Should A Boy Wear A Skirt?

AdventureDad | January 7

skirt - circle 1.jpgSince I’ve been on paternity leave for 6 months I’ve gotten to know lots of new hot mothers people and their kids. One of my son’s best friends, a fun and lively 4-year old boy, has a somewhat odd habit. I think it’s cool and different while my wife thinks it’s strange and doesn’t want our son to develop this habit. Very unusual since I’m usually the boring one and her the one embracing new and crazy things.

Our little friend loves to wear skirts. His mom is totally fine with this, she bought a few and lets him wear it to school sometimes. His favorite skirt is a yellow one by Pippi Långstrump, or Pippi Longstocking as she’s known in the English speaking world. It’s actually a whole outfit, complete with a pink umbrella. It looks really cute. What about a boy wearing a skirt? Alright with you or totally unthinkable? Perhaps fine alone in the house but not around other people? Is it a good or bad idea to break down some of the clothing stereotypes?

My wife’s Mexican roots certainly has something to do with her being so hesitant about this. Latin men don’t wear skirts or even pink shirts, they are supposed to be macho and cool. She says it just feels wrong to her. I’m not thrilled about it but wouldn’t oppose it. If my son feels strongly about a skirt every now and then, he can wear one.

What do you say, would you send your little boy to day-care in a skirt if he really wanted to?

22 beefs about Should A Boy Wear A Skirt?

  1. Now this is interesting. I’ve bought my son a baby doll and I’d get him a dollhouse and a play kitchen in a heartbeat if it was affordable and I had room, but a skirt… I think I’d want it to be a “kilt” instead.

    I think boys wearing certain clothes and girls wearing certain clothes is ok. I think dressing up as a girl for halloween would be ok too. Or talking about how fashions for men and women change (used to be that men wore wigs and makeup, men wore ‘dresses’ back a long time ago, etc.) but for going out in public I’d encourage at least gender neutral clothing.

    Now if he’s a teenager and doing it, well I might actually be more ok with that. Strange huh. But then it would be his choice with full knowledge of the stares, comments, etc. that he’d be likely to get.

    Very interesting topic though. I’d like to hear more comments.


  2. My initial reaction was ‘no’, but I had to think about why. There are certain modes of dress, such as sexy clothing on small girls, or makeup on small girls, that provoke strong reactions in those who see them and for that reason, parents often prohibit those modes of dress (even though the children enjoy the sparkly, fluffy, colorful clothing and makeup). Haven’t run into anyone whose son wanted to wear skirts, but I sense it would fall into the same category. Like Angela, I would allow a teenager to experiment with rebellious, gender-bending clothing knowing that’s part of the growing-up process…but with a four-year-old, I’d feel compelled to put the brakes on.

    (In the interest of full disclosure…my 2 y.o. son does own a kilt. Given to him by his uncle who has a matching kilt.)


  3. Let him wear the skirt, totally. Prohibition at that age would just cause problems, I suspect.


  4. I only have daughters so I’m having trouble being sure I can answer this honestly. I want to be the parent who would let him wear a skirt. I don’t see any reason to hold him back from that. I’ve been struck a lot by the fact that we tell girls they can do anything, but there are many things we don’t want boys to do because it’s too girly. It seems sad. Both genders should have the freedom to wear any age-appropriate items of clothing.


  5. As a matter of principle, I’d say let him wear the skirt but then I wonder why we women have to keep my tops covered while the guys run around shirtless and comfortable. And the last time I wore a dress was to a funeral. I own one dress and one all purpose skirt.

    However, reality may be a little different. He’s very young and I’m not sure he’d be ready to deal with the cruelty that may ensue at the day care.

    I’d probably try to work out a compromise with him first. Dress up at home; wear “boy” clothes to school.

    If there are serious transgender issues (I don’t know), they’ll surface eventually and it will be a whole new ballgame. Right now it sounds like my youngest who loved to wear girl clothes and play with hair and makeup. He’s outgrown it except for parties.


  6. I probably wouldn’t dress him in the skirt and send him to school, and I know that’s just my own biases kicking in and nothing more. However, I wouldn’t care if he dressed up in play clothes at home or at school and wore a skirt to try on a different role. I used to dress my little brother up in my skirts and play jewelry at home when we played house, and he turned out fine (though my mother surely wondered if she’d made a mistake when my brother favored dressing as a woman for a couple Halloween evenings in a row when he was older).


  7. Oh, I do agree that wearing the skirt at home or playing “dress-up” is totally fine. But I’m just being honest in saying I would prevent the skirt from being worn to school, grocery store, etc.

    In some way, perhaps it’s similar to the scenario in our house where my son wants to keep his pajamas on all day. I’ll let him wear them until we have to go out (or until some point in the afternoon when I decide “it’s time to get dressed”). It’s somewhat arbitrary…the pajamas provide coverage and warmth, and some pajamas aren’t all that different from regular clothes. But something in me won’t allow pajamas to be worn to school!


  8. For me it wouldn’t be so much the fact that my son would be wearing a skirt, it would be the fact that the other kids at daycare (and very possibly their parents) would ridicule him. I see nothing wrong with him wearing it but parental instincts would force me to want to protect him from the “cruel cruel world”.


  9. I am a father of two young daughters, so I too am not sure what I would do. My initial thought is no. Across the street there is a seven year old boy that loves to play dress up all the time. It’s not unusual for him to show up at our front door dressed as a princess. He will wear a skirt all weekend. I know this drives his dad crazy. I have seen other kids make fun of him in the neighborhood. Obviously it’s the parents decision to send their son to school dressed in a dress. The concern I have would be that his schoolmates would make his school life miserable.


  10. Man, I don’t know if I could let my son wear a skirt. I imagine it would be kind of emasculating to him and ruin my plans for him to fight in the UFC.


  11. Not even a question…no way would I let my son do this. I cringe when one of them tries on mom’s high heels, so there’s no way I’d let him do the skirt thing.

    Funny thing is, I’m pretty sure my wife would balk at that too. Even in this “whatever feels good” society, there are boundaries. Boys are boys and girls are girls. Society is going to screw with their gender identity enough when they get older.


  12. Why can´t boys wear skirts - yes, that´s a delicate issue today when more and more boys want longish hair and are not too concerned with looking a little bit more girly! I can´t see no reason why they couldn´t use that nice and comfy garment! (they used to before in the old days without any concern from society)Especially, when you consider that girls wear, what originally were boys´clothes, namely trousers!
    Actually, my neighbour´s son wears skirts all the time and also have long, blond hair! I must say I´m amazed that he dares! According to what I´ve heard from my own son, he was teased in the beginning but he just stayed cool and suffered it through! When the other pupils noticed that he was unaffected, they stopped and it even made the girls getting very positive toward him! They always love to dress this boy up in girls´ clothes, whenever they´re allowed! And they sort of love it!
    Yes, it´s strange, sometimes you get those very daring boys (and girls) who go their own way in life and this boy must certainly be one of them!
    I was very negative in the beginning when I found out that he really was a boy, but I´ve thought it through and if I let my feelings go and my conventions, I cn´t see anything wrong with it (as long as he is happy! And, probably, he will grow out of it, if he´s alloud to “live it out”, so to speak!
    Yesterday, he came to our house to play with our son and it was an amazing sight! (my son was a little bit aquad with the situation though, even if he likes him a lot!) He came dressed in a pink, pleated skirt (and a white petticoat underneath), white tights, white girly sandals, a blouse and long, light blue, also pleated coat! To go with this; the most lomg, blond, curly beautiful hair you can emagine - all the way down his bum where it laid in a beautiful cascade of curls!!! I could hardly beleive my eyes! But, he was really cute and I couldn´t be more stunned but in a positive way!
    A mother with a new outlook on gender outfits!


  13. If my son wanted a skirt he can buy it whenever he starts making his own money. But as long as I buy the clothes, it’s not happening.


  14. First of all, Robin Ashton, that is such a cute story about how
    the little boy who is your neighbor’s son. I always wondered
    too; why can’t boys wear skirts?? After all, little girls wear
    pants and overalls and longalls, and that was supposedly for
    boys, right??

    Next, everything now of what I am going to say is to everyone
    that reads this. I happen to be 31 years old, and I have high functioning Autism. I have several rare and unusual hobbies, including oldies music from the 1950s and 1960s. I also happen to collect vintage t-strap, English sandal, and Mary Janes shoes as a hobby. I have 70 pairs of shoes in my collection, and I’ve been doing this for 12 years. I have many brands that no longer exist anymore, for example, Mother Goose and Lazy Bones. Most of my shoes in my collection are between infant size 5 and preschooler size 12 (which would be for a 5-6 year old).

    If you go down to the Deep South (Georgia, South Carolina, North
    Carolina, etc) you will find that many little boys wear t-strap and English sandal shoes along with pretty little soft longalls such as Kelly’s Kids and Fast Friends. To me, a little boy wearing t-straps is much more ADORABLE than a little girl wearing them. Usually little boys in the South wear the longalls and shoes to church or other functions, and some for everyday use. Out of my 70 shoes in my collection, about 7 or 8 were worn exclusively by toddler boys, and not girls. I’m from Central California, and I’ve lived in California for 29 years and I have never seen little boys dressed like that here in California. But
    it is relatively common in South Carolina and Georgia. A lot of people on the West Coast think t-straps/English sandals are only
    for little girls, but that’s not true. I never had a pair of my own to wear when I was a toddler or preschooler (and believe me, I would have moved Heaven and Earth to get one), because my mom thought they were too girly. Ironically, I have a 38 year old cousin who lives in Portland, Oregon who wore them as a child in
    Hong Kong in 1970-1973. (I’m Chinese-American, by the way). And
    English sandals can go well with anything!! I saw little girls here in California back in the 1980s when I was 9 or 10 years old even in amusement parks wearing jean overalls and English sandals!
    And then, you’d see girls dressed in dresses but wearing sneakers!
    Amazing. Anyway, now, I guess I made up for my loss…I have a huge collection of children’s Mary Janes/T-straps/English sandals.
    Actually most of the time I find them on Ebay, they are listed as “Mary Janes”, although English sandals actually have two straps across and a vertical center strap plus 2 buckles, whereas in theory Mary Janes only have one strap across the ankle and one buckle. Oh well, I guess I’ll save my shoes too - if I ever have
    a son he will wear them. Of course, I’m planning to eventually
    relocate to Upstate South Carolina, where it would be much more acceptable. :-)

    I am selling some shoes on Ebay and will be selling more in the next few months. Look up “English sandals” and you might find
    some stuff. I bought 70 pairs from a store in Maryland (the
    shoes are Foot Traits and Fleet Air, and are all english sandals).
    I’m planning to sell them all on Ebay….I might keep a few though :)

    It’s too bad most of the English sandals were not made in a bigger
    size, after size 12 or so. I have so many brands of shoes in my prized collection: Stride Rite, Jumping Jacks, Buster Brown, Amilio, Footmates, Foot Traits, Child Life, Child Stride, Toddletime, Alphabets (a Belk Dept Store brand), Child Stride,
    Baby Deer/Wee Walker, Mother Goose, Lazy Bones, Red Goose, Kesco,
    Baby Jacks (was a part of Jumping Jacks), and so on…I could go on and on. I’ve actually been told by the president of Kesco/Amilio (Kepner Scott) that I should write a book about Mary Janes and T-straps. Maybe I will. LOL.

    I wish I was small enough to wear English sandals or longalls now,
    but I will never be the size of a 4 year old again :( LOL. I’m
    5 feet 11 inches

    Greetings and Best regards
    Preston from California


  15. Also, I want to add that I never knew little boys could wear
    double buckle t-strap english sandals until about 1998. Then
    I saw in a lot of old parenting magazines like Parents and
    Working Mother and American Baby, and I saw lots of photos in
    them of boys wearing t-straps. It was much more common than I
    thought it was. It was even more frequent in England. Princess
    Diana’s wonderful two sons (bless her heart), Prince William
    and Harry also wore t-straps and Mary Janes. So did John F.
    Kennedy, Jr. too, about a year after his great father the President was assassinated (so about 1964). Anyway, my whole point is that a lot of people here in Calif. feel that t-straps
    would be way too girly for boys, but it’s common in the South.
    So this is similar to the idea of boys wearing skirts since skirts are for girls, and also t-straps were viewed as for girls.

    And I have a BA degree in Geography so that’s why my name is Preston the Geography Whiz Kid. lol.

    Preston


  16. Concerning the article about the little boy wanting to wear a dress. I have two brief points:

    1. They are now making men’s skirts-at least one can purchase these type items on the internt online stores. As a kilt wearer and male skirt weater, I see nothing at all wrong with guys wearing a male skirt. The garment is created for males with the male frame in mind. These skirts are not design for women. As for the kilt, that is a man’s garment period………

    2. Concerning the little boy wanting to wear a dress. First of all, it’s totally normal for little boys to want to dress up in girls cloths. This stupid notion that males are just happy as a lark wearing boring pants is anything but true. Ladies, would you ever,ever consider just wearing one type of garment til the day you die? Well we males feel the same. No and double no,however, I would prefer to see that little boy in a boy’s kilt and not a girl’s skirt.Perhaps mon could have a seamstress make him a skirt and indeed a dress. It would be made just for him and it would be a male skirt. If he desires to continue the unbifurcated wearing of skirts, kilts etc when he gets older, then your child could look into skirts for men.

    My point is that I believe a male should not be wearing girls clothes but that he should be allowed to wear skirted type garments.

    As a little boy, I wanted to wear a skirt but would never confront my parents. I did not know anything about kilted clothing until a bit later in life. I have been wearing kilts for seventeen years and just love it.
    john


  17. Concerning the article about the little boy wanting to wear a dress. I have two brief points:

    1. They are now making men’s skirts-at least one can purchase these type items on the internt online stores. As a kilt wearer and male skirt weater, I see nothing at all wrong with guys wearing a male skirt. The garment is created for males with the male frame in mind. These skirts are not design for women. As for the kilt, that is a man’s garment period………

    2. Concerning the little boy wanting to wear a dress. First of all, it’s totally normal for little boys to want to dress up in girls cloths. This stupid notion that males are just happy as a lark wearing boring pants is anything but true. Ladies, would you ever,ever consider just wearing one type of garment til the day you die? Well we males feel the same. No and double no,however, I would prefer to see that little boy in a boy’s kilt and not a girl’s skirt.Perhaps mon could have a seamstress make him a skirt and indeed a dress. It would be made just for him and it would be a male skirt. If he desires to continue the unbifurcated wearing of skirts, kilts etc when he gets older, then your child could look into skirts for men.

    My point is that I believe a male should not be wearing girls clothes but that he should be allowed to wear skirted type garments.

    As a little boy, I wanted to wear a skirt but would never confront my parents. I did not know anything about kilted clothing until a bit later in life. I have been wearing kilts for seventeen years and just love it.
    john


  18. Concerning the article about the little boy wanting to wear a dress. I have two brief points:

    1. They are now making men’s skirts-at least one can purchase these type items on the internt online stores. As a kilt wearer and male skirt weater, I see nothing at all wrong with guys wearing a male skirt. The garment is created for males with the male frame in mind. These skirts are not design for women. As for the kilt, that is a man’s garment period………

    2. Concerning the little boy wanting to wear a dress. First of all, it’s totally normal for little boys to want to dress up in girls cloths. This stupid notion that males are just happy as a lark wearing boring pants is anything but true. Ladies, would you ever,ever consider just wearing one type of garment til the day you die? Well we males feel the same. No and double no,however, I would prefer to see that little boy in a boy’s kilt and not a girl’s skirt.Perhaps mon could have a seamstress make him a skirt and indeed a dress. It would be made just for him and it would be a male skirt. If he desires to continue the unbifurcated wearing of skirts, kilts etc when he gets older, then your child could look into skirts for men.

    My point is that I believe a male should not be wearing girls clothes but that he should be allowed to wear skirted type garments.

    As a little boy, I wanted to wear a skirt but would never confront my parents. I did not know anything about kilted clothing until a bit later in life. I have been wearing kilts for seventeen years and just love it.
    john


  19. Well this is an odd question for many reasons. First of all being of Scottish heritage I own and wear my kilt. Dinner parties, festivals, social gatherings and yes even out to other events. I’m very proud of it and don’t think it is at all girly. My son is also part polynesian. Lots of skirt like clothing there. How do I tell him that skirts are wrong for boys to wear when it is part of both of our traditions.

    I actually can’t wait for him to be old enough to wear either of the garments. To pass on our heritage and also the comfort of wearing a skirted attire. Not to mention when he gets older, a kilt is a great conversation piece.


  20. come on, this is one of the problems of the problems with the world today. yes, a boy should be a boy, and this includes dressing as a boy. A woman wears a dress because it is pretty and feminine. why in the world would a boy wear a dress? did God create a man to be feminine? i don’t think so.


  21. Preston from California, I haven’t seen boys wearing strap shoes lately in the South (I live in Tennessee). I know the J-Ray Shoes in Mobile, Alabama still sells tradtional “English Sandals” on their boys’ shoe page, so some boys must be wearing them.
    These shoes are also available in adult sizes at Muffy Enterprises on the Internet (they specialize in saddle shoes), if anyone is interested.

    I’d love to discuss details of your shoe collection. I can be reached at bllbolen@netscape.net if you wish to chat. I’m also a geographer.


  22. What did you end up doing??

    I had a little boy. He’s 17 now. When he was about 5, he asked for a nightgown. I figured no one would see, so I let him pick one out from the store. He was perfectly aware it was odd, and didn’t want to even go into the girl section, so I said if anyone asks (knowing they wouldn’t) I’d say we’re choosing a gift for your cousin. He chose a blue one that looked more like a long t-shirt than anything else, and wore it to bed and around the house for years to come; but that was only in the house.

    I also bought him a no-name brand ‘barbie’ doll when he wanted one, I chose one with camping gear. Within a few days she was naked hanging from somewhere, and he never cared much for it after that. I also bought him an ‘easy-bake’ oven, figuring of course boys should cook.

    I’d let him wear a skirt in the house, explaining that while there’s nothing wrong with boys wearing skirts, other people believe it’s wrong and you don’t want him getting his feelings hurt. Teach him about cultures that wear them, and explain that your culture doesn’t (and that in mom’s culture it’s even a ‘bad’ thing), but he can pretend in the house, or be comfortable or whatever. He’ll probably wear it happily around the house, then pass through the phase, or find a way to wear one in a more acceptable way when he gets older. (kilt in a bagpiping group, martial arts where they wear the philipino one, acting on stage as a woman, etc)


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