themselves, most do not like to be called "pretty boy" but, instead, well-groomed or well-maintenanced because the term, used as slang, has also been referenced to homosexuality:

pretty = nice looking (female)
boy = young man

pretty + boy = a boy whose looks resemble that of a female (perhaps in a pink polka-dotted dress)

Preferred terms: Well-groomed, handsome, handsome man, handsome male, well-maintained, well-maintenanced guy
LL Cool J is a pretty boy because he cares about his outer appearance, from head to toe and spends plenty of time in the mirror making sure his face and body look good.

He enjoys smiling, making other people smile and he licks his lips so much it looks like he's doing a commercial for Carmex.
by KLUVATL January 24, 2007
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10
A male most likely in teen years who spend an abnormal amount of time on their looks. Thinks that looking good is the most important thing in the world.Known to be ultra- eye candy. They are often told the should be a model of some kind. They have HUGE egos, and thinks they can get any girl they want. Usually extremely popular & a heart throb with the ladies.In most cases are players or juggle several relationships with women at once. These kinds of guys run high in the black race.
Girl: "Omg, have you ever met Travis! He is GEORGEOUS!"
Freind:" I know I seen him!, but you already know his type girl!."
Girl: "I know he's a 100% prettyboy"
by prettyboyknower May 30, 2009
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11
Carson is such a pretty boy!
by LisaC August 11, 2003
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12
a very handsome young adult, usually gets everything handed to him . Doesn't get into fights but would just get up and walk away, he cares about his appearance and what other people may think. Although he may appear gay to some he is a straight heterosexual male.
joe Johnson is consider to be a pretty boy
by queeeenbee August 08, 2014
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13
a boy (usually teens to late twenties) who has feminine physical (and sometimes mental) traits, such as long eyelashes, high cheekbones, etc. they are usually very skinny, clean and well groomed, possessing delicate beauty and features that appeal to both sexes.
girl: ahhh, im in love with that pretty boy!
boy : *jealous* ughhh,, hes probably gay, just forgot about him. date ME !!!
girl : ... weirdo....
boy : maybe i should be pretty too -_-"
by mi_kyoung April 08, 2011
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14
A somewhat new-ish (yet very common) stereotype that developed in the London/Kent/Essex/Hertfordshire area in England, and is now spreading to many other area's of the country.

- All prettyboy clothes are expensive, and are usually from shops such as Topman and River Island.
- Tight, girly-coloured (pink, yellow, etc) t-shirts that are of no readily identifiable brand and usually have some kind of scrawled pattern or design on the front. No more than 2 layers of clothing can be worn at any time, even in the winter.
- Tight, plain, expensive jeans.
- Trainers, usually white and in girly colours.
- Gelled (but more commonly waxed now a days) hair, sometimes with highlights. Grown quite long.
- Socialise only with other prettyboys/girls.
- Never participate in violence, but love gossiping when fights do erupt, and talking about "what they would have done" in an effort to show masculinity to their girl friends.
- Wear moderate amounts of jewellary.
- Do not go out much. Spend as little time on the streets as possible, as they realise they are a vulnerable target for muggings and random violence.
- Prettyboys are usually friendly, but can come across as irritating, and cocky.
- Prettyboys are usually very wealthy, but can come from a range of social backgrounds. Some prettyboys are ex-rudeboys who see the rudeboy culture as immature.
- Most are popular with girls, as prettyboys dress specifically to appeal to women.
- Follow a strict social strucutre religously. They think they "have a place" in their school/college, and know who they can "talk down to" and who to "suck up to."
- Most will claim they listen to a mix of R&B, hiphop and rock, but really just listen to whatever is in the charts at the moment.

Personally I find prettyboys the scum of the earth, due to their narrow-minded lifestyle and a life amibition to go out with the "buffest" girl in their school.

They like to argue that all groups "follow" each other.
This is not true, and is a weak defense.
Some prettyboys actively admit they wear what the most popular people are wearing. Correct, rudeboys, grungers, etc DO have a sense of style that they stick to, but it is nowhere near as single-minded as the prettboy style.
Don't pretend you don't understand what I just said either... its obvious and you know it!
normal man : "we started on some prettyboys at a house party last night. they shit themselves"

person 1 : "what's your friend like?"
person 2 : "he's a prettyboy"
person 1 : "what a loser"

rudeboy : "*kiss teeth* see dem prettyboys over dere blud..set me da shank init, mans gona jack dem up standard"
by EL June 18, 2006
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