Dressing My Tomboy Teen

by Lisa Rabasca Roepe
Originally Published: 
A tomboy teen standing in the mud in blue rain boots

My daughter stopped wearing dresses on her third birthday. I had been saving a Hawaiian dress with purple and white hibiscus flowers for her birthday party, but when I showed it to her, she stomped her feet, crossed her arms and declared, “I am not a doll!”

She has not worn a dress since. Not for her first communion or her cousin’s wedding or my uncle’s funeral. For her first communion, she wore white pants and a green jacket. She has also successfully avoided wearing a skort for lacrosse by playing goalie, and a long black skirt for band by playing percussion. Her aversion to dresses hasn’t been too much of a problem until this year—the year she and her friends turn 13 and many of her friends are having bar and bat mitzvahs.

She wanted to wear khakis and a long-sleeve T-shirt to her friend’s bat mitzvah, which is admittedly a step up from her typical uniform of cargo pants and a hoodie but certainly not dressy enough. Her compromise was to wear the black pants from her band uniform and a plain blue button-down shirt. That still wasn’t dressy enough.

The only solution was a dreaded trip to the mall, which even I wasn’t too enthused about taking. I prefer to buy my clothes at either Ann Taylor or Loft, or shop online at Garnet Hill rather than wander the mall aimlessly. We eased into our shopping trip by stopping at a cafe for a snack and discussing what colors were acceptable—anything but pink and purple, and no flowers. Thankfully, that left a lot of choice.

I warned her that the juniors’ department might be overwhelming at first, with loud music and frilly dresses, but she needed to keep an open mind. We circled the department a few times, jokingly pointing out frilly strapless dresses with flouncy skirts and sequined tops. We walked across the aisle to the children’s department just in case there might be something there she would like, but it was clear that she had outgrown that department. We took the escalator upstairs to see if just maybe there might be something in the adult section that would be appropriate—at least the choices there might be less revealing. We struck out there, too.

My daughter was ready to give up and happily wear her khakis, but I doubled back to the juniors’ department and asked the salesperson for help. This was Nordstrom, after all.

The salesperson led us over to a section of clothes where she showed my daughter several black and white tops, silky black pants and cardigan sweaters, and suggested we put those together. My daughter reluctantly picked a top with a geometric pattern and a black cardigan, and immediately said she would just wear her black band pants with them. We convinced her to try on the silky black pants, too, just to see how it would all look together.

She ended up liking the pants best—they are loose-fitting harem pants that are probably as baggy and comfortable as her cargo pants. Her other favorite part of the outfit are the shoes. Fancy black high-top sneakers that you put on by unzipping the back rather than untying the laces.

The outfit probably isn’t dressy enough for most bar mitzvahs, but for my daughter, it is definitely a dressy outfit. Most importantly, it fits her style. She looks like a better version of herself, not someone else’s idea of whom she should look like.

When we paid for her new clothes, I asked my daughter, on a scale from one to 10, with 10 being her cargo pants and hoodies and 1 being a dress, how comfortable she felt in her new outfit. Without hesitation, she said, “7.” The saleswoman and I both agreed anytime you can get a comfort level of 7 for a dressy outfit, you are doing something right.

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