My Son Wore a Dress

This is a followup to my post “My Son Wants to Wear a Dress”, which can be found here.

As soon as I decided I was just going to let Bennett wear a dress, public reaction be damned, he stopped asking.  Little did I know he was just waiting to raise the stakes.

The next time he asked, we were on vacation in upstate New York, visiting Drew’s family.  This was the day we were going to the zoo.  We’d been talking it up to the kids all week.  Just as we were picking out clothes, Bennett made his intentions known.

“I want to wear a dress!” he chriped, his voice rising an octave on the key word.

As usual, Drew and I kind of stalled.  We’d been hoping we could blur the gender lines quietly at home – at least initially.  Letting him make his drag debut at the zoo might mean throwing him literally to the wolves.

His sister Sutton must have noticed my hesitation, because she stepped in to do the dirty work.  “No, Bennett,” she said.  “You can’t wear a dress.  It’s not OK!”

“Come on, Bennett,” I said.  “Let’s go pick one out.”  I couldn’t control how the rest of the world reacted to my son’s attire, but I wasn’t going to let his own family shame him for wanting to express himself.

As I stripped him of his boy clothes, Bennett couldn’t stop smiling.  “I’m going to wear a dress outside!” he cheered.  “I’m going to wear a dress outside!”

Maybe the kid was more aware than I realized.  So wearing the dress outside was the triumph?  Maybe he wanted to see how strangers reacted.  That’s awfully subversive for a not-quite-three-year-old.

We have a rule with Sutton.  Whenever she wears a dress, she has to wear shorts or leggings underneath.  Being the fuddy-duddy daddies we are, we refuse to contribute to the hoochie-fication of today’s toddlers.  Our little girl wasn’t going to be some primped-up preschool strumpet.

And neither was our little boy.  If he was going to wear a dress, he was going to put something on underneath it.

The problem was that none of Bennett’s shorts really went with the dress.  Neither did his very boyish navy blue sneakers.  He didn’t care.  The dress was all that mattered to him – but not to me.  I didn’t want people to think this was my idea of a flattering ensemble for my son.

Suddenly, I’d be the one getting judged.  “I can’t believe those dads put that poor little boy in a dress… and didn’t help him accessorize!”

He looked silly.  At least I thought so.  To be honest, I don’t think he even checked himself out.  All he wanted to do was dance.

“Twirl!  Twirl!  Twirl!” he shouted, as he spun around again and again, watching the dress float up around him.

Suddenly, I wondered if he got the idea to wear a dress from Beauty & The Beast.  The way Belle dances in the ballroom and the camera zooms in on her gown rising majestically around her — it was so magical.

For Bennett, the dress was a toy he could wear – part pants, part hula hoop.

It was nice to see him so happy, but there was one person who could derail that joy in an instant – and she was waiting for him at the bottom of the staircase.

It was, after all, a vacation.  We’d only packed two dresses.  Sutton was wearing one, and now her brother was wearing the other one.

Her favorite dress.

I was terrified what she would say.  I very cautiously brought Bennett to the top of the staircase.

“I’m wearing a dress!” he trilled, and his sister glanced up for a look.

All of us froze in that moment.  Once again, it was like Beauty & The Beast, right after Belle has been dolled up by the coat rack and miscellaneous flatware.  When the Beast sees her, he smiles, and you know everything is going to be OK.

“You look so pretty!” Sutton squealed.  “Now we’re both princesses!”


Bennett scurried downstairs, and they danced together, twirling and twirling, until they both fell over, giggling.

Drew and I went to the zoo prepared to clock anyone who made a comment about Bennett’s dress, but nobody said a thing.  We were the only ones who were the least bit uptight about it.

On the way home, we stopped for lunch.  Our waitress leaned down to me and Drew.  “You have such beautiful girls,” she said.

I wasn’t sure what she meant at first.  Was she saying what she thought my son wanted to hear?  “Such beautiful girls” – wink!

It didn’t seem right.  He may have been wearing his sister’s clothes at the moment, but my son is very much a boy.  He plays with trains, builds Lego towers, splashes in mud puddles.  He even announced recently that when he grows up, he wants to marry a boy… just like both his dads.  What’s more boyish than that?

When the waitress returned with our food, she made another comment.  “You two fellas are so lucky to be here with such beautiful women!”  I realized she was being totally sincere.  She hadn’t noticed Bennett’s shorts or sneakers, hadn’t thought much about his short hair.  Because he was wearing a dress, she assumed he was a girl.

“Thank you,” I said, “but this guy’s a boy.  He just wanted to wear a dress today.”

77 comments on “My Son Wore a Dress

  1. 1st of all, we have the same dress here in Scroogyland. I think Loopsy wore it for Easter. 2nd, HOO-effin-RAY!!! I’m so glad you let him wear it outside AND that you let the waitress know he’s a male. I’m super proud. And you should be too!

  2. What a wonderful family! You’ve set such a great example for your children, letting them know that you love them for who they are, and letting them be free to express themselves. Your decision must have taken a lot of courage. We know there are people who judge for anything they perceive as different. But still you made the choice to give your son the freedoms to choose his outfit, and it sounds like everyone benefitted. He had a blast, your daughter learned that, yes, it is ok and even fun when her brother wears a dress, and for you and Drew, it must be a huge weight off your shoulders to know that you can take your son in public wearing a dress without problems.

      • It’s hard at first, but if your son continues his love of dresses, it will likely get easier. We live in a very conservative town, and my son had long, wavy hair for nearly a decade. He also loves to wear pink shirts, and has a collection of my little ponies hanging from his bright pink backpack. He has been mistaken for a girl quite often, even well into his teen years. He was embarrassed when servers would ask us, “what can I get for you ladies?”, but as he grew older, servers were equally embarrassed when he replied in a very deep voice. At first, I wasn’t sure how to handle these situations, but I discovered that they handle themselves. Yes, he’s put up with ridicule at school, but on the other hand, he’s learned the importance of getting to know people before making assumptions. He’s also learned what it feels like to be unfairly judged, and he’s able to stand up for people who may appear different. In all honesty, I think having been treated as a girl is turning him into a better man. I suspect allowing your children the right to choose how to express themselves will have the similar effect of helping develop the character trait of embracing individualty.

  3. I find it hilarious to the n-th degree that your greatest concern was the missing/incompetent accesorisation. You are such a girl sometimes, Jerry!!! 😉

    Kudos though for letting the waitress know. I think everyone with kids (and even some of those unfortunate childless creatures) knows that they come up with the craziest ideas. Wearing a dress in public and feeling like a princess at her prom certainly isn’t the most odd, dangerous or outrageous request a little rugrat can make. I think you handled it really well. So now, either the novelty has worn off and Bennett can close the chapter on wearing a dress or, when he next asks to be appropriately outfitted for twirling, you guys will know it’s not a biggie – problem solved.

  4. Okay, as a Dad raising a son, and a Gay Dad at that I have to say thank you.
    Not just for writing this and sharing it but also for showing me that it’s possible to actually be the type of Father I am hoping to be.
    You taught me a wonderful lesson Jerry, just wonderful!

  5. I find nothing wrong with that! Good for you guys letting him be himself. There’s nothing better for their sense of self esteem or confidence.

  6. OK. So, admission time.

    I’m the lesser of the open-minded dads. My stomach was in knots the whole morning we were out with them…and I think I noted EVERY SINGLE double take that happened in the greater Rochester area that morning, especially at the Seneca Park Zoo. People looked at our little guy and (I think) just assumed it was a little girl with a pixie hair cut — and gosh, weren’t we open minded to let HER wear those ‘boyish’ shoes with HER dress?

    I am so lucky that Jerry is even-tempered and more open-minded than me — because I would have to tried to force him to wear something boyish…and I would never have realized that most people…well, it’s hard to say this…most people don’t *really* give a shit about me or what my kids decide to wear (at this age, at least).

    I also feel like I lose some points when I tell you that the RELIEF i felt when he stopped asking to wear the dress was akin to finally peeing after driving for 3 hours and having had three iced teas before getting into the car. (In other words, it was a BIG relief.)

    But I lost more points YESTERDAY when Bennett demanded to wear a dress to one of Jerry’s cousins’ BBQs in New Jersey. I bribed him into thinking it would be cool to wear one of the Threadless t-shirts (just like Jerry wears), and he seemed to be OK with it.

    Who knew that the most biased and uptight judge of my kids would be me, myself and I? (Hang my head…)

    But he does look cute in the dress. And I will throttle anyone who says otherwise.

    • Nervousness about other people’s reactions doesn’t make you less open minded, it makes you human. You weren’t judging your son because he wanted to wear a dress, you were simply aware that other people might judge (If you were judging anyone, it sounds like you may have been judging yourself). It can be doubly difficult for you and Jerry, seeing as how you probably have to face stereotypes the you’re “turning him” this way by the mere fact that you happen to love another men. There isn’t always a “right” decision, and parents have to make choices about what works for their families. The fact that you made the choice to allow him to express himself in this way, even though it made you uncomfortable, speaks volumes for your values of openness. Sometimes, when you know the consequences may be more long lasting, you choose to steer him toward a different outfit. I think it’s ok to acknowledge that some parental choices are influence by other people’s potential reactions. After all, much of our decisions about ourselves is guided by other people’s potential reactions. If this weren’t the case, I’d wear pajamas to work every day 🙂
      So keep up the great parenting, but please, allow yourself to be human!

      • Thanks, Becky! I agree that, whatever Bennett grows up wanting to wear, this experience will build character. I can’t control what the rest of the world says to him, but I can make sure he knows his family supports him.

    • I’ve read this blog post a few times, and showed it to other people, but I never read down into the comments and realized this took place in my hometown! Now I recognize those baboons. And of course Bennett looks adorable with his sister there!

    • Hi this might be weird replying years after the original post but I’m struggling to find help other than extreme opinions from both sides. I read the blog and the comments and I’m going through the same anxiety as a dad with my son. He asked for a dress last year and he wears it everywhere with his leggings. My parents aren’t very supportive but they love him.
      I just wanted to know if there is a followup to your stories. Are your boys still happy wearing dresses? I’m terrified of doing the wrong thing and ruining the relationship with my son but I also don’t want him to go through bullying for something he likes to wear. I don’t think there is a right answer but I liked the honesty that is on here.

  7. Bravo to both of you! Drew, give yourself a break. This daddy business is hard work and you’re doing the best you can. An open mind is a beautiful thing to see in children and adults. And I think you actually earn extra points for your honesty!

  8. I grew up hating to wear a dress….my mother hated that I donned jeans and t shirts and played football with my brother…when I was older and attended black tie events I was the one daughter that showed up in a tuxedo while my sisters “Drucilla & Anastasia” wore their finest taffeta….

    I dressed my daughter in funky NYC clothing from toddler-dom and she now is a Fashionista and wear’s Fru-Fru dresses..

    My son wore his sister’s uniform dress when he was 4 when his sister & friends dressed him up, they laughed & played with Barbies and my son would ram the pink convertible with Ken driving and know down the Dream house…… Now he wears tuxedo’s and Khaki’s…..

    Great story……they are kid’s..enjoy their spirit . Take your son into to Gap kids and let him pick something to wear, have him take it to the cashier and proudly pay for it with the dollars you hand him..

  9. Awesome! Good for you guys! And your children. It’s so important to allow individuality, no matter what age your children are at.
    I wouldn’t worry much about the ensemble. I like when children look well put-together in their little outfits and accessories, but I smile to myself when I see children who have clearly dressed themselves. 🙂

  10. This post made me smile, and made my heart beat a little faster. When you wrote about Bennett wanting to wear a dress, I wondered how you would go about matters the day the event happened. You surpassed my greatest expectations. Well done.

  11. What a wonderfully sweet story. Thanks for sharing. I read the initial post, and I’m so happy to see such a wonderful follow up – and to see that things have turned out so well.

  12. I’m so glad!!

    There are plenty of people out there who look askance at a boy in a dress. There are even more who gender pigeon-hole someone based merely on an article of clothing. Who gives a rip about them? As the comments pass by his ears, he will hear you standing up for him, he will learn to graciously respond and deflect, and by the time he has to stand up for himself – whether its about wearing a dress or holding a different opinion than his peers or making a choice for his own good that goes agains the grain – he will already have great ideas of what that sounds like.

    My Brother-Bug has decided to have a boy name on one day, and a girl name on alternating days. He’s not sticking with his given name either. Today he’s a boy named Ernest. Whatever.

  13. This is the first time I’ve come across your blog, so forgive me if I’m posting something you already know or have written about. There is another (fantastic) blog which I read regularly about a mom and her “gender creative” (her words) son. I thought you might be interested.

  14. Two thoughts – there are more and more kids at earlier ages showing they are the ‘T’ in LGBT (as well as the other letters) and insanely early ages. I know someone who came out as gay at age 3. Even if he likes trucks and stereotypical boy things, doesn’t mean a thing. Wanting to wear a dress doesn’t either. Some girls like boy things etc. If he is going to be a LGBT, he is fortunate to have you support him from an early age.

    The other thing – little boys wearing girls’ clothes is less odd than most realize from a historical perspective. Jefferson Davis, the president of the Confederacy, was in a dress and Cindy Brady curls up until about age 5 as I recall per a display at the Confederate White House in Richmond. It was custom back then to dress little kids as girls (both girls and boys) and have them go commando – easier to manage the bathroom, cleaning etc. In the picture you cannot tell he was even male.

  15. Well at least your little boy want to wear something! I have fond memories of our neighbors across the street in a rather stuffy neighborhood many years back. They had a little girl who delighted in dashing out the front door buck-assed naked and streaking through the ‘hood with her mom in hot, embarrassed pursuit.

    Kids will be kids and thank god your kids can revel in their kidhood. All’s well that ends well, right?

  16. My Mom tells the story of putting me in a lace dress with blue ribbon & getting all the “what a cute little boy!” comments. Thankfully, gender has nothing to do with clothes, so I am happy to say I am still the gender I want to be, not the one everyone thought I was that day – and that’s what’s important, right? 🙂

  17. It is amazing what people think by the clothing kids where, I have a 3 year old daughter who sometimes wears jean overalls over a very red shirt and black superhero sneakers… She loves this outfit, yet everytime we go out. I get what a cute little boy you have. He is so active.. And I simply agree “Yes I am lucky to have her.” People I don’t think really pay that close attention to young children.

  18. You are really a nice dad. Not all dads are like that. Happy Father’s Day! (I even greeted you first than my own dad)

  19. hey, you know what? Here in India, people dont think twice about dressing their toddlers up in drag. In fact there are pictures taken of boys in traditional girls’ attire, complete with flowers adoring the hair and accessories like earrings and bracelets and necklaces – and proudly displayed to any and everyone who cares to come home. They serve as really cute reminders of when the boys were kids and they wore cute little girl dresses! 🙂

  20. Hey, the drummer from Phish wears a dress at nearly every single concert they give, and I dare say no one in their right minds would criticize him for that (even if it’s the same frock at every show 🙂 ). Good on ya, dads! Cool blog.

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  23. At contra dances (a form of folk dancing, related to square dancing and originating in New England in the 19th century), you can often find a man or two wearing a skirt. Normally they’re on the younger side, but not always. Contra dancing involves a lot of spinning around, and as Bennett discovered, that’s LOTS more fun with a skirt swirling around you!

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  25. I love this. My 5 year old had a meltdown in the middle of Target not long ago because he wanted a pair of pink princess sneakers – we compromised – he got black sneakers and hot pink laces. But I also made sure to pick up a few princess costumes for the costume chest. I think more people should encourage their kids to just be who they are, rather than fit a random Play-Dough mold. Kudos to you gusy for doing what too many other people are afraid to do.

    • Thanks. We’ve since purchased a lot of dress up clothes, and he loves to put on the princess dresses in play time. He never asks to wear dresses outside anymore. He’d rather wear his Thomas the Train tshirts. He did dress as Sleeping Beauty on Halloween, and he often tells us he wants to be a princess. My attitude is, hey, if you’re playing pretend (and Halloween fits under that), you can pretend to be anything you want.

  26. Of course a effiminent genderly confused woman with a penis would allow her son to wear a dress in public! Perfect sense!

    Are you going to teach him drag and learn how to screw all the men at he bathhouse too???

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  28. My son went grocery shopping with me aged 3 wearing a tutu over his trousers and a gold sequined top hat. It was a shop I worked at so the 18 year old boy serving me felt able to tell me I shouldn’t have allowed it. “Why not, he’s 3!” I said. An older (straight) male co worker nodded his approval. I added that it might be a little different if he wanted to wear it in 10 years time.

    I was proud of myself till I told my husband when he came home from work and he replied that if he had the hutzpah to wear that kind of ensemble age 13 then he’d be really proud of him.

    It was hard to tell him age 5 that if he had nailpoish like his sister he might get teased at school (I’m not into make up, I didn’t have remover in the house). We compromised and he had it on his toenails.

    He’ll be 7 tomorrow and he still loves dressing up, waistcoats, dresses, dr’s set, whatever. When his sister gets a party dress for christmas he gets a waistcot and tie. He doesn’t wear dresses out anymore, but he will at home.

    Does it mean he’ll grow up gay or effeminate or a drag queen or a dandy or a fashion designer, or is he just desperate not to miss out on any ounce of fun his sister is having? I don’t know and I don’t care. He’s growing up happy and loved. All I want is for my kids to grow up respecting others and themselves, the rest will follow.

  29. Good for you and not discouraging your son from being who he wants to be and refusing to allow anyone to plant the seed of negativity in shaming him! I too have a son and although at 6 months he doesn’t want to wear a dress, I too would not stop him from wearing one if he so desired to once older! #PROUDPARENTINGMOMENT

  30. I know this is a really old post, but my little boy, who is not so little anymore, wears dresses all the time. I figured it was a phase he would outgrow. Then I kinda assumed he’d be trans. Now, that he’s in jr. high, I just assume he’s a boy who likes dresses. We wouldn’t let him wear a dress to school till this year though. The first time he asked, in 2nd grade, we told him that if, when he is in jr high, he still wanted to wear dresses, we wouldn’t stop him. The second time he asked he was in jr. high, and we said yes. I figure there is some obligation to protect him a bit, cause there was no way for a 7 year old to grasp the concept that not all kids would be nice to a boy in a dress, and until he understood that was a probably outcome we didn’t think he should be making the decision to brand himself for all of school as the boy who wore dresses. That said, we did let him wear whatever else he wanted, which was nearly only girl’s skinny jeans, only girl’s shoes since he was 2 and expressed that he had an opinion about what shoes he wore, and a mixture of button down boys shirts and graphic girls shirts… We let him wear rainbow unicorn pajamas for pajama day and a merida costume for halloween and all that. Now, at 11, getting close to 12, he wears dresses a couple times a week to school, and, yes, some kids have been jerks, but, the school has handled it really well and his english teacher even dressed from head to tow in pink, including a skirt, for a breast cancer awareness day (with a contest for who could wear the most pink, which my son won, and for whose homeroom was wearing the most pink).

    My daughter, who is 13, refused to wear pink, even for a contest. That’s usually how things work. Her first favorite toy was a frog, followed by a monster truck. His first favorite toy was a my little pony…and that is still the case. Their little brothers are much more gender conforming, though, our 6 year old loves his big brothers outgrown nightgowns.

    • Thank you so much for this comment! I loved hearing your story. Your son sounds awesome, and you sound like a great parent. My son is now 6 and still loves to play dress-up, but he never asks to wear dresses outside the house anymore. He’d much rather wear t-shirts with Mario on them. I think kids are happiest when we let them be themselves. They may face resistance from the outside world, but they shouldn’t face it from their own family. Best wishes to you all! 🙂

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  32. Thats a nice dress he wore my son wanted a dress and after reading this I got him one and he ended up wearing it on our holiday to disneyland the funny thing was on holiday a waitress said that I have a beautiful girl which made him say im a boy not a girl. The waitress then said to me that I should let him wear that more often and he did he wore it to disneyland the next day and I even got him an Elsa dress

  33. Our son and daughter are two years apart and when the daughter was 14 and the son 12,they both finially made their First Holy Communions in the class of 2nd graders.The son wore the suit and ty and i dressed the daughter in the traditional,poofy,short sleeve,top of the knees communion dress and veil with the lace anklets and the white mary jane shoes and under her dress i did the white tee shirt and white toddler large size rubberpants,just like the little girls wore.The son couldnt keep his eyes off the daughter all day long! Later that week,the son got home from school and i was out shopping and the daughter was at a friends house.I got home and caught the son wearing the daughters communion dress and veil with the lace socks and the mary janes and he had the rubberpants on under her dress! He told me he liked the way sis looked in her outfit and wanted to see what it was like being like a ‘little’girl! After that,i got some some panties and a couple pair of girly rubberpants and made him wear them for 3 months!

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