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Home • Parenting

How To Let Kids Express Themselves Through Fashion This School Year (While Still Dressing Their Age)

Back-to-school season isn’t just about academics—it’s a key moment for young girls and boys to express themselves through style. Here’s how parental support can shape the experience.
How To Let Kids Express Themselves Through Fashion This School Year (While Still Dressing Their Age)
Courtesy of Shay Sweeny
By Audrey Williams · Updated September 9, 2025
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Our children have more fashion options and access than ever before, and that means as parents, we have more to sift through as stewards of their emerging identities. As I prepared to send my 5-year-old off to kindergarten this fall, I couldn’t help but remember my own first-day-of-school fits: the in-store bargaining with my mom, the night-before planning, the fledgling confidence that followed a successful look.

It’s easy to recall my own style evolution with fondness. Looking ahead at my daughter’s, there’s an added layer of complexity. Marissa Moore, founder and clinical director of Therapy Brooklyn, notes this is an especially common feeling among Black parents.  

“For parents of color, particularly Black parents, they are judged all the time by how their child looks,” Moore says. “And it’s not the same standard for other parents. But that’s much too heavy for a child to hold, particularly a younger child.”

How To Let Kids Express Themselves Through Fashion This School Year (While Still Dressing Their Age)
The author, Audrey Williams, growing up

As a mom of two and licensed mental health counselor who focuses on helping families, she’s aware of the way social perceptions can impact parent-child dynamics, especially during the formative years of identity development. Instead of letting these dynamics get in the way, Moore suggests parents interrogate them.  “If there’s any resistance to what your child wants to wear, ask yourself where is it coming from?” she says. “Are there any internal biases or concerns that are flowing through your mind about how they’ll be experienced?”

This kind of parental anxiety was familiar for Yhanni Durdin-James; her four kids, two boys and two girls ranging in age from 12 to 6 are models. In campaigns for retailers like Walmart, Target and Old Navy, they’ve gone from set to set, being styled and placed in the spotlight. To combat the pressures of that, she’s become an advocate for their expression in front of and behind the camera. 

“I spent a lot of time with my kids, seeing them fully express themselves in what they were wearing and how they decided they wanted their hair done,” Durdin-James says. “I realized that I could not worry more about the adult gaze—which is very judgmental to children and parents—more than I worried about my kids. I can’t bring myself to care about that perspective more than I do my own child’s.” 

Instead, she follows an “expansive” philosophy that allows her kids to experiment. Her oldest, Judah, has sensory preferences and only dresses in soft, comfortable fabrics. Her eight-year-old twin girls Echo and Nali have always been encouraged to dress independently. Echo prefers “sporty sparkles” while Nali is a “complete princess.” Amanu, the youngest, is the most experimental, wearing business casual ties and button downs one day and trying on a sequined dress and heels the next. 

How To Let Kids Express Themselves Through Fashion This School Year (While Still Dressing Their Age)
Yhanni-Durden James and family, courtesy of the subject

“In those moments when the kids are taking their self-expression to the next level through their fashion choices, I do have to remind myself to lower my reaction and ask a lot of questions,” Durdin-James says. “What do you like about that skirt? What do you like about those shoes?” 

Moore says this question-led approach is integral to helping your child develop a sense of style you both can feel safe with. “Leading with curiosity and availability will ultimately help a child have a stronger sense of self and connection, and if we’re looking way down the road, they’ll feel like they can come to you with the things that they need,” says the certified therapist.

For parents with more apprehension around their children’s back-to-school style explorations, allowing that level of freedom can feel like a loss of control, but it doesn’t have to be. Stephanie Andrea is an LA-based stylist who has worked with Beyoncé and Jay-Z’s children, styling Blue Ivy, Rumi, and Sir Carter for their personal wardrobes. She recommends creating a capsule wardrobe for kids to meet them in the middle.

“Pouring into whatever the child’s interest is, that’s important,” Andrea says, “but also, you don’t want them to look, for lack of a better term, a little crazy.”

Try building a wardrobe of foundational elements. Think denim, sweaters, matching sets, a variety of T-shirts. That way you can give them free reign to create their own looks with pieces that have already been pre-vetted. “That’s what makes it easy: it’s interchangeable,” she says. “And it’s easy not only for the parent, but also for the child.” With a few accessories of their choosing, Andrea believes a capsule wardrobe is a smart way to bridge the gap between what you want your children to wear and how they want to look. It also works if your child’s school has fashion restrictions. 

As a popular Lifestyle content creator, Shay Sweeney’s style content often includes her husband and three kids in coordinating but never “matchy matchy” outfits. However, during the new school year, Ashton, Aubri, and Averi—10, 9, and 7 respectively—will all be wearing uniforms to their private Catholic school in Houston. “Everyone is wearing the same thing, so pick a shoe or two that you are going to rock and style,” Sweeney told her kids. Her son will sport Adidas kicks while “My daughter, Aubri, she loves pink shoes. Averi has pink shoes with little beads on them. Letting them have fun and still be a kid in their choices is very important.” 

How To Let Kids Express Themselves Through Fashion This School Year (While Still Dressing Their Age)
The author’s daughter on her first day back to school.

Right now, my daughter’s style choices are simple: she wants a skirt that twirls, shoes that light up and kitty ear headbands that sparkle. Giving her that before the world tells her who she should be reminds me that I’m still capable of giving her the creative agency I had to scrape together as a little Black girl.

I’m sure it won’t always be so effortless, but in starting early with conversations and compromise, I’m not just helping her choose clothes, I’m helping her discover who she is.

 “What’s on the other side is a stronger sense of self and self-confidence, which helps them navigate this really scary world,” Moore says. “It allows them to feel a little bit invincible.”

Raising a Style Star 

Licensed mental health counselor Marissa Moore shares how to nurture your child’s self-expression through curiosity, boundaries and encouragement.

Ask questions

Moore recommends starting the back-to-school style convoby asking questions. “I think
what can happen is that kids either divide themselves or get divided by society around what is appropriate, and I think it’s so much better to step back and ask them what they’re
driven towards,” she says.

Establish boundaries 

Whether you have a budgetary limit or a cap on how many new
pieces you want to buy, Moore advises you to “get clear on what your limits are and then have a conversation with your child to say, ‘Okay, this is what we’re doing.’”

Provide options 

Within your established boundaries, Moore suggests offering up alternatives that give your child a sense of control. Say things like, “You can choose three things from this section,” or “Do you want to get your shoes here or there?” as you shop.

Give deeper compliments 

Moore encourages parents to comment on more than just their kid’s appearance. “Celebrate
them for choosing a color that complements them or give them a compliment that is
rooted in strength building, so that they’re not picking clothes just for validation from others.”

TOPICS:  back to school season fashion parenting