Navigating Fashion Choices for My Tomboy Teen

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My daughter decided to ditch dresses on her third birthday. I had planned to surprise her with a lovely Hawaiian dress adorned with purple and white hibiscus flowers for her birthday bash, but when I presented it, she stomped her feet, crossed her arms, and proclaimed, “I am not a doll!” Since that day, she has refused to wear a dress—not for her first communion, her cousin’s wedding, or even my uncle’s funeral. Instead, she chose white pants and a green jacket for her communion, and cleverly sidestepped the need for a skort in lacrosse by playing goalie. This year, however, presented a challenge as she and her friends are turning 13, and many are celebrating bar and bat mitzvahs.

For her friend’s bat mitzvah, she wanted to wear khakis and a long-sleeve T-shirt. While this was an upgrade from her usual cargo pants and hoodie, it hardly met the dress code. After some negotiation, she settled on wearing her black band pants along with a plain blue button-down shirt, but even that didn’t feel quite fancy enough.

That left us with no choice but to embark on what I dreaded most—a trip to the mall. I usually prefer shopping at Ann Taylor or Loft or browsing online at Garnet Hill, but here we were. To ease into our shopping experience, we started at a café, discussing acceptable colors—anything except pink, purple, or floral patterns. Thankfully, that opened up many options.

I warned her that the juniors’ department might be overwhelming, with loud music and frilly dresses, but I encouraged her to keep an open mind. We walked through the department, joking about the strapless dresses with flouncy skirts and sequined tops. We even ventured to the children’s department, but it was clear she had outgrown that section. After a trip upstairs to the adult section proved fruitless, my daughter was ready to give up and stick to her khakis.

Determined, I returned to the juniors’ department and sought help from a salesperson. After all, we were at Nordstrom. The salesperson guided us to a selection of black and white tops, silky black pants, and cardigans. After some reluctance, my daughter chose a geometric-patterned top and a black cardigan, insisting on pairing them with her band pants. However, we convinced her to try the silky black pants, too, just to see how it all came together.

To our surprise, she ended up loving the harem pants—they were loose and comfortable, much like her beloved cargo pants. The icing on the cake was her choice of shoes: fancy black high-top sneakers that zipped up the back instead of needing to be tied. While it might not have been the most formal outfit for a bar mitzvah, for her, it was definitely a stylish upgrade. Most importantly, it resonated with her personal style. She looked like an elevated version of herself, not a caricature of someone else’s expectations.

When we wrapped up our shopping, I asked her to rate her comfort level with the new outfit on a scale from one to ten, with ten being her cargo pants and hoodies, and one being a dress. Without hesitation, she replied, “7.” The saleswoman and I both agreed that achieving a comfort level of 7 in a dressy outfit was a victory worth celebrating.

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In summary, navigating clothing choices for my tomboy teen has been a journey filled with compromise and understanding. Ultimately, finding outfits that align with her comfort and style has made for a positive shopping experience.


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