1. How My Son’s Love For Dresses Challenged Everything I Thought I Knew
Part of the “As Told to Bolde” series. Have a story to share? Contact [email protected]
Meet Rachel, 36. She shares how her son’s love for dresses opened her eyes to the meaning of parenting.
“I never thought twice about my son’s clothes—until he started choosing dresses. I assumed it was a phase, just an innocent curiosity. But when he kept reaching for the sparkly skirts and twirling in front of the mirror with pure joy, I realized this wasn’t about dress-up. It was about self-expression. My initial reaction was a mix of confusion and panic. Would people judge him? Would they judge me?
I hesitated before letting him wear one in public, which forced me to confront my biases. The truth is, my son is still the same kid in jeans or a tutu. What changed is my understanding that parenting isn’t about molding a child into who we think they should be—but giving them the space to be who they are without shame or feae. This was the greatest lessons in unconditional love I never knew I needed.”—Rachel Carter, Denver.
Continue reading to explore more about parenting and letting kids be free to be themselves >>
2. Self-Expression Shouldn’t Be a Battle
What a child wears shouldn’t be a source of conflict, yet for many parents, it becomes one. Whether it’s a boy wanting to wear a dress or a girl refusing to wear pink, clothing choices suddenly become a debate about identity and values rather than just a reflection of personal taste. According to Lion+Owl, giving children the freedom to choose what they want to wear encourages creativity and imagination, and helps them feel more confident in expressing themselves.
Fighting a child over self-expression only teaches them that being themselves is a problem. Instead of seeing clothing as a battleground, it can be a chance to show unconditional support. It’s not about what they wear—it’s about whether they feel accepted in their own home.
3. Clothes Don’t Define Character, But Reactions to Them Do 
Wearing a dress doesn’t change who a child is. It doesn’t make them weaker, less capable, or any less of the person they were before. What does change is how people treat them—and that reaction says more about the adults than the child. As noted by Lion+Owl, allowing children to wear clothes that make them feel good regardless of gender helps break down stereotypes and fosters inclusivity.
Some will react with discomfort, others with praise, and some with outright hostility. But the child remains the same. It’s a stark reminder that prejudice and judgment aren’t inherent—they’re learned and reinforced through reactions that can either affirm or shame a child’s choices.
4. Confidence Comes From Feeling Accepted, Not Controlled
Kids who feel safe to explore their interests grow up confident. They trust themselves, knowing their instincts aren’t “wrong” just because they don’t fit a rigid mold. But when they’re policed into conformity, that confidence gets chipped away. According to Vanilla Bean Baby, when children are allowed to make choices about their appearance, they develop a stronger sense of autonomy and self-esteem.
Confidence isn’t about fitting into societal norms—it’s about feeling valued for who you are. A child who knows they are loved, no matter what they wear, carries that security into every area of their life.
5. Judgment Says More About the Adults Than the Child
Every reaction to a boy in a dress is a reflection of the person reacting, not the child wearing it. If someone is uncomfortable, it’s worth asking why. What belief is being challenged? What fear is being triggered? As Lion+Owl suggests, children learn to care about gender expectations only when they are taught to, and reactions to their clothing choices reflect more on the adults than the child.
Kids don’t care about gender expectations until they’re taught to. If an adult bristles at a boy in a dress, it’s not because the child is doing anything wrong—it’s because the adult has been conditioned to see it as a problem.
6. The Fear Around ‘Different’ Is a Learned Behavior
Children learn fear from the world around them. If they pick up that something they naturally enjoy is “wrong,” they internalize that shame. It’s not the dress itself that’s harmful—it’s the reaction to it.
When a child sees their choices being met with fear or discomfort, they start to believe that being different is dangerous. That belief doesn’t just apply to clothing—it shapes their entire sense of self-worth.
7. Support Means Listening, Not Policing
True support isn’t about allowing something “just this once” or tolerating it until they grow out of it. It’s about listening to what makes them happy and ensuring they feel safe expressing that.
When kids feel like they’re walking a tightrope, constantly monitored for signs of “acceptable” behavior, they shrink themselves. Listening and validating their choices doesn’t mean indulging every whim—it means treating their preferences with the same respect you would give an adult’s.
8. Happiness Should Matter More Than Social Norms
What’s more important—adhering to arbitrary rules or raising a child who feels free to be themselves? The answer seems obvious, yet so many people struggle with this when faced with something outside their comfort zone.
Clothing should be about joy, comfort, and self-expression. If a child’s choice isn’t harming anyone, why should it be discouraged? Happiness isn’t about fitting in—it’s about feeling free.
9. What Feels ‘Uncomfortable’ To Some Is Just Freedom To Others
For many, seeing a boy in a dress triggers discomfort—not because there’s anything inherently wrong with it, but because it challenges deeply ingrained beliefs. But to the child, there’s no conflict. There’s only freedom.
What seems “unusual” to one generation is often completely normal to the next. The discomfort isn’t a sign that something is wrong—it’s a sign that perspectives are evolving.
10. Curiosity Should Be Encouraged, Not Shut Down
Children are naturally curious, and they learn through exploration. Stifling that curiosity doesn’t stop them from wondering—it just teaches them to keep their questions and interests hidden.
Encouraging curiosity, even in areas that challenge norms, fosters critical thinking. It helps kids develop confidence in their ability to understand the world rather than just obeying its rules without question.
11. Kids Know Who They Are Long Before Adults Do
Many adults assume children are too young to understand themselves, but kids often know more about who they are than we give them credit for. The problem isn’t that they don’t understand—it’s that adults don’t always listen.
Instead of assuming they’ll “grow out of it,” it’s better to recognize that they might just be growing into themselves. What they need most is the space to figure that out without fear.
12. Allowing Choice Builds Trust, Not Defiance
When kids feel forced into roles that don’t fit, they either shrink themselves or rebel. But when they’re given choice, they don’t have to fight for autonomy—they already have it.
Building trust with children means letting them make decisions about their own identity. Trust fosters open dialogue, while control breeds secrecy and resentment.
