My 14 year old stepson wants to wear boxer shorts.


At the beginning of the year, I started to do the family laundry to help my husband with the household workload. I discovered something disturbing. I found out my 14 year old stepson wears a certain type of underwear - boxer shorts.

I talked with my husband about it. He said my stepson only recently switched from briefs to boxer shorts about 2 years ago. After a lengthy discussion with my husband, I was able to persuade him that I can switch my stepson's underwear back to plain white briefs and he would support me on this decision. My main reasons are for the family's well being.

First, according to my husband my stepson is circumcised. Based on my research, circumcision exposes a very sensitive part of the body. I believe briefs would be better suited in protecting this sensitive area in a growing boy. Briefs are tight fitting meaning it will keep that sensitive part of the body from constantly moving around. I can't even imagine the type of massive irritation that can happen when that sensitive part of the body is constantly rubbing against fabric every minute of every day.

Second, boxer shorts are more expensive to buy and replace. For example, going to the website for the store Target, anyone can see that a 5 pack of boxer shorts is about $20.00. That same $20.00 can instead get you a 10 pack of briefs. In a clothing store near my area, the cost for one pair of boxer shorts is $3.00 - $5.00. For the same price in that same store, I can get a 5-10 pack of bargain briefs.

Third, based on personal experience boxer shorts are associated with gangs, crimes, and generally shady people. In almost every movie and TV show I've seen gangsters and criminals wear sagging pants with their boxer shorts hanging out or partially exposed. This isn't just isolated to the media. Growing up I have been met a variety of people in the spectrum of life. All jerks and unsavory characters I have witnessed all have had boxer shorts puffing out their pants. None of those people have had briefs sticking out their pants. We are just a white middle-class family. I prefer not to have that kind of negative social stigma associated with my family.

Fourth, this might increase the bond between my husband and my stepson. My husband wears briefs and now my stepson will also be going back to the same. You know the saying "Like father, like son".

Fifth, boxer shorts is underwear for men. A growing teenage boy shouldn't be wearing underwear meant for a fully matured adult man.

What I did

I bought 20 pairs of plain white briefs for my teenage stepson. After doing the laundry, I went into his room, took all of his boxer shorts, and replaced them with the briefs. I placed all the boxer shorts into a plastic bag and dropped off the bag in a clothing donation bin 3 blocks away. When my stepson found out what I did he wasn't happy. He looked more hurt and his eyes teared up a little, but he wasn't crying or anything like that. He just had this sad expression on his face.

I told him my reasons on why I did it as stated above. He says he wants to wear boxer shorts. I asked him why and he said I wouldn't understand because I was a woman. He tried to go to my husband about what I did but my husband backed me up.

I thought my stepson would accept the change and be back to normal after a few days, but he seems stuck in this sad and withdrawn state of mind. I periodically ask him what's wrong and he keeps bringing up the boxer shorts thing. It's been about 8 months now and I don't know what to do to get him back to his old self.

Should I let him wear boxer shorts? I have good reasons for not allowing him to wear boxer shorts as stated above. I can't find any real benefits to boxer shorts over briefs. I tried asking him for his reasons but he said I wouldn't understand because I'm a woman. Do boxer shorts really mean that much to a teenage boy?

I'm not sure what to do.


Thank you everyone for all the feedback.

I read through all of it and did further research into areas I was ignorant on. Yes, I admit I do not know everything but I am open to learn and to correct any misconceptions I might have had.

As a new stepmom ( and first time mother and to a teenager who is a young man ), I let my eagerness to make a positive change to the household blind me from the possible detrimental effects my change might cause.

I have talked with my husband and stepson. The 8 month long tension appears to have been finally lifted. I'm driving my son tomorrow to an outdoor mall near our area so he can pick out a total of 20 pairs of boxer shorts he wants from any of the stores that might be open such as Target, The Gap, American Eagle, Nordstrom, Eddie Bauer, etc. Since this was my mistake, I'm paying for all of the boxer shorts no matter the price. I'm going to donate all the briefs I "forced" on him.

I've learned switching from briefs to boxer shorts for a teenage boy isn't just a change of clothing. It also means he has matured from a child to a responsible young adult where he has earned his parents' trust. It seems to be the modern "rite of passage" into adulthood. I've also learned that boxer shorts appear to play a significant role in the social hierarchy among high school boys. Below is just one example I found doing further research into this: https://youtu.be/wE64QzylZOk?t=85 (American Dad episode)

I can see how hurtful it was to deny him something this significant because I didn't know anything about it.

I also learned this: "At puberty, a boy's needs change to very loose fitting underwear (except during activities)" http://pediatric-house-calls.djmed.net/puberty-underwear-boxers-briefs-or-commando/

I want the best for my son. If boxer shorts give him the confidence and unspoken respect among his peers to be able to successfully socialize & network in high school I'm all for it. These are skills that can translate well into college and into the real world.

Thank you for making me realize my perception of the situation might have been drastically different to others. I don't want to be end up being the mother in the clip below. https://www.dailymotion.com/video/x7vyt1z (Malcolm in the Middle episode)

You live, you learn. :)

You should have seen how happy he was. He was back to his smiling and confident self again. :)

  • 3
    As an example for why I didn't want to wear briefs. I was bullied for several months when other kids in my swimming class saw that I "still wore briefs" at the age of 10. I was perfectly comfortable wearing them, but bullying still pushed me towards boxer shorts, so "Do boxer shorts really mean that much to a teenage boy?" is certainly a complex question Commented Sep 3, 2020 at 12:51
  • 4
    Underwear choice is a personal decision to be respected. Would you allow him to dictate your options in bras? Commented Sep 3, 2020 at 14:29
  • 1
    When did you marry his father? Was your goal to completely ensure that you have no loving relationship with this teen? As for the circumcised part being sensitive, if he was circumcised as a baby, it is healed (Source: Personal experience and I am a pediatrician.)
    – Damila
    Commented Sep 3, 2020 at 18:37
  • 1
    @Tiffany - "I'm going to donate all the briefs I "forced" on him.". Who wants pre-worn briefs? Or are they new unworn? Commented Sep 7, 2020 at 17:33
  • @MichaelHarvey: At least for children's clothing, where I live (Germany) it is common to sell (and buy) used clothing, including underwear, usually at special flea markets for children's stuff. I don't see a problem, as long as you wash them properly.
    – sleske
    Commented Sep 17, 2020 at 7:19

5 Answers 5


Almost all of the arguments that you give for forcing your stepchild to wear briefs sound like reasons to let your kid wear the underwear he wants.

  1. You (a woman) have no personal experience with boxers versus briefs. Shouldn't he (the person actually wearing the clothes) have more understanding of what is comfortable or uncomfortable? By denying him agency over something so small and intimate you have no experience with, you're showing you don't trust him. I can imagine him feeling violated that you are trying to control something so intimate.

  2. Boxers are slightly more expensive, but you also got rid of all the ones he already had. If money is tight, this is an opportunity to teach your stepson about budgeting. If he has an allowance, maybe he would think spending some of it on boxers is worth it Getting rid of something he already had because it was marginally more expensive doesn't teach fiscal responsibility, it teaches him that saving doesn't matter because his stuff will still be stolen.

  3. Plenty of non-gang members wear boxers. Professionals making six figures, etc. Boxers are more a sign of masculinity in general than any specific occupation or class. Some people think briefs are more feminine, which is something you as a woman might not understand.

  4. Underwear is not an area where a child would want (or should want) to bond with their parents.

  5. Your stepson has been wearing boxer shorts for two years. You made him go back to wearing that you consider more childish underwear without consulting him. This makes it seem like you are taking away something he has already earned for no reason. If you treat someone like a child, it makes sense that he would revert to one.

I can see how your stepson might see you taking away his boxers as an incredibly invasive violation of his privacy and a huge red flag that you might be overly controlling in the future. Not only that, but as the boundary was his underwear he's literally constantly reminded of it.

  • 5
    As a circumcised man I can confirm I'm much more comfortable in boxers, and I'm definitely not a gang member. Your post hits all the right points
    – Rory Alsop
    Commented Sep 3, 2020 at 13:06
  • 3
    I am a 68 year old legal professional in England, and I wear boxers. I promise I am not a gang member. Where the hell does this lady get off telling her new stepson aged 14 what underwear he may wear? For God's sake! Commented Sep 7, 2020 at 17:29

Let's take a moment to break down what happened here, from your stepson's perspective. You come home and all your underwear has been replaced. This is underwear you were comfortable in, underwear you had been able to wear freely for two years. Now you have nothing but briefs, something you left behind long ago. Boxers were, in some measure, a part of transitioning out of childhood and into being a teenager. Now that has been taken from you.

He probably feels violated right now. With no warning his world was turned upside down. You didn't consult him or ask him about it. You just took over and changed something you didn't like. He probably didn't (and still doesn't 1) care about your reasons.

He probably feels micromanaged, that any decision he makes can be overridden at any time for any reason or for nothing more than a whim. He has no choice, no agency. He also has no advocate and no voice. He never got the chance to plead his side, to state his preferences. On top of that, his father, someone who should always have his best interests at heart and should be his advocate and defender did none of those things. He didn't say "hold up, let's talk to Stepson about this" or "I hear your objections to this, let's talk about this, maybe we were too hasty". He probably feels betrayed, like he lost an ally and a confidant. (Side note: I'm all for parents being unified but they also need to be an ally to their children as well.)

So now he probably feels like he's living in something like a police state. No real agency, no allies, no voice. I can't imagine being happy living like that.

The point here isn't the boxer shorts. It's the violation of trust. If you want to fix this, you need to apologize first and foremost. You and dad both need to acknowledge that you acted hastily, without consulting with your son over something small but very personal. You are going to have to work to rebuild that trust. It's going to be hard. You are going to have to treat him like the almost-adult that he is. Give him some agency and responsibility. Make him part of decisions that affect him. Trust him. And show it. Value his opinion. Listen to him.

1 I don't want to argue the validity of your reasons here because the reason for the change really isn't the point. It's how you went about it. That being said, you may want to re-examine your reasoning. Much of it to me feels like the decision was made first and the reasons came afterwards to help justify the decision. Most of those reasons are debatable or weak in my opinion.

  • 1
    +1 for "from his perspective". @Tiffany Imagine being a teenager and finding out your (new?) stepdad had thrown out all your underwear for being too slutty and adult because it wasn't plain white or had lace. Wouldn't you feel angry, violated, hurt, and even creeped out? Would you feel comfortable justifying your choice in underwear after the fact?
    – Kat
    Commented Sep 3, 2020 at 3:22

Summary: You should let him choose his own underwear.

Speaking as an adult male, for me some types of underwear are just uncomfortable. There are several other reasons he may have for wanting to wear boxer shorts, like better agility at sports for example. At age 14 he should know best which type of clothing fits him best, or at least this is the right age to figure it out.

I (European) do not have any negative associations with boxer shorts. Like briefs, they are a very simple part of clothing and yet at the same time very intimate. At his age I probably wouldn't have appreciated a conversation with my mother on this topic. However, throwing his clothing out without consulting him first would have felt to me like a breach of privacy and I would also have felt humiliated.


Should I let him wear boxer shorts?

The core of the question is right here so I'll answer that with a hypothetical afterwards.

Yes. In fact, it's not even a matter of you letting him. It wasn't up to you to make the change in the first place but the damage is now done.

Hypothetically, if you came home and found your husband had replaced every single piece of your wardrobe with items he thought were more "appropriate and modest" for a mother without consulting you, how would you feel?

In our relationships with our children, there are things we can control, things we can advise on, things we can delegate, and things we should leave alone. Underwear falls somewhere within the last three of those four options.


As a (I imagine, from the question, new?) parent of a teenager, one of the things that probably is hardest to learn is to choose your battles. Teenagers are nearly adults, and are able to exert a huge amount of control over their lives compared to younger children. They also need to exert that control; they're only a few years away from being on their own, and if they don't have much practice exerting that control they'll be helpless on their own.

As such, you need to decide if this is something that you feel is truly important.

  1. How confident are you that you're correct?
  2. How important is this? What level of negative outcome will occur?
  3. How important is this to your child?

We can't answer these for you - this isn't a site about what kind of underwear is appropriate for teenagers - but you have to decide them for yourself.

If it were something that you felt strongly about, then you needed to have gone about how you handle it differently. How would you feel if someone went through all of your clothes, threw out a bunch of clothes you liked, and bought you different ones, without telling you, or asking you, or any agency on your part?

Instead, treat your stepson like an adult - but an adult who does have to listen to you. Let him know how you feel. Tell him why it's important he make this change. Tell him what the change entails. Let him speak his mind also, and take what he says seriously. If you don't change your mind based on what he says - that's fine; but explain why. Then, do what you feel is right - but after having a conversation about it first.

Some other advice that's more specific to stepparenting:

  • Read up! This is a hard thing to do, and you should go in fully educated. Find resources online - there are tons of them - that are specific to step-parenting, and read them - a lot of them, not just one.
  • Remember that your partner has a lot more well established relationship with the child than you do. This means that difficult conversations are more easily done by him, and not you. This is hard to accept - you'd like him to trust you instantly - but it's just not how people work. Make sure your partner is on the same page as you, and then let him take the lead when you can. This isn't to say you shouldn't have opinions, speak up, and parent - but parenting is built on trust, and take advantage of that when it's possible.
  • Don't try to change too much. Make changes slowly, instead of quickly, so the teen has time to adapt.

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