What If Back-to-School Clothes Shopping Could Boost Your Child’s Body Image?

Finding back-to-school clothes, especially with a tween, can feel like navigating a body image minefield. Puberty weight gain, pressure to fit in with peers, sexist dress codes—one wrong move feels like it could spell disaster. And that’s before you’ve figured out how to pay for it all.

Maybe you have your own painful memories of suffering in stiff school clothes—or seeing a scowl of parental disapproval as you twirled in a dress you hoped to buy. Stylist Dacy Gillespie told me almost everyone she works with has “deeply imprinted memories of what adults said to them about their clothes, and by association, their bodies. I’ve heard many stories about what mothers said to daughters in dressing rooms. What may seem like an offhand comment can end up being the thing kids remember most.”

Most parents want to avoid sending critical messages about their kids’ appearance. But we can do more than just avoid harm. And this annual wardrobe update presents opportunities to help children build an even more positive body image.

When parents normalize body changes and focus on a child’s comfort and preferences—rather than on what’s "flattering" (more on that in a moment)—kids get to learn a powerful lesson that will serve them their whole lives: clothes should fit your body and not the other way around.

Kids in larger bodies deserve options

If you have a kid in a bigger body, you can feel like you’re shopping on Hard Mode. Michelle, a mom in California, shared memories of the moment when the children’s section no longer worked for her child: “so much trauma around back-to-school shopping for my then-fourth grade daughter who no longer fit in kids’ clothing but still wanted the cute characters.” For kids who need adult-size clothing “but still want Pokémon and Hello Kitty,” Michelle recommends the store Hot Topic. “I remember actually crying when we discovered that option because shopping had been so difficult up to that point.”

When looking for kids’ plus-size clothing, Gillespie urges parents to “make sure you’re not prematurely putting them in adult styles. I’ve heard horror stories of girls who ended up looking like twelve-year-old accountants.” In addition to Hot Topic, Gillespie recommends the brand Justice—no longer its own store (RIP) but available at Walmart—which carries girls’ designs appropriate for elementary school and not a cubicle. For boys, Kohl’s offers a selection of “husky sizes” (yes, that term still exists!). You can also find affordable options for all genders at Old Navy and JCPenney. Lands’ End carries wide size ranges, often with adjustable-waists, including items that often meet school uniform requirements.

Normalize that bodies change—and that sizing is a sh*tshow

Michelle said she and her daughter “have always made a bit of a joke about how ridiculous clothing sizes are even within the same store. I have done my best to take the power out of being a particular size because it is so arbitrary.”

Zoë Bisbing, body image therapist and creator of Body Positive Home, suggests looking for clothes that have some literal wiggle room or fabric with stretch. “I want parents to be thinking, if my child plumped up in the next few months, would this still work for them?”

Gillespie and Bisbing both recommend offering kids multiple sizes to try on. And if your child finds something they really like, consider also buying the item in one size up if that’s an accessible option. This strategy can be especially useful when kids wear uniforms so you have a few items on hand for the next growth spurt.

Children who are bigger aren’t the only ones who find clothing a bit stressful, of course. “There are also kids who are insecure about being tiny,” Bisbing said. “Shopping for clothes can be hard if you're, you know, a 12-year-old boy who is still in size 8. He might not care or he might have feelings about it. Be prepared to notice out loud, like, it's kind of stupid that these sizes are ages.”

Forget “flattering” and let kids find their own style

Gillespie feels strongly about avoiding the word “flattering”—she even titled her newsletter Unflattering—because of its “association with optical illusions that seek to make the body look as small as possible.” And the drawbacks of this term go beyond typical diet culture beliefs about thinness because “the idea of what’s ‘flattering’ is subjective. Trend cycles have a lot to do with it. Millennials might have grown up watching ‘What Not to Wear’ and believe an empire waist is the most flattering thing, but today, oversized everything is more in style. Your kids are probably going to be more in touch with this than you are.”

“Clothing can and should be one of the earliest ways to practice body autonomy for kids,” Gillespie said. Not interfering with our kids’ selections can be tough when their preferences don’t match our ideas of what would look best. Gillespie acknowledges she had to learn this lesson herself: “Listen, I wish I could have kept dressing my boys like little French children forever, but they wanted performance tees and sport shorts, so that’s what they wear.” Letting children take the lead on their fashion choices not only helps them feel better in their clothes but also “contributes to their sense of self and the process of individuation,” she added.

Crop tops can be Kryptonite for parents who otherwise feel strongly about supporting body confidence. “Remember that anything you say could be the thing that sticks with your child for the rest of life, so unless they are truly in danger, try and hold your tongue,” Gillespie advised.

If your child seems happy with an outfit but asks for your opinion, Bisbing offers a line she recently learned: “That suits you.” And she encourages parents to focus on asking questions like, “Does it work for your body? Can you move? Can you jump?” And if kids aren’t feeling it, don’t force it: “Try to make it about functionality, comfort. And if it doesn't work, get it off your body! Like, we don't want that. Only things that work for us here!” These moments prioritize the child’s embodied physical experience over our visual assessment.

Focus on comfort and honor their sensory needs

The number one thing to emphasize is feeling comfy in their clothes. As Gillespie notes, “physical comfort is a basic requirement so kids can run and play and sensory issues don’t distract them when they’re trying to learn.” If fabrics feel itchy, clingy, or just off in some way, clothes also become “a body image irritant” because, as Bisbing explains, “when we are experiencing sensory distress, we are hyper aware of our bodies.” That preoccupation increases body consciousness, making kids more vulnerable to wondering, “What does this look like? Does it look like the way it feels?” In other words, clothes that feel bad on their body can make them feel bad about their body.

Make the shopping experience about more than clothes

Dr. Charlotte Markey, a psychology professor and body image researcher who has literally written the book(s) on this stuff, leans into the idea that “fashion can be fun and doesn’t have to be taken all that seriously.” Her annual ritual with her daughter who loves bargain-hunting sounds pretty darn delightful: “Since she was about 11, we’ve taken the train into New York City every August. She’s given a budget and we look for deals at the huge Old Navy and H&M. We don’t just shop; we get dinner at our favorite Mexican place and walk around Central Park. It’s about getting that elusive first-day outfit but also spending time together.” Finding your own ritual—getting mall-kiosk pretzel bites or going out for ice cream on the way home, for instance—can help build positive associations with the practical task of buying clothes.

Follow their lead—and lower your expectations

Fantasies about bonding with our child while shopping don’t always match up with the reality of the situation, however. Bisbing invites parents to acknowledge, “I want to skip into a department store with my kids,” and yet they may be miserable and you’re frustrated, thinking, “this is supposed to be fucking fun!”

Accept that for some kids, that just isn’t going to happen. “The smells, the lights, the stimulation of the store, the decisions” can be too much, Bisbing said. Your kids may do much better trying things on at home. “If there's a way to give some choice, it’s meaningful to offer some agency in the experience.”

Getting rid of old clothes teaches lessons

Helping kids get rid of things they’ve outgrown not only prevents school morning meltdowns but also acknowledges expected growth and development. Bisbing’s go-to recommendation is to take a Sharpie marker and an old shopping bag and write, “Not working for my body anymore bag.” Making this a matter-of-fact part of family life—maybe you’re adding your own ill-fitting items to the bag, too—is a way of “normalizing and neutralizing what can be a very shameful, confusing experience” in diet culture. “So it's like, okay, just a reminder, we're getting some new clothes, so find whatever doesn't work. You know where it goes.”

Because so many of us didn’t have this kind of body-positive approach when we were growing up, we need to give ourselves grace if we’ve been repeating old patterns up to this point. Bisbing reminds parents that when you’re affirming your child’s size and preferences, “you're breaking a cycle in this moment, you know? It's very empowering.”

Oona Hanson is a writer, educator, and parent coach who specializes in helping families navigate diet culture and eating disorders. A mother of two, she lives in Los Angeles with her husband.