Why I Let My Kids Pick Out Their Own Clothes

kids clothes

You’ll often find my children in oddly matched clothing. And if I see you out somewhere, I might offer a hasty disclaimer, “He dressed himself!” (as if you couldn’t tell). My oldest has been known to wear shorts with socks pulled up to his knees, and cowboy boots. My youngest is a fan of the shorts and snow boots combo. I’ve even been known to show up at Awana with spider-man in tow.

Here is my youngest, sporting the plaid shorts + non-matching shirt and cowboy boots option.


So why do I allow this?

My boys are individuals

They are not an extension of myself, they are their own people. I want them to have confidence in who God created them to be rather than feeling forced to follow the status-quo. Doesn’t God’s word call us to be set apart? Why, then, would I want to teach them that the only right way to be or look is like everyone else? That is a dangerous path to follow. We don’t want them to look like everyone else on the inside, and the outside isn’t that important either. Who decided all the “rules” for fashion anyway?

I want them to have a healthy self-confidence. You know what kills self-confidence? Having someone constantly criticize and micro-manage your decisions.

Encouraging Independence

We are training our boys to be self-sufficient and independent as much as possible. Not so that they will think they can “go it alone” but because we’ve heard of too many adults getting out into the world without being able to do basic things for themselves. Both of my children could independently select clothing and dress themselves at an early age, and have been doing so for years.

This is a huge help to me as a mom who struggles with debilitating chronic illness. Such a big help that I don’t mind if they don’t always match.

Because I want to be a “yes” mom as much as possible

Let’s face it. Parenting requires a lot of micromanaging, a lot of times when I have to step in and overrule their preferences and decisions.

Parenting requires a lot of no’s.

“No, you can’t drink the bathwater.”

“No, you can’t jump off the top bunk.”

“No, you can’t swing from the blind cords.”

“No, we can’t have cake for supper.”

At any rate, there are so many instances where I just have to say “no,” because it’s in their best interest. And there are other times when I have to say “no” because of my limitations and chronic illness. So when I can say yes, I want to as much as possible.

Their choice of clothing is an easy yes. In other words, pick your battles. In the scheme of things, it won’t matter that my son wore snow boots with shorts, except to look back and smile at the cuteness of it. Life is too short to make it an issue.

Because I really do believe it’s what’s inside that matters

To be honest, I’ve spent my whole life trying to match up head knowledge with heart knowledge on this one (and this is the same reason I don’t dye my gray hair). But God’s word says:

“The Lord does not see as man sees; for man looks at the outward appearance, but the Lord looks at the heart.”
-1 Samuel 16:7b

I desperately want my boys to grasp this message inside and out—both toward themselves and toward others. I want them to know that the girl whose clothes don’t match or aren’t the right brands is just as important to God as the girl who always looks perfectly put together (and vice versa).

While we encourage neatness and require cleanliness, I want them to know inside and out—that their true worth has nothing to do with their outward appearance, clothing, or possessions.

When I tell them this, but then tell them that their clothes have to look “just so” before they can leave the house…aren’t I sending a mixed message?

A Note about Appropriate Attire

And, before someone says, “I can’t believe you let your boys wear inappropriate/stained/ill-fitting/dirty clothes,” I will add a few notes here.

  • We don’t buy clothing that we deem inappropriate, so that’s not an option for them.
  • We occasionally choose their clothing for a special event, and we have designated “church” clothes that are a bit nicer. They still may not match, but they are collared shirts especially for church.
  • We eventually make them take off a particular clothing item for laundering. Yes, that has come up! They each have shirts they would wear everyday for a week if we would let them, but we don’t.

What about you?  Do you pick out your children’s clothing, or are they likely to be found in completely random mismatched outfits every now and then?


  1. says

    I stumbled upon your blog and what a treat! Your precious children sound just like mine! I have a 3 year old that insists on wearing phants and boots this summer. I feel the same way you do about it. Thank you for sharing and I subscribed to your wonderful blog! Have a nice night :)

    • Crystal says

      lol…so funny with the pants and boots! Thanks for your sweet comment, Barbara and for sharing about your little one as well.

  2. says

    Unless we’re going somewhere important or the outfit chosen is completely inappropriate for the weather, I let my 5 and 3 year olds pick out their own clothes as well. My 3 year old son prefers to dress up with button up shirts and neckties and my 5 year old daughter loves to layer shirts.

  3. says

    Wonderful post, Crystal! I do exactly the same thing. The inappropriate clothes never make it in the house, and I do make sure what they wear to church, etc. is all right, although they can start the decision process if they’re interested. (“I want to wear my beige pants”, etc.) Eventually, they need to develop their own style, and they never will if they don’t get to make any choices. I see that as going along with the self-confidence. My mother made all my clothing decisions for me (and many others as well), and when I was in the position to set up my own household I had no idea what I was doing, what I liked and didn’t like. I’m not a big decorator at all, but I mention that only because our homes need to be comfortable and a reflection of us. I think that all starts with the seemingly little decisions in our childhoods.

    Okay, well, I rambled a bit there, but I hope you can see my point. :) And you make another excellent point about the people who don’t look “all together” being just as important as those who do (spoken as someone who feels like she rarely looks like she is “all together”). I’m gushing now, so I’ll sign off. Thanks for another great post!

    • Crystal says

      Meghan, we can start a club, because I definitely don’t have that put-together look! lol. Also, I completely understand what you say about that confidence starting in childhood with the small decisions. Great point :)

  4. says

    Yup, I totally giggle at some of the outfits my kids come up with, but hey, as long as it’s semi-appropriate clothing (i.e. not shorts in 3 feet of snow), game on. For a good 1.5-2 years, my oldest purposefully wore mismatched socks, and was known as the kid with the mismatched socks around the neighborhood. Whatever, he was dressing himself and I didn’t have to. :D The other day my daughter put on a super busy purple with purple hearts tshirt, paired with a busy blue/white daisy skirt and socks pulled up to her knees. I just *had* to take a photo of it, and she posed like no one’s business. :D

    Oh, and yes, I’m pretty picky about the clothing I buy from consignment or keep from hand-me-downs – usually generic stuff (only characters that have made it in the house are Elmo, Star Trek Lego, Thomas the Tank Engine and Tinkerbell), things that cover my daughters behind (holy smokes, have you seen some of that awful stuff?!) and keep her looking like a little girl and not a working girl so to speak.

    • Crystal says

      Lanna, yes, I have seen that stuff, and I don’t envy mothers of daughters trying to buy modest clothing in a world that is teaching them to “flaunt their stuff” by age 5! It’s a sad world we live in sometimes :(

  5. says

    Too funny! I give you kudo’s for this! I too let my daughter dress herself and it always cracks me up! She loves colors, patterns, and prints and has no desire to have them match :) Remember Punky Brewster? Thats what she reminds me of.

  6. Sarah Bedenkop says

    Thanks for crazy splashing me with this encouragement today. I have grown to love my mix matched boys.

    I hope you don't mind if I splash around a bit to get to know you. This looks like a refreshing place to dip into some serious goodness.

    Also wanted to extend an invite… to share this post (or another fave) to encourage even more moms. We could use it.

    Join the Melody…

    • Crystal says

      Thank you so much for your kindness, Sarah! And for the invitation. I did join your link up today :)

  7. says

    The really fun part is when they grown up and they see photos of themselves as kids. My young adult kids look at pictures of themselves and say “What was I WEARING????” and I respond, “Hey, you picked it out yourself.” Lol!

    They picked out their every day clothes and we set guidelines for them. For example, they were allowed to wear jeans on Sunday but no t-shirts with logos on them. They weren’t allowed to wear shorts and flip flops outside the house in the winter time. I mean, duh!!!!!! But snow on the ground and shorts seemed to be just fine with my kids, lol! Thanks so much for linking up to the “Making Your Home Sing Monday” linky party today! :)

  8. Sarah Mueller says

    I completely agree! I almost never intervene in m boys clothing selections (well, except for the two year old and he doesn't care. My two oldest wear the same clothes to church EVERY week. These are church clothes but it drives me a little nuts. I guess as long as they are neat and presentable, I'm ok with it.

  9. says

    Yep, I generally let my girls pick out their own clothing and it can be an eye opener to see what they think fits their personal style. (they are 9 and 12 now) We don’t buy anything that’s not appropriate, which is not easy if you’ve seen girls’ clothing lately, and we don’t allow them to wear things that aren’t appropriate for the weather – no swimsuits in December, for example. Otherwise, I believe it builds self-confidence and independence to choose what they want to wear. There are so many more important aspects to their lives that have nothing to do with what’s on their bodies – I’d rather concentrate on those things than clothes. Great post!

  10. says

    Thanks for sharing this! I've given up the Battle of the Clothes, and as long as they're clean and in good repair when we go out, we're good. I gave up the Battle of the Hair, too, as my 11 (ALMOST 12 MOM!) year old's purple hair tells the world. ;-) I really loved this post. :)

    • Crystal says

      That’s great! my parents never made hair an issue either. I always had really long hair, while both of my sisters usually had REALLY short hair, and my youngest sister graduated high school with neon orange hair!

  11. says

    Love this! My girl will probably be very similar..considering she demanded (in the way only a 19 month old can) to wear a tutu over her pjs this morning before she got dressed for daycare :)

  12. Sarah says

    I have said YES quite a bit more often. THanks for the gentle nudge and the joy when my youngest adorned himself with bright orange and red today.

    Thanks for joining the melody this week. I would be delighted to have you add your voice each week. I jot some momma notes on Monday … but its a post whenever you can during the week kind of link up. I get the filled to the brim momma schedules.

    Happy day,



  13. says

    I always let both my kids pick their own everyday clothes when they were young but when they started school they had uniforms so neither of us got to pick. Clothes was just one of those things that wasn’t worth battling over.

  14. says

    LOL I really cracked up at the "no you cannot drink your bath water" sentence. LOL LOL Oh dear – I never thought that was something I would have to say…but I have to say it with each bath. Kids! HA!
    Visiting from Proverbs 31 Thursday.

  15. says

    Clicked over from the Hip Homeschool Hop. I have a 5 year old daughter and your reasons are exactly the reasons we let her pick out her own clothes, too. I will occasionally offer weather advice like “you might be cold in that skirt without tights” or “you might be hot with four shirts on since it is summer,” but other than that, the choice is hers. My favorite is when she “matches” the least noticeable color on two items (usually white); it can create some crazy combinations.

    • Crystal says

      Fun stuff! Yes, I do try to make suggestions like that as well. And we have some crazy combinations as well!

  16. says

    I am right with you! As long as we aren’t going to anything special my kids choose their clothes. We have been seen at the library and grocery store in capes, crowns, rain boots with shorts and who knows what else. Thanks for sharing at Mom’s Library; featuring you this week!

    • Crystal says

      Oh, wow, thanks for featuring my post! And, thanks for sharing some of your own experiences as well.

  17. says

    I pick out what clothes they are allowed to have, from there though they are allowed to pick out what they wear, within reason. I say within reason because we live in MI and if it is January I don't allow tank tops or shorts (that I may have forgot to put away for the winter.) Also my two year old is allowed to pick between 2 shirts. I have found at her young age that looking at her full wardrobe can overwhelm her so I let her decide between just a couple things. I pretty much feel the same way about clothing as you do.

  18. says

    This is great! A good reminder of what is important especially for those kids that are returning to school. My son wears his ninja costume 70% of the time and then all kinds of accessories the rest of the time!! Thanks for leaving your link at Magic Moments Monday!

  19. says

    I’m right with you on this one! For the most part they pick their own. For church, they choose from their “Sunday clothes” (dresses or skirts/pants & button down shirts). Now that my oldest has started kindergarten, we have him choose from his pants with pockets (i.e. not sweatpants or exercise shorts), and have him change if he what he has on is dirty/stained, but other than that it’s up to him. My 3-year-old daughter, especially, is so strong-willed that it is just not worth the battle for me. Sometimes her color & pattern combinations are a bit blinding, but really it just makes me smile. Wouldn’t I love a dose of that self-confidence? Yes, yes I would.

  20. Martha Smith says

    As they are getting older, I am gradually giving them more options. My oldest likes to pick out cool shirts, so I’ll pick up complimentary pieces to go with his choices. My second son is my clothes lover. He works his hand-me downs and occasionally requests a new shirt that HE gets to pick out. His pairings are often not what I would pick, but I let it go unless it really clashes like red and orange together. If I do intervene, I try to make it into an art lesson so he understands the reason. My two youngest really don’t care yet.
    My personal style preference is preppy casual. Even though some of their clothes could be considered “dressy,” I have always made sure they fit well so they wouldn’t be uncomfortable. Because I really like the look, I want to make sure they can enjoy it if they want to. I don’t want them to dislike clothes just because they were uncomfortable once.

    • Crystal Brothers says

      That sounds like a very balanced approach, Martha :) And, love that you consider their comfort with their clothing as well!

  21. says

    I have 4 girls and 2 boys. My oldest son, Levi, will ask my opinion as to what he should wear and if what he picks "looks okay". I'm not sure as to why exactly he asks though. If I give my opinion, he does the exCt opposite of wht I say anyway! LOL I have also learned over the years to "pick my battles" wisely. As long as the kids are safe, happy, and healthy AND appropriate…. Who cares!!! And something that drives me INSANE with my daughters is that they NEVER wear matching socks!!!! After speaking with several peers, I realize it's not just my girls, so my OCD self is coming to grips with this!!

  22. says

    My 4 year old picks his own, I just tell him what is appropriate weather wise. He knows on Sunday's he picks from his closet. I have pre-matches outfits for the 2 year old, but he still picks. As he gets older e will have more freedom like his brother, but for now this simplifies things. He only cares about what's on the shirt anyway.

    • Crystal Brothers says

      Yes, we do have “church” clothes so they choose church clothes from those designated as church clothes.

  23. says

    When I nanny for kids, to avoid inevitable inappropriate clothing choices (shorts in freezing cold weather, for example. Some parents say to let them wear the shorts so they learn what's inappropriate on a stormy day, but that's not much of an option when it's a half hour walk to school and then the preschooler and I are going to be gone all morning to a playgroup), I first ask if the girls want a dress or pants, then grab two dresses (or shirts and pants, sometimes even down to the underwear and socks) and ask if they want to wear this or this. That way we both have some say in it.

  24. says

    My children picked out their own clothes, but I folded them in the drawer in matching sets….shirt, pants, socks together. They could wear any set they wanted, but I knew they would always look "put together." They also picked what they wanted to wear the next day before they went to bed. That helped our mornings go smoother. I don't remember ever having to "fight" with my kids about what they wore. They had complete control, but they never changed things (ie: a shirt from this bundle and pants from another.) I think this is an easy way to let them have control.

    Oh, and when the weather changed, they helped me pack up the old clothes to give away and were allowed to shop for new ones (we usually frequented the Purple Heart Thrift Shop and often found clothes with the original tags still on them!)

    • Crystal Brothers says

      It sounds like you found a great compromise to get the “together” look you wanted while still allowing them to choose which outfit to wear. :)

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