My Teenage Son Likes To Wear Dresses – Should I Be Worried?

Our children are exposed to completely different circles than we were growing up, and it’s easy to find yourself caught off guard when they do things you never even considered trying at their age. Boys wearing dresses is much more accepted now than it was decades ago, but what their fashion choice means can be a complicated question to answer. Should you view it as a cause for concern?

You shouldn’t – it’s simply an exploration of their identity in the same way a person would pick up hobbies, character traits, or other interests. What makes it scary for you now is unfamiliarity, but that will be diminished over time. Hold off on snap decisions you may end up regretting. Let your son consider these questions for themselves in a safe space. That said, be sure to warn them to be mindful of others who won’t be near as accepting.

It can be difficult or even overwhelming to deal with at first, but don’t let impulse dictate your actions. It’s not an exaggeration to say that your son’s emotional wellbeing hinges on how this plays out, so be careful with how you choose to proceed here.

Calm Down, Take A Breath

It’s only scary because it’s a new paradigm in your life, but it will pass. Your son isn’t choosing this to make your life difficult – what they’re doing is something they’re genuinely interested in, so treat it as you would them coming home with a new hobby: with plenty of support and encouragement.

A lot of parents get taken aback by this revelation and start to wonder where they might have gone wrong. There’s nothing wrong with boys wanting to wear dresses. Even if you do view it as a concern, wouldn’t it be better to glean some more information to see where their new fashion interests are coming from? Focus on how they feel first.

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Mutual understanding and trust are the best tools to diffuse family issues before they escalate. Acceptance is best, but not every parent can do so from the get-go. There’s no shame in not being able to accept new developments like this immediately, but you will have to put in the effort to welcome them for who they choose to be. Tolerance alone won’t cut it if you truly love your child.

Don’t Do Anything Rash, Let Them Lead

dad son talking

What your son chooses to wear is a huge part of their self-expression, and it takes genuine courage and vulnerability for them to do so in front of you. Hampering or even punishing them for showing this much trust is liable to make them take that away, not to mention leaving them feeling even less accepted. The last thing they want is knee-jerk outrage – the first thing they need is validation.

Approach this as something to understand, not a problem to be fixed. Doing the latter will lead to an abundance of problems, and will inevitably strain the relationship you have with them.

Instead, have them share their thoughts on the choice. At younger ages, your son may not even be able to articulate why he’s dressing the way he does or what he gets out of it. Give them the benefit of the doubt, and focus on providing a nurturing environment for them to figure all of this out for themselves.

What It Could Mean…

Your son could be exploring their gender/sexual identity

The transition from childhood to adolescence is one marked by curiosity and discovery, with gender identity being one of the broader topics for them to explore. It’s not something that out of the ordinary – an estimated 1.4 million American children between the ages of 13 and 17 identify as transgender.

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Being transgender is not a problem, but neglecting that identity is. Gender dysphoria is a condition of clinical distress when one’s gender identity diverges from the sex they’re assigned at birth. Wearing dresses – or acting with other feminine-perceived interests – could be their initial attempt at reconciling this gap. Just let them do this, as it’s a paramount need for their emotional health.

Your son could also be gender-fluid or non-binary. They’d hold little regard for societal preconceptions of gender, prioritizing the need to learn more about themselves – their preferences, identity, and sexuality chief among them. The best way to support your son is simply to let them do all of that at the pace they please.

Someone exploring their gender identity and/or sexuality will be most appreciative of the safety their parents and household can provide. Taking that protective boundary away will stunt both their identity development and emotional resilience. It cannot be overstated just how much this exploratory phase means to your son, so kindly let them have that security in their lives.

Your son might be into alt-style fashion

fashion dress person

While non-conforming fashion usually comes with dabbling in identity exploration, gender and sexuality aren’t always involved – your son could just like how he looks in a dress! It might seem an odd trend for you, but acceptable fashion has a habit of changing significantly through history. We’ve got just the example below to show how arbitrary it all is.

For a time, women in the USA were effectively barred from wearing pants – girls who did so in schools were sent home while working women could be kicked off company premises without pay. This absurd ruling even extended during chilly autumns or frigid winters, to the point being able to wear pants was a legitimate incentive some companies used for recruitment.

At the time, pants for women were considered alternative fashion. What might seem absurd now just needs time to settle in – your teenage son wearing a dress will eventually end up as a normal, mundane thing in your life.

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And who knows? Dresses for men could very much be the new vogue in a decade or two – your kid could just be ahead of the curve!

What You SHOULD Be Worried About

pointing judging person

When it comes to non-conforming behavior, you need to consider how others in your child’s environment might treat them. While prejudice is a big issue, most people don’t go out of their way to be cruel. A lot of those misgivings stem from a lack of understanding and communication, and the best way to go about mitigating that is by clarifying misconceptions where you can.

Take your son’s school environment as one example. Try to schedule a meeting with their staff to explain your son’s needs – this gives them both the time and opportunity to figure out the best method to support your son. This also provides them with ample warning about what others might say or do to give your child a harder time.

While that will help significantly, you won’t always be able to prep their environment to welcome them. Your son must be able to assert himself even when he’s alone, so teach them to not be ashamed of who they choose to be. Other kids – or even authority figures, at times – may humiliate them for being different, or even threaten them to change.

The best way to deal with prejudiced people depends on circumstances, but your child will learn how to navigate this in time. As a parent, your main priority is making them feel accepted, accompanied, and loved.  Make them feel they deserve all of that and more.

Final Thoughts

Your teenage son wearing dresses isn’t a cause for concern – it’s simply them exploring their own identity. Process your circumstances carefully before acting, and prioritize providing reassurance to your child. What they need most now is a safe space while they begin realizing things about themselves – regardless of what they learn, they’ll still be your lovable little son.