20 Pics That Show What Happens When Kids Decide To Dress Themselves

Kids, especially independent ones, love to dress themselves. They get their favorite things and toss them on, like they’re on a mission to have the best or most fun things. A lot of times this results in some seriously hilarious combinations, sometimes to an almost frightening level. They put on too many clothes, layer after layer of them. Almost nothing matches, unless it’s a favorite color then the color may be similar but it’s different hues or winter boots with shorts. They try their best, but it’s almost always a silly, weird, and funny ending. Regardless of the event, a holiday or school, kids dress themselves terribly and think they’re doing as good a job as mommy.

It’s great to let kids have this freedom, though. Not only does it let them explore their creativity, it also shows us what’s important to them. What clothes they deem appropriate and needed. It doesn’t always work, and we usually have to redress them ourselves, but the learning experience is wonderful. Sure, we may have to clean up the mess of rejected clothes or the ones they picked that don’t work that we have to change. But it’s a small price to pay to let them express themselves. And if we don’t have anywhere to go or it’s a playdate or trip to a family member’s home, it doesn’t matter if they want to wear a costume or mismatched clothes. It helps build their self-esteem and lets them know they can help us with these kinds of things too.

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20 Socks are a necessity

Socks don't seem all that important to most adults. They keep our shoes from rubbing on our skin and our shoes from smelling bad. There's nothing more complicated or special about them. But for kids, they love socks. They put them on their feet and hands alike, they put toys in them, they use them for everything and anything they decide is important. Socks are practical pieces of clothing, but to kids, they're an important accessory that doesn't need to match their outfit or sometimes each other. There's nothing quite like helping a kid get a shoe tied and spotting one long white sock up to their knee and one ankle sock with Santa on it! Kids don't consider matching, they just want to have fun!

This little girl, who is quite pleased with herself, has decided to wear a purple headband, too big black framed glasses, yellow tank top, multiple colored bracelets, pink and brown plaid shorts, a few extra clothes just in case- and, of course, knee high socks that are a grey and blue. None of the clothes match, and the long socks definitely don't go with the shorts. But she's happy, pleased with the clothes she picked out, and ready to add layers as she pleases.

19 Dressing up is a prize-winning job

Not only is it fun to dress up, it can be a prize-winning job! This little girl has picked what looks like a dark police hat, a light pink tank top that's way too big, a light purple skirt, and too big white shoes. She also has other layers that aren't easy to see, except a teal article of clothing that's mostly visible from behind. She's accessorized with a red necklace, a white purse, and something that's difficult to tell what it is hanging from the purse. To top it off, she has some kind of badge she's holding up with the photograph, and she holds it like she's won a prize for her wonderful dressing abilities. She's a mess, really, nothing matches. But she's pretty happy with how she's dressed and her won little prize.

It’s important to let them have this little bit of expression and happiness. Clearly the clothes are important to her, she’s happy as possible to be wearing them. The hat could belong to a family member who she looks up to in law enforcement or even security, someone respectable that she wants to be like. The clothes that are too big look like they might belong to mom, someone who is of course very important to every child. Whatever the reasons, she’s happy to be wearing the clothes she picked out herself, and that is rewarding enough for me.

18 Colors only need to kind of match sometimes

Colors are a kid's favorite thing. The more the better, the brighter the prettier! They don't consider matching, they just see colors and want them. This little girl has picked her own matching clothes and didn't forget the rules of using as many colors as possible. Some of parts of the clothes kind of almost match, but for the most part she doesn't match at all. Her monkey beanie has dark pink, green, and blue, and she's added ear muffs that are a different blue and green too. She’s has a small neck scarf that's various colors, a puffy vest with different pinks and greens, a long sleeved shirt that has pink and purple butterflies, her skirt that is white and has red and pink hearts, and purple leggings. She tops the outfit off with red shoes, too! None of it matches but she's smiling, very happy with her clothing choices.

While she doesn’t match, she’s happy. She explored her dresser and found what she wants, put it all on. She might be overdressed for the weather, but she looks adorable as possible with her messy look. We need to be careful with our kids’ safety during summer, but we should let them explore their fashion sense in the safety of a cool house.

17 Eye accessories are always a favorite

Whether they need glasses or not, kids like to wear things on their eyes. Sometimes it’s glasses, sometimes sunglasses. And, sometimes, it’s even goggles. They don’t have to be appropriately timed, they don’t have to match. Kids want them and put them on, happy with their accomplishment. They love to complete their outfits with eye accessories, matching or otherwise. We might want to stop them, keep them from wearing something that doesn’t go with their clothes or outfit. But it’s cute to let them try it out, see what new idea they might have for clothes.

This kid has yellow pants with a blue, red, and white plaid shirt and a white undershirt. Black shoes cover their feet. How do they finish off these clothes? What eye accessories do they have to finish up their outfit? Purple goggles, of course. None of it matches, but they're proud of their choices. While they didn’t pick unnecessary glasses, which could damage their vision, they did pick swimming goggles that, again, don’t go with any of the clothes. It doesn’t match colors, but it also doesn’t match the type of clothes either. But it’s good to let them try it out, at least for a little while, let them have the freedom to explore.

16 Smiles are, always in fashion

Kids are cute, and happy kids are the cutest. Their wide smiles make the entire world light up, makes everyone else want to smile with the contagious expression. They get so happy when they pick their own clothes, whether it's dressing up or it's getting ready to go out somewhere, they enjoy picking their on clothes. The smile makes the outfit entirely perfect! They look so sweet with their smiles, with how happy they get to dress themselves. It makes it important for us as parents to let them try it, at least now and then, let them dress themselves without telling them they're wrong. It's not wrong, it's child fashion. It's their wants and happiness. It might be hard to step back and let them have the reins with it, but it's important to let them have the chance to try it themselves.

For this photo, the little girl has picked an almost matching outfit. She has on a shirt that features pink and purple flowers, and nearly matching purple leggings. Her shoes are both the wrong color purple and too big, way too many and mismatched bracelets too. She also has pearl necklaces, a shoulder shrug in a different color pink, white gloves that are too big, and of course another different purple colored pair of sunglasses. Who needs matching shades of color? Not this happy, joyous little girl! She's all cheeks as she grins to the parent taking her photo, clearly very happy with her outfit choice. And that's the part that matters, that she's happy and enjoying herself as she learns how to get dressed one attempt at a time.

15 Practice makes perfect

We practice their numbers and their letters, we go over words and potty training time and time again. We practice all the important things so they can do better at them, get better, learn how to do them. Dressing should be no different! Make it fun, make it an experience they'll enjoy and remember. Allow them to make mistakes, allow them to mess up and help correct them after. Guide them like you do for anything else, it’s all about learning and growing, just like you do with other educational activities. It can be tough, but the life of a parent usually is.

This little kid opted to go in a peanut outfit for her daily events and adventure. Costumes are fun, and kids don't care what the day or event is, they want to have fun in them. The little kiddo also has a sign no doubt put on by a parent that reads 'Don't judge my mom, I dress myself.' to indicate, again, this is a kid's choice of outfit. They just want to have fun while having to do things for the day. This mom is doing a great job! She’s allowing the kid to wear what they wish, but also wants to avoid judgement for letting it happen. Instead of insisting the kid takes off the costume, they just put a disclaimer so others know.

14 Happiness is more colors


It’s no secret that kids love color. The more colors the better! It applies to everything in their little lives, including clothing. It’s important to them to have lots of colors, making their lives bright and happy. For example, this little girl has four colors already, counting her hair accessory, and appears to be collecting even more! She couldn’t be happier to mix pink, purple, white, and red together for her outfit. It doesn’t anywhere near match in color or style patterns, but that doesn’t matter. She’s not trying to match, she’s trying to have fun and look cute while doing it.

This can be a great learning opportunity though, too. You can teach her what colors are, how to match them together appropriately, and more about patterns and how they interact with each other. Sure, there’s going to be a mess to clean up. She’s taking clothes out of the dresser, probably as many as she can to find the perfect one to add to her outfit. But having to refold and put away those clothes are nothing compared to how much happiness it fills her with to do her own clothes, or how great of a chance this is to teach her how to dress. Instead of getting frustrated if you walk in and see this, you should sit with her and watch how she dresses, what she does to get dressed, what clothes are important to her for the outfit.

13 Accessories are important

Every outfit usually needs an accessory or two to be complete. In kid logic, that means having a ton of accessories to be ready. In this photo, the little girl has three different accessories, not counting her glasses. Gloves, a hat, and what appears to be a poncho. They don’t mismatch terribly, but they also aren’t a set or really matched either. She has on a colorful blue dress, too. The accessories don’t really match the dress, even with all of its colors. Is she concerned over her fashion sense? Does she mind her clothes aren’t exactly matched? Not in the least! She’s happy to be included in the picture and having an adventure with her family. She doesn’t care if she’s a little unmatched or has on a ton of accessories, she’s just happy to wear things she enjoys.

The best thing we can do for kids who want to dress themselves is allow them to have accessories at least. It’s more obvious the kid picked them out than the parent, and they look adorable with their happy little faces lit up from getting to ‘help’ get dressed. It might not match or they might have on a ton of different things, but as long as it’s not a heatstroke danger, let them have fun! They’re only kids once and they’ll soon be older and know better, we’ll only get to enjoy their silliness for a little while. Let them be silly!

12  There’s no need to match

Kids don’t consider matching to be an important thing when getting dressed. As a mother, I always check colors, shades of colors, patterns, too many patterns, and everything under the sun before we head out into public and judgmental gazes. I don’t want people to look down on my kid or think we’re too dumb to match. It’s a silly fear, but one that I have and am careful of. Still, kids don’t have that bias worry yet. They see a shirt and shorts they like, maybe a hat, and toss it on. All different colors and all different shades and patterns, it doesn’t matter to them. They like it and that’s all that matters at the time.

In this photo, the little girl has on a dress with lovely watermelons, but her pants are blue with chevrons on them. The two items don’t match at all, the colors are entirely different, neither have a matching one whatsoever. The shades are different, even in different colors too. And the patterns are all over the place different, nothing similar at all. But they’re clothes she likes, they’re colors she enjoys. Maybe it’s a favorite dress and she remembered her mom likes to put on leggings or shorts under so she can still play or something like that, and tried to do the same. Whatever the reason, she picked these clothes out and is happy to wear them, matching or not.

11 It’s good practice

While the mismatched colors and patterns might drive us crazy, kids don’t care. We shouldn’t be so hard on them to match, especially when dressing themselves is great practice for growing up. In this pic, the kiddo has on a denim button shirt and yellow pants, and has a red hat waiting to be added to the look. None of it matches, none of it makes sense to anyone except them. However, the child is also buttoning their own shirt, without help, and focused on doing a good job. That’s wonderful! They’re practicing doing it on their own, no worries mom, they have it together!

It might be hard to let the kids dress themselves, but having that freedom helps them grow and learn. It allows them to explore something we do every single day, something mundane that we give thought to so we match and look alright, but don’t always bother with too much. Kids don’t know it’s one of the lesser important aspects of life. It’s important to them. And because it’s important to them, they want to do a good job learning how to do it. As they get older, knowing how to dress is important, and they’ll learn how to match and make sense of their clothes. Until then, we should help them get there by allowing them to dress themselves, at least after we pick the clothes if nothing else!

10 They want to show what they love

Kids are funny. They love what they love and dislike what they dislike for reasons that are beyond us. Maybe they explain the reasons, but they don't always make sense in our adult brains. But they have their tastes like anyone else, and they love to show what's important to them. In this photo, the boy has on a striped long sleeved shirt, fairy wings, wrist decorations that could be bracelets or hair things, a wand, a puffy tutu, and ballet shoes. It's important to him, he wants to wear what he likes and what he loves. It doesn't match, not a thing matches at all. He has red, orange, blue, white, pink, rainbow- every color imaginable and none of it the same shade. But he's happy during Christmas, he's enjoying himself and playing pretend.

It can be really hard for us to let them have this freedom. Especially for some if it isn’t conforming to gender expectations. But it’s good for us to let loose and allow them to explore themselves and the way they dress. It’s an expression of who they are or what they like, it lets them open up and enjoy something as simple as clothes. We want them to look their best, especially around holidays, and we want to show off the best features they have. We want to pick colors that look good and outfits that really pop. But kids just want to have fun, they want to share what they love. These two things don’t always meet in the middle, and sometimes it should be us parents who give ground and let them have more freedom of expression.

9 Old costumes are just other clothes

Dressing up in costumes is usually just for Halloween or other similar events. And we usually make sure all of the costume and what's underneath matches. Kids don't care. They love costumes and view them as any other clothing accessory. This kiddo picked a pirate's costume to put on over a long white sleeved shirt- which could match fine. Except they picked maroon pants to go under the black and red costume. They have a matching hat at least, which has been left on the ground, unwanted. But chances are it's not even an event to dress in a costume! That doesn’t matter, it’s another piece of clothing they love and they tossed it on with a happy thought of showing off and reusing the costume like they would any outfit. They see their shirts worn multiple times, the costume must surely be part of that concept!

In truth, costumes are typically worn once and done. It’s almost a waste of money or time if it wasn’t for how happy they are to participate in dressing up. So when our kiddo finds an old costume and puts it on, our first response is no, go change, you can’t wear that, it’s not Halloween anymore. Unless we’re going to some important event, we should let them wear costumes they pick out, at least once in a while. It’s clearly important to them, they found it out and put it on, we should consider their thoughts and feelings before shooting down their outfit choice.

8 No worry about being too hot

Kids don’t really consider weather. If it’s too hot, they fuss until we can fix it for them. We’re they’re providers, we’re the ones in charge, we can fix anything in their little minds. So when they dress themselves they don’t wonder if it’s too hot for ten layers of clothes. Never mind unfolding and tossing around everything, they just think of what they want to wear and put it on, even if they don’t need so many clothes. It makes sense to them, they can recall wearing layers, they know it’s a thing adults do for them- usually just in winter, but they don’t think about that. Weather is just another word they’re learning and ‘too hot’ is a feeling they can express and have it fixed. They don’t consider how clothes take part in that equation.

In this photo, the sweet little girl dressed herself in dark blue shorts which could be part of a jumper outfit. It's hard to tell with her thick jacket covering the top half of her body, really. She also added floral leggings to the mix. Nothing matches. The jacket almost matches the leggings, but the shorts have nothing anchoring it to the outfit. The outfit itself doesn't really go, either. All the layers and different thicknesses of the clothes are way off. But she's happy to wear what makes her happy. Chances are, it’s way too hot for all the layers anyways. But she’s enjoying herself, and that’s what matters.

7 Hats are always important

Most kids love hats. If your kid is one of those children, you can bet at some point they'll add a hat to their outfit, whether or not it matches. You fix their hair, get it ready to go out, and on the head a hat goes. It’s cute they want that little touch of themselves though, they want to express themselves even if it’s just a little thing. It’s cute to see their little faces, happy with getting to pick out a hat even if just for a little time. It can be frustrating to fix their hair nice, get their locks in place, just for them to mess it up with a hat. Especially if it’s a beanie in the middle of summer, it can make us sigh heavy and frown. However, it’s not hard to clean up the loose strands and explain it’s not a time to wear hats right now, or to let them wear it should weather permit.

This photo pictures a lovely little girl with a beanie on. The background shows it's sunny and probably warm, too warm for a beanie. The pink and maroon of the hat don't match the pinks on her shirt, but she looks adorable with her with stray strands peeking out and showing how sweet her little face is.

6  Never enough layers

Layers are nice to have, they can help cover thin clothing or keep you warm on a chilly day. They look nice in general too, layers can really make an outfit. Kids have this same thought process, though to a different extent. More layers are the best, pile them on and enjoy the outfit. Do they match? No. Do they have to? For a kid, of course not. The layers are fun, the clothes are exciting, it doesn’t have to have more than that to it. Fun and exciting are a kids’ way of life. They do silly things, wear silly things, without a second thought to how it might look to someone else. They don’t have that self consciousness pushing them to confirm to a specific standard.

In this picture, the kiddo went with a costume as the main outfit, the only part matching being their tiara. They added a dark and white polka dot headband, colorful necklace and bracelet, a black and yellow jacket with different patterns on it, pink sunglasses, another type of pink phone, and a third kind of pink purse. They look so happy, though. The colors don't match, but their smile lights up the room.

5 Playtime doesn’t have to match

When it comes time to play, it's more about fun than fashion. Kids don't need special outfits to have fun, they don't need to be dressed up when enjoying some down time goofing around. So it's entirely okay and actually should be encouraged to let kids dress themselves when you have nowhere you need to be and it's time to play. Who cares if they match? Let them pick out a top and bottoms, regardless of matching, and set out to have some fun! If they want a neon orange shirt with red patterns with a purple leggings, let them! If they want shorts over the leggings, that's okay! Just let them explore their creativity while you have nothing you need to do, let them have that fun while you're at home watching them play and learn.

The little girl in this picture doesn't match at all, not even a little bit. She has a butterfly patterned dress in different colors, and soft pants that are green with white flowers. It doesn't match, and it doesn't need to. She's playing, she's having fun. She's not in public, she's not at a holiday event, she doesn't have to match or get dressed up! She just needs to have fun, enjoy her time playing, and learn through doing, as most kids do.

4 Costumes aren’t just for Halloween

Again, kids love costumes. Halloween or not, they enjoy dressing up as someone or something they love, playing pretend, saving the world. Sometimes it can be difficult, we want them to wear 'normal' clothes, look appropriate. Sometimes they want to wear a costume five minutes before it's time to leave for school, and changing them causes an entire meltdown. Sometimes, though, we need to compromise a bit, let them have their freedom. Maybe not for a school day, but it doesn't hurt to let a kid dress up in a costume when we go out shopping or have to run errands.

This little boy is quite happy with himself after he put on his Superman costume. Maybe he's getting ready to visit grandma's house, maybe he's on his way to school. Whatever the trip invovled, he felt he needed to be the Man of Steel for it! And it makes him so happy to see his reflection, see his costume in play. We might want to tell him he can't wear it, it's not Halloween, go change. But if it's not some important event or location, why does it matter? Let him be a super hero, let him have his fun!

3 Fuzzy boots in summer is a win

Kids have no concept of something being too hot. Much like the entry about layers, kids just know that if they're too hot, a parent or gardian will fix it. Which is why it is no surprise to know that kids will wear winter boots in any weather! Middle of summer, one of the hottest days so far, and you can bet at least one kid somewhere is trying to get on fuzzy, hot boots to wear. It doesn't make sense to us, but because we're older, we know better. We know that thick booty will make our feet sweat and our body temperature rise, we know it's not a good idea and should pick something else to put on our feet so we're comfortable. But kids just know they like the boots.

The kiddo in this picture is no different. She has on a big black hat, blue sunglasses, a light pink dress, a black purse in one hand and Woody from Toy Story in the other hand; and she tops her outfit off with dark pink, fluffy, furry, winter boots. It's the end of May, it's much too warm for the boots. But she doesn't seem to mind at all, a smile on her face and looking like she's ready to go to town. She's happy, she's pleased with herself. She doesn't match and there's no way she won't get too warm with the boots, but she doesn't give it a second thought as she goes outside to start her day.

2 Wings are also always a favorite fashion

Kids love to wear dress up or costume clothing. A favorite is always wings! Wings are fun, we can't fly and the idea of flying, especially to a child, is a thrilling thought. Plus the wings are usually very cute, sparkly and lace and shaped fun. They are easy to wear and fun to have on, kids can quickly put them on. It's so fun and playful to put on wings, regardless of the outfit. It seems sillier than usual to us to see our kids want to wear wings with any outfit, but it’s still important to let them wear these clothes and accessories. They get to express themselves and what’s important to them, including a pair of wings

The kiddo in this picture has on wings that are white with a more dense white decoration on them. She Also has on a paper elf hat that's green, a blue Spiderman shirt, a long sleeved grey shirt under it, a pair of light denim pants, Batman slippers, and a red necklace. The only thing that matches is her white sunglasses and lovely smile. She's happy to have her outfit on and to have added the wings, clearly quite proud of her clothing choices.

1 It’s supposed to be fun!

The little boy in this last photo is having a blast. He's making a silly face with his yellow and blue car shirt, and with his bare little legs and feet it's safe to guess he's in shorts. It's hard to tell with the brightly colored rainbow tutu he has on, no doubt added because it's beautiful and fun. He's having a lot of fun dressing up, and that's the most important thing to it. Regardless of him being able to dress himself, an important skill to have, he's also enjoying himself too. It's wonderful to let them learn how to dress themselves, it's an important experience to have and to learn. It's also important to let them learn how to match, with us guiding them gently to things that make sense for an outfit.

Those are all important reasons to let kids dress themselves, but happiness and joy are the most important. Letting them have the fun of exploring clothes and silly accessories is a very important part of dressing up. Their happy, smiling faces make it worth the folding of clothes later. The fun they have is so, so very important too. Fun is how kids learn best, how they can do their very best. Let them have fun, let them enjoy themselves!

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