Buying Dresses and a Skirt for My Son

I wrote recently about my six-and-a-half-year old son Zach asking for a dress. I took him and his friend shopping at Target, and it took all of about five minutes for him to choose one. He seemed uninterested in the brightly colored or frilly dresses. I spotted this dress, and he said he liked it, so I bought it for him. No one in the store even noticed these two boys giddily holding a dress as we brought it to the register.
 
A blue and black dress
 
I’ll be honest, I was really grateful that he chose a dress that’s not really loud or flamboyant. It’s still a dress, but it seems like it’s still his style somehow. I’m not sure what difference it makes, but I’d be more freaked out if he chose a dress that was hot pink or neon green. I still want my kids to dress tastefully.
 
My husband expressed concern when Zach said he wanted to wear the dress to school. He said he’d prefer to take things slowly, just start out by wearing the dress at play dates or the park first. I was initially irritated when my husband talked about how he grew up in a more conservative time, and he’s not totally comfortable with this yet, but when he asked for taking a slow pace and easing into things, I realized that’s a really, really good idea. There’s no rush. Zach’s not begging to wear the dress to school. He said, “Okay, that’s fine.” My husband said that he wants to offer “a safe space to engage in what is a perfectly innocent activity, but protect [Zach], too.” He was worried I would be mad, but I’m really grateful that he’s open-minded about this and cautious at the same time. I think it’s important to be both.
 
I became aware that my instinct is to suppress my own needs or desires and put my children first. I want to do what’s best and “right” for them, sometimes not even stopping very long to figure out what that is. I’m nervous about how people will react to him wearing a dress at school. On one hand, it’s easier for him because his friend has already done it. On the other hand, having two boys wearing dresses at school might create a different bullying situation. Some kids may say, “Oh, you guys must be boyfriends because you both wear dresses.”
 
Zach said he wants to wear dresses because he doesn’t think it’s fair that girls get to wear skirts, shorts, dresses and pants, and boys only get to wear shorts and pants.
 
I looked on Quora, a site where people can post questions and other people, many of them experts in a particular field, can provide answers. I looked up, “Why do boys wear pants and girls wear dresses?” One person said that pants-wearing is strongly connected to riding horseback, which men primarily did for hunting or fighting in battle. He describes how ancient Roman and Greek infantry soldiers wore tunics while Roman cavalry wore braccae, which are basically trousers. In Japan, both men and women wear kimonos, but the warrior class would wear hakamas, which are a kind of split skirt (trousers under a skirt). Men do wear skirts or kilts in Scotland and southeast Asia.
 
My husband suggested getting Zach a kilt. I realized the floor-length dress we’d bought was really impractical for playing outside. So, I went to Goodwill and found this skirt and dress. The skirt has shorts inside. Together they cost less than $9. I intend to have him wear pants underneath and probably a shirt under the dress as well.
 
A beige skirtA blue plaid dress
 
Zach tried them on and said he likes them. He also said it’s okay for me to return the dress we’d gotten from Target. It’s pretty, but really impractical.
 
Does this post change in any way your view of whether boys should be allowed to wear dresses? Why or why not?

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