First-Day-of-School Clothes

Henry and I had a difference of opinion about his First Day of School outfit. My opinion was that the outfit should be one of his nicer ones: it didn’t have to include a vest and bow-tie, but maybe a solid-color polo shirt, for example, or a patterned button-down—but not a character t-shirt. Basically the same as a School Picture Day outfit. When I had to think out WHY this was my inclination, I came up with four reasons:

1. That’s what I remember from my own youth
2. The first day of school is Special, and we dress up a little for Special
3. Making a good first impression on the teacher
4. Looks nice in the photos I take at the bus stop and post on Facebook

 

Henry’s opinion was that the outfit should be one that expressed his interests. That is, he had the Exact Opposite idea: I was saying “collar shirt—or maybe even a solid-color t-shirt but definitely not a character t-shirt” and he was saying “definitely a character t-shirt, and the only question is WHICH character t-shirt.” When he had to think out WHY this was his inclination, he came up with two reasons:

1. Making a good first impression on his classmates
2. Communicating his interests to other children quickly and easily

 

I could have pulled “No, most days you can wear what you want, but I am the boss and we’re doing it my way for this one day” (this is what I do on Picture Day and Easter and Thanksgiving and Christmas and certain other occasions, if necessary), but we did it his way, because I could see his point. Also because he was quite nervous about the first day, and I thought a favorite shirt might help. Minecraft t-shirt it is.

When I was helping Edward pick out an outfit, then, I explained Henry’s philosophy and asked if Edward subscribed to the same one. I showed him the solid green polo shirt I would pick for him if it were up to me, and asked if instead he would like to choose something more like what he’d normally wear—more representative of his personality and interests. He said, “Yes, but, that shirt looks NORMAL to me.” Green polo shirt it is.

I wasn’t going to plan out Elizabeth’s outfit with her, because she has been highly opinionated about her clothes since infancy. But when I saw she had set aside velour pants, I suggested she might want something less warm in her non-air-conditioned classroom.

Rob is in 10th grade this year and William in 8th, so they’re on their own for clothing choices. I would say something if I thought their choices weren’t quite right—like, if they were wearing something stained or too small. But I don’t try to make them wear shirts with collars or anything like that.

 

I’m interested to know how you do things at your house with first-day-of-school outfits.

60 thoughts on “First-Day-of-School Clothes

  1. Rachel

    One first grade boy here, and we had the exact same issue. I thought he should dress it up a bit (we call it church clothes) and he thought he emphatically should not. My main reasoning is facebook photos. He first came downstairs in basketball shorts and a soccer jersey. I reminded him that we don’t wear exercise gear to school and “helpfully” suggested a nice polo shirt. He came back down in camo shorts and a new superhero t-shirt. Done and done.

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  2. Lynn

    Ours are in Grade 2, 5, and 6, and they’re basically on their own. I remember dressing up for school photos each year, then being disappointed when only the shoulders-up part of my outfit was in the photo. Around grade 10 I started wearing just my usual t-shirt and jeans to photo day, and was much happier with the pictures – no scratchy outfit, looks more like me, I look more relaxed, etc.

    So now the kids are free to choose what they want except for things like weddings. Usually this means plain t-shirt and shorts for my son (grade 6), totally unmatched shield-your-eyes mixture of patterns (chosen for comfort, not style) by my middle daughter, and the world’s fanciest poofiest dress for my youngest.

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  3. KateB

    Church clothes (aka polo shirt, nice shorts, solid color T, etc.) are required for first day and picture day. The rest of the year, they can choose. I have 4th and 1st grade boys and they don’t care enough about fashion to complain. I did let them wear those STUPID looking sports knee socks, though, so they were thrilled with that. I do have a set of rules hung up in the closets, though. (No navy blue and black, No dressy top with sporty bottoms, No brown with black, etc.) Just basic rules so they don’t look like goons.

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  4. Catherine

    Our school has a “dress code” that amounts to a uniform (solid collared shirts and solid pants/shorts for boys), so it’s less of a question for us, but our 2nd-grader chose a t-shirt with the school logo (also allowed) for the first day, instead of the usual polo shirt. I will admit that my first instinct was to ask him to change into something “nicer,” but then I thought again and realized it was probably okay — and this way, the “first day of school” picture proudly displays his school’s name and logo. And then at drop-off, it turned out that a lot of other kids (parents?) had made the same choice, so that was cool.

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  5. jen

    For Kindergarten last year, I think I helped him pick out a shirt and it was a polo type shirt. This year he insisted on some random t-shirt that I think was even stained but he didn’t care and it was what he wanted to wear so we went with it. I think I made him change his shorts because he was wearing a navy shirt with black mesh shorts at first but that was the extent of my exerting authority over the process. On a daily basis, he dresses himself and I make small suggestions when I can but I try not to say too much because I don’t want him to be worried/fretting about his clothing. He’s the type of kid that latches on to ideas and takes them to the nth degree and I don’t want to start something.

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  6. Purdy bird

    First grader has a uniform but I made him wear a “nicer outfit” when we went for orientation (collard shirt, nicer shorts) for the same reasons you gave. I did wonder if he’d feel more comfortable if he chose his clothes so I made a last minute offer for him to choose a different shirt, he said yes and then decided it was too much effort so he wore what I chose. PreK girl happily wore the dress I picked out but is holding fast to her “no touching my hair” policy so no fun first day braids or pigtails.

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  7. Rayne of Terror

    I let them wear what they want, but I help as far as making sure it isn’t stained or too small. One wore a character shirt, the other wore a plain tank top, they both wore as much neon yellow as possible.

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    1. Rayne of Terror

      The too small comes into play because my 5 year old and 9 year old have the same waist size and share a room so too often the 9 year old wears the 5 year old’s shorts and doesn’t realize they are WAY shorter than current boys fashion. It’s a struggle finding long enough shorts with a small enough waist for a 5 ft tall 75 lb 9 year old.

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        1. Rayne of Terror

          The best pants I’ve found for my 9 year old son are the Lands End school uniform girls piped athletic pants. The girls pants have a waist that is 2 inches smaller than the identical boys pants, and there is no indication on the tag whether the pants are girls or boys. I wait for them to go on sale for $14.99 and stack a 30% or 40% coupon and buy them 4 or 5 at a time. My only complaint about them is they wear at the knees in about 3-4 months.

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  8. StephLove

    I have always picked the kids’ first-day-of-school outfits (or given them a choice of a few) when they’re in elementary school, which means I am doing it for my daughter but not for my son. I do try to pick something she likes, so she only grumbles a little. I am still picking school picture day outfits for the 8th grader (which is today coincidentally) but I was thinking in high school next year I’d cut him loose and see what he wears.

    Up until the spring of first grade, I was picking one outfit a week for my daughter, mainly to make sure her brother’s hand-me-downs got some use, but I had to give that up. She really didn’t like it.

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  9. chris

    My husband took each child individually on a special “first day of school shopping trip”. My least favorite thing about this is my husband is color blind. Luckily, he is not above asking a store employee for help to make sure the 8 year old isn’t telling him things match just because it is what he wants. Said 8 year old ended up with a black Darth Vader t-shirt and black shorts for the first day. His 11 year old sister picked out a pair of light grey leggings and black t-shirt that had a unicorn with a candy corn horn and jack-o-lantern on it. They were very proud of themselves because the shirt is so totally her, but I gently mentioned this was a Halloween shirt and was she sure she wanted to wear it 2 full months before Halloween? She was sure and I am pretty sure she will wear it year round unless some jerk at middle school makes fun of her. Both looked presentable and got several compliments on their cool shirts on FB.

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  10. Amanda

    I used to worry about what my kids wore on any day of school especially the first because I remember that being a MAJOR thing when I was a kid. But my kids haven’t made it a thing and I got to the point of remembering that I didn’t enjoy that it was a major thing (everyone showing off their best outfit) and that they should choose what they wore based on school guidelines.

    I also used to worry that my children tossed my own adorable ideas for the scruffy look but then I was at school many a time and there weren’t many children dressed to the point of adorable. They were mostly dressed for comfort (every kid has PE every day) and their own sense of style.

    I think if your kid knows what sort of outer armor is going to make them feel best on the first or any other day of school, let them roll with it (as far as school rules and not-looking-like-a-hobo allow).

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  11. juliloquy

    I love that you asked Henry about his motivations. Very informative. I am impressed at his ability to communicate his preferences. It was supportive of you to let him do his thing in light of that.

    My (1st grade) daughter’s first choice was a spaghetti-strap tie-dyed dress, but I reminded her that straps have to be two fingers wide for school and that she could wear a shirt underneath the dress if she liked. She changed into a short-sleeved dress, but then my husband noticed that she has PE on Mondays. She changed into shorts and a striped t-shirt.

    My (4th grade) son chooses whichever t-shirt/polo is on top (in this case it was a 4H shirt) and khaki shorts. I have to remember to mix up the clothes in his pile, otherwise he’ll wear the same thing more than once in a week.

    I tend not to intervene, although I usually remind them of picture day so they are mindful of their choice for that day.

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  12. Lawyerish

    I laughed about Elizabeth having strong opinions about clothing “since infancy” because that is also how my child is. Our first day of school is next week (she’ll be in her last year of preschool), and I predict that she is going to want to wear one of her fanciest dresses, which means I will have to talk her down into something she can play in/get paint on. Lately she is obsessed with wearing “long dresses and NO pants” (meaning leggings or even shorts underneath). Since she is super tall, this is a challenge. I did buy her a new navy jumper, which is what she chose for the first day of school last year, and I think she has that in mind which I am fine with. Then she’ll want to wear her sparkliest dressy shoes, and fine — I will let her for the first day, and then it’s back to comfier (yet still sparkly) Mary Janes and sneakers.

    I love little girls’ clothes so much, but I do hope that in the end she will go to a school that has uniforms for kindergarten and up. It would make our lives so much easier (and she already loves jumpers and skirts, anyway).

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  13. Elizabeth

    Last year when my daughter started kindergarten, she was VERY into wearing dresses, to the exclusion of all other types of clothes. So I was thrilled to snag a Diane Von Furstenberg for Gap wrap dress in her size on super clearance…it was adorable, smart, special without being dressy, and a perfect mix of her style and my taste. This year, for first grade, I found a panda-themed dress with a matching headband, which I thought was perfect because her school’s mascot is a panda. But over the summer she went off dresses! So she chose her school t-shirt and a denim skort for the first day, which I allowed because she was showing school spirit and it was neat and cute. I tried to get her to accessorize with the panda headband but she didn’t go for that. Who knows if the panda dress will ever see the light of day. Same goes for the second-hand Lilly Pulitzer sundresses I stockpiled pre-summer.

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  14. Jenny Grace

    I have some rules about school clothes: no sweats, no gym/basketball shorts, no stains, no holes in the knees, no wearing the same thing multiple days in a row (Gabriel gets stuck on favorite pants and ONLY THOSE PANTS WILL DO NOT THESE OTHER PANTS THAT ARE LITERALLY THE SAME IDENTICAL PANTS).
    But. No special extra rules for first day of school. I do try to get a button down shirt for picture day.
    And I try to make sure that he looks generally presentable.

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  15. Becky

    I choose the first day clothes for my second grader. So far he has worn khaki shorts and a striped polo (different colors each year) because I am that kind of mom that likes to make a good first impression and have a nice first day photo. It helps that he never even notices what he is wearing, so he doesn’t care. It really doesn’t make sense when I think about it because 1. I teach at his school and so every single staff member knows him so there is no first impression. and 2. He wears regular stuff – t-shirts and athletic shorts or jeans the rest of the year.
    In my third grade class I take pictures on the first day and they are up on a wall for the rest of the year. I would estimate that 90% of the girls and 50% of the boys are wearing nicer-than -usual clothes on the first day.

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  16. allstarme

    I do prefer Elliot look slightly nicer on day one but day to day, he is different about whether he is open to accepting my opinion. This year I let him just pick whatever and he ended up in black basketball shorts and his favorite tech shirt, which is bright orange. He absolutely loves this outfit and I had to let that go. It made him feel more comfortable on a day when he’s already super nervous, so I guess it worked.

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  17. ESL

    I have two 3rd graders. In the past the only things I have really considered are first impression on the teacher, and first day of school photos (mine, not the school’s).

    My daughter wanted to wear a homemade tie dye which looked… homemade. I suggested that for day 2 and a dress for day 1 and she agreed.

    My son doesn’t care or even notice what he’s wearing as long as it’s comfortable. In the past I’ve always gone collared shirt on first day of school for him. But this year I started thinking abut the impression on his classmates too, so I went with a nice t-shirt with a nice/subdued bicycle graphic.

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  18. Peyton

    All of our local schools are uniform only, so I spent most of the summer reminding my daughter (PK4) that we didn’t get to pick the school clothes, the school picked the clothes, and if she wanted to, as soon as she got home she could change into anything she wanted, but she always had to wear the same school clothes, etc, ad nauseum. And she was totally fine with that. Until we went to the uniform store, which supplies a lot of local schools, and she decided she wanted the uniform for a different school than she was attending. OMG, the screaming fit that was had! Sigh. But she’s been handling it very well ever since then. She’s actually pretty excited to get ready every day.

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  19. Kami

    My third grade daughter & I together pick out an outfit before bedtime. Thank goodness we (95% of the time) completely agree. My husband can confirm we both love clothes/shopping a lot! She’s pretty laid back and seems to value my opinion, so far….she’s also very easy going about any hair style as long as it’s “cute”. She told me a couple of days ago a little girl liked her braid and she had to feel the back of her hair because she wasn’t aware I had put one in…lol!

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  20. sarah

    My oldest is in 1st grade and while I am the one choosing the outfits every night before school and he rarely has an opinion about clothes, I can bet that if I had laid out a collared shirt, he would have fought me on that. Also, I didn’t notice any particularly dressed up children in the drop-off line so I suspect that he would have been over dressed in a collared shirt for his school. Also, I have always told my kids that character shirts are “sleep” shirts and athletic shorts are “sleep” shorts and we thus are able to avoid any differences of opinion on what I would want them to wear and what they want to wear. Plus, my three don’t seem to be all that opinionated about clothes. Opinionated about plenty else! Or maybe we just share taste, haha. I shop a large consignment sale twice a year for the kids and find great second hand Gap Kids stuff and I make a big deal of going through it with each of the kids to show them what I picked out and they seem to get really excited and will gladly wear any of it. But as they get older, I know that will change as they see their peers wearing certain things. Also, uniforms. Please let’s just do the uniform thing, schools

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  21. Missy

    We have 3 kids in uniforms so no first day of school clothes decisions here. I do tend to make sure the kids are wearing new uniforms the first day vs. hand-me-downs/saved from last year clothes. It just doesn’t feel like the first day of school without crisp clean new clothes and shoes! Picture day is a week before school starts so that is where we are choosing outfits. They generally get a new special outfit for that since they only have uniforms for school. I have always dressed the boys in collared shirts for pictures so that is what they pick out.

    One year my daughter wore a super cute dress for pictures that had skinny straps. Her hair was long and covered the straps and the way the picture was cropped you couldn’t see any of the dress. She looked naked! So that is our only rule for her – no straps. We laugh about it every year!

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  22. nonsoccermom

    No super special guidelines really, but I do make sure they’re wearing new clothes at least. We always wore something brand-new and extra-nice (usually a dress) for the first day when I was growing up, so I have that in the back of my mind. Plus if the clothes are new, I don’t have to do a double-check for stains or rips.

    My daughter (1st grade) is easier to “dress up” and more amenable to it than her brother, who is in 6th this year. But I actually talked him into wearing jeans (his first pair) so I’m counting it a win. He won’t wear polo shirts or anything like that without a big fuss, so I’ll take what I can get…his preference would be athletic pants, a t-shirt and a hoodie. Sigh.

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  23. yasmara

    If I didn’t let my 7 year old wear athletic shorts & a character t-shirt, he would probably try to go naked. It’s a battle I decided wasn’t worth fighting, especially in the morning before school. I will make him wear pants once the weather dictates it (at least in my mind – he would still be wearing shorts when the high is 40F). This year he chose a camo patterned shirt with a skull and crossbones motif. When asked if he just took a shirt from his drawer or picked that one on purpose, he said he picked that one because he wanted everyone to know he likes pirates. So, ok then. I probably cared a lot more for Kid #1, but he only started actually caring about his clothes in the last 2 years (3rd grade/4th grade), so it barely mattered with him. Kid #2 has had clothing opinions since he was a toddler!

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  24. Elisabeth

    My kindergartener wears whatever is on top of his dresser drawer. I manipulated the top of the dresser drawer so it was a polo shirt and nicer shorts for the first day and I will do it again for picture day :) The only clothes he really has opinions on are his pajamas. He loves them and wants to wear them always, so the rule is that he can only change into them if he has checked with me first and we won’t be going anywhere else that day.

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  25. Stacey

    For kindergarten & 1st grade I limited their choices to one of 3 new outfits. After that I limit myself to interfering only when the clothes are dirty/too small or clash horribly. They are about to start 5th & 6th grade. My oldest will wear the same shirt 3 days in a row and my youngest’s favorite shorts are red/black/white plaid. He likes to wear them with a neon yellow or dark blue shirt. I’m always intervening with those shorts. Even if all we are doing is going to Wal Mart.

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  26. Shawna

    I pick the kids’ clothes with them for first day since we’ll be doing pictures and I want them to make a good first impression on their classmates and new teacher, but that takes into account their tastes and my daughter is definitely not a girly girl. In fact, for the last few years the rule has been that she has to make use of the slightly nicer clothes M-Th, and can wear her oversized boy clothes mostly on Fridays. I relax that after the first half of the year, but I never let it go completely because when she gets older and chooses something I consider completely inappropriate for school, I won’t have surrendered all the decision-making to her and have to overcome a history of not interfering. (My sister became a teenager with a taste for skin-tight red leopard-print leggings and low-cut tops and my mother just silently hated the outfits but never said a word about it. I think my sister’s reputation and experience in high school suffered for it.)

    I’d love it if people chimed in on this question though: my kids (now 6 and 8) often dye a permanent patch or streak into their hair at daycare (which is run by a woman with bright blue hair herself). They want to know if it’s okay to do it this week, which is the week before school starts. I have zero issues with my daughter doing it, and any other time I’d be fine with my son doing it, but I’ve suggested to my husband that maybe not for the first day of school for my son. What do you think? If you’d let them any other time, would you think the beginning of school is different because it’s the first impression for the school year? Or am I overthinking it and other first graders would just think it’s cool?

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    1. Carrie

      Shawna – I have to admit that my instinct is the same as yours in that I think it would be totally fine for your daughter but not so much for your son. I would worry that it comes across as “punk” to a teacher when its on a boy, even though I know it is ridiculous and sexist. I say to trust your gut and have him go to the first week of school clean-cut and he can bust out the hair streaks on week 2.

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      1. Shawna

        I appreciate the validation Carrie, and glad to know it’s not just me. I’m not sure a 6-year-old would come across as “punk”, but it’s definitely less common for boys to have colourful hair. My daughter always gets a ton of compliments on her hair streaks (green historically, but now blue), and people ask where I got it done.

        In the end, my son decided on his own to do it another time. I’m relieved because in the past he’s sometimes sported something different to school (a pumpkin hat, nail polish, etc.) that he was excited about, then ended up being teased and came home unhappy. I want his first week of school to be positive and him to make the first impression, not his hair.

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        1. Shawna

          Update: First day of school was today and probably a quarter of the girls in my daughter’s class had a coloured streak in their hair. Win!

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  27. Jane in Pa

    For my boys (2nd and 3rd grade), our elementary school has uniforms so there isn’t a battle to be had. BUT, I do use nice, new clothes rather than “stuff from last year that still fits”. My daughter goes back to preschool in a couple weeks and I am certain she will want input….maybe I should have her choose 2 options now to avoid haggling later ;)

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  28. dayman

    My oldest is in kindergarten and generally happy to let me choose her clothes, so I did, with the same in mind (good impression on teacher, good pictures, and also, i think it shows a certain respect for the start of the school year? or something? I can’t explain it well.) My middle child started insisting on choosing her own clothes the minute she turned two, so that will be interesting. We are one of the only schools in our district that doesn’t require uniforms, and I’m a little disappointed because that certainly would have made life much easier. My husband grew up going to Catholic school and still feels strongly about dressing nicely- he never, ever wears work out clothes unless he is working out, he will change into a clean t shirt to go to the grocery store, etc. I am generally a sloppy mess, and I wish I were a little better about that, so I see school clothes as a chance to instill that….but I also know I am sloppy because I cannot STAND uncomfortable clothes, so yoga pants and t shirts it is, and it seems kind of mean to force my kids to be uncomfortable while I’m happy as a clam. I also think they can concentrate more if they aren’t distracted by an itchy sweater or a tight waistband.

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  29. rebecca

    Henry is absolutely right. My son came home talking about how many kids in class had Lego shirts on and how they counted and identified the Lego movie vs non Lego movie Lego shirts. The whole class chimed in. Very glad I let him wear what he wanted, as long as it was not stained or had holes.

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  30. Kara

    Our school has uniforms and I love them more than life itself. The older two girls light light blue shirts, the youngest likes navy. I buy everything in duplicates from Old Navy during the uniform sales. So for first day of school, I only ask that they wear one of the nicer uniform shirts, not one that was clearly used in art class last year.

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  31. Jody

    My kids are in eighth grade now, and it’s interesting because my daughters have swung around to caring A LOT about what outfits they wear on those days, and they want those outfits to be slightly fancier than what they wear day-to-day. My son wears nothing but polo shirts and jeans to school, it’s his thing, so I pick up a few new ones and throw away a few ratty ones and we’re done. Meanwhile, the girls did military-planning level shopping trips to the Mall to get ready.

    BUT, there was a period of three years when one daughter wanted to wear her favorite shirt on the first day of school and it was the SAME favorite shirt, and I really wanted her to wear something fancier AND different, because of the first-day-of-school photos, but each year, I talked myself off that ledge. This daughter was/is stressed before the first day of school, and getting something “that looks nice” for a ten-second photo turns out to be less important to me than letting her be comfortable in her own skin/clothes. And now, when I look at those photos, it turns out that I CAN tell which year is which even though she’s wearing the same shirt, AND I think it’s adorable that she picked that outfit, which none of us will ever forget.

    So, I shook off what I totally admit was a childhood hangup about first-day-of-school outfits. Also, I KNOW that this was a childhood hangup, because during one of those “every year, the same shirt” years, I hadn’t really done much new-clothes shopping by the first day of school — we live in NC and it will still be hot for a month and the kids are going to be wearing their shorts anyway and the longer I wait to purchase pants, the less likely they are to outgrow them in March when everyone will inexplicably be stocking nothing but shorts. Anyway, this somehow came up with my mother and she was HORRIFIED. It was not a new year at school if sufficient numbers of new school clothes had been purchased. I might as well have been telling her we’d decided to skip putting up a Christmas tree that year. It took me a long time to shake that off.

    OTOH, I DO still have this hangup about new shoes. My kids were perfectly ready to wear their grubby old sneakers on the first day, because hey, their feet hadn’t grown and they wanted to do other things with their free time last week, but I really wanted/needed them to have new shoes. So we went shopping on Sunday night, about 14 hours before the bell rang on the first day of school. And I was very grateful to all three of them for indulging me.

    Reply
    1. Rbelle

      My MIL bought my preschooler half a dozen “back to school” shirts. I didn’t have the heart to tell her that not only does my daughter still fit in everything she wore last year, anything she wears to school will get paint all over it that might never come out. MIL seemed really hung up on the “clothes for school” thing this year.

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  32. Emily

    The week before school I sorted the boys clothes into “school clothes” and “play clothes”. For first day I insisted on a collar. Both boys chose polos with a chest stripe and plaid shorts. K and 2nd.

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  33. Devan

    I let them pick, but steered them towards nicer shorts with collars and away from t-shirts. They both wore t-shirts after all, but they did look nice.

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  34. Meredith K A

    I *love* that you reasoned it out with him, had him reason it out from his side, and then decided to let him do it his way since he had good reasons! What a great, empowering relationship. Go you!

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  35. april

    We’re uniforms, but S hasn’t changed sizes since last year so I couple new polos and a couple new khaki shorts and he wore the new-same-as-the-old clothing.

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  36. Kelley

    I wore a nice first day outfit all the way up through grad school! In my younger years (K-3 especially) I remember this being a point of contention with my mom, as I was a bit of a tom boy and she would want me to wear a dress (I think she actually would have been ok with dressier pants, but I didn’t really like those either). From 4-6 I think I just resigned myself to the fact that I had to wear nicer clothes on the first day and picture day (usually the same outfit), and from 7th on I cared enough about style that I enjoyed and embraced the tradition. I seem to recall it was usually a NEW outfit, purchased specifically for the occasion, and I did get to have input on what was purchased as long as it was dressier. So any arguments occurred and were resolved before the night before the first day of school :)

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  37. Erin

    Okay, I must be a negligent mom, because “making a good first impression on the teacher” seriously never occurred to me. I am totally fine with whatever my kids pick to wear, as long as it’s not too small or stained/ripped. My 11-y.o. son wears athletic shorts every single day, practically. (We live in SoCal.) He loves geeky kinds of t-shirts that say things like: Never trust an atom — they make up everything. And sure enough he wore one of his t-shirts and athletic shorts. (It also has never occurred to me that he shouldn’t wear athletic shorts to school!)

    My daughter likes to dress up and spent a lot of time planning her outfit and accessories.

    I want my kids to feel comfortable with their own style. It gives each of them confidence to choose clothing that reflects who they are, and I’m fine with that.

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  38. Laura

    Our kids wear uniforms, so it is never an issue. They get 4 or 5 dress down days a year and then they can choose whatever they want (provided that it is not offensive or revealing).

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  39. Julia

    when my son (21) was in kindergarten, the teacher reminded them that the next day was picture day and they should “dress up”. He was sure that meant to wear a costume and would not be swayed. He went to school dressed as Daniel Boone, with a vest and coonskin hat. He never noticed that no one else wore a costume. It’s still my favorite school picture of all time.

    Reply
  40. Joanne

    My kids wear uniforms – well, two out of five of mine wear uniforms this year. My oldest just started going to public school after five years at an ABA therapy center (he has autism), but I never think about what he wears except from a useful perspective. Like I think how easy are these pants to get up/down, etc. My three year old is in preschool and I never think about what she wears because she, like Elizabeth, has big opinions about it. My six and five year old are the uniform wearers and I have been dressing them alike (same colored collared shirts) and it’s SUPER fun for me, I think they look so cute. I also like to do their hair in a cute way on the first day, so their teachers will think they have the kind of mother who braids hair, etc., in the morning. That way I figure maybe they will sustain that belief even later in the year, when I forget to even tell them to brush it, ha!

    Reply
  41. magpie

    I am slacker mom about clothes – as long as it’s clean and hole-free and fits, anything goes. My 10yo has been begging me to let her dye her hair – her whole head, not just a streak – for the first day of school. She wants to make an impression on her peers. I’m very on the fence. It’s hair dye, it’ll wash out. OTOH, well, I don’t think so.

    Reply
  42. SalGal

    First – I’m totally on board with your reasoning but, I’ve more or less given up for the same reasons you gave in this year. My daughter (4th grade) chose a nice dressy outfit and my son (2nd grade) wore a new Transformers tshirt and basketball shorts. I guess even if he doesn’t look “nice”, he looks like . . . himself.

    Funny clothes story about The Boy: We were discussing buying him something to wear to his cousin’s wedding in a few weeks and his reply was, “I’m going to wear a tuxedo”. Thinking he was confused about another cousin’s wedding next year (he’s going to be a ring bearer), I said, “No, not Craig’s wedding. Ryan’s wedding”. His reply? “Yeah, I know.” Sorry, kid. NOT buying you a tux. You get cheap khakis you’ll wear once and a polo you’ll probably also wear for school pictures!

    Reply
    1. Shawna

      Too bad he’d outgrow the ring-bearer tux if you bought it now! How often do you get to use those more than once on a child?

      Reply
  43. Melissa H

    I thought I cared about this but now daughter is in fourth grade and it turns out I don’t care. I did veto too short shorts (against school rules anyway) and something that was stained for the first day but otherwise she was on her own. I’ve sort of given up on picture day as well. School photos are always SO BAD I can’t seem to care much. I just draw the picture day line at something with a big logo/image that would look bad in the class photo.

    Reply
  44. Rbelle

    My elder is only in preschool. I had grand intentions to take a picture for comparison to the last day of school, as some of the other moms do. Turns out, I am not that mom. Not only is my daughter starting to form opinions about what she wants to wear, and they’re not always in agreement with what I would have her wear, the likelihood that I’ll get her to wear the same outfit nine months from now is slim to none. So we went with whatever. Her hair was done better than usual, I call it a win.

    My mom used to sew us an outfit that was to be worn on the first day of school, and for school pictures. I don’t sew, but I don’t plan on asking that of my kids in any form. It was a really neat thing for my mother to do, but every year I’d pick my outfit based on the cool-looking child-model in the pattern book and their cool fabric, which of course wasn’t actually fabric you could get at the store. And every year starting with third grade I would be disappointed by how my outfit turned out, and inevitably go to school feeling unhappy that I wasn’t wearing clothes like anybody else was wearing (in particular, everybody tended to look way less dressed up than me). My kids will already likely have some restrictions on clothing that some of their peers don’t have (whatever the brand name is when they’re in grade school, they’re not likely to get it unless it comes from Target or is on clearance). I feel like letting them choose what to wear the first day they have to make a new impression is the least I can do as long as it’s not inappropriate or grubby.

    Reply
  45. Carrie

    Yasmara and I have the same type of kid in that getting my 6 year old to wear ANY clothes is a battle, so as long as it’s clean, and weather appropriate I am fine with it. I gave up the battle on collared shirts or non-stretchy pants years ago. My 8 year old will typically wear anything I put out for him but has been becoming more and more aware of what his peers are wearing so I try to let him choose clothes that make him feel good, as long as they match. I was actually thrilled this summer when they both really liked the Dri-Fit Nike shirts and shorts in bright colors. It’s like an ACTUAL COORDINATED OUTFIT!

    My only rule for the first day of school is that they wear one of their new outfits and this year they seemed to fit right in with what the other kids were wearing at the bus stop (they weren’t the best dressed, but definitely weren’t the worst). I do think what kids wear the first days of school makes at least a small impression on the teachers about me as a parent and our family in general. I have to admit I’m happy that my boys are wearing something other than $5 Minecraft t-shirts from Target this year.

    Reply
  46. Laura D

    We go to a uniform school, so it’s not an issue. Our main concerns are that it 1) fits the uniform code 2) fits and 3) is clean. Grace is a six year old fashionista, so the fact that she has clothes that are just for school is something of a relief. Her first day outfit was just culled from the collection of uniform clothing and we let her choose because her choices are limited, anyway!

    Reply
  47. Monique

    We have SSA – Standard School Attire. District wide it’s navy, black or khaki bottoms (shorts, skirts, pants) and collared solid colored blue or white shirts. Each school can choose more colors. Boy Kindergartener’s school says any color is fine, so I put a complete outfit in each bin of a six bin thing I have, being sure that navy and black and orange and blue don’t end up in the same bin. No navy/black, because. No orange/blue because they’re my anti-team color. I’m from Alabama, and a Bama fan, so no Auburn colors if I can help it! I know it’s silly, but it’s what I do. First day he wore the only pair of shorts I was able to find in all of Nashville, khaki, and a bight blue top. We have sales tax free weekend the first weekend of August and ALLLLL the shorts in all the stores were purchased. I have since gotten him several more shorts, so he’s good for now. Girl High School Junior is very creative within her boundaries. Her school only allows orange, blue or white shirts – school colors. I know. I am aghast. But she doesn’t like orange and they allow any shade of orange and blue, so we go with peach. Not Auburn orange, so works for me. She wore a new black skirt and peach tank top with an existing white collared shirt. Boy doesn’t care what he wears, girl does as she likes. I only point out if something is too hot/cold for the day, or if she’s showing too much cleavage or leg. She doesn’t usually do either on purpose, but also doesn’t always notice.

    Reply
  48. Farrell

    My daughter is like Elizabeth- super picky about the feel and comfort of clothes.
    She threw on a tank and shorts, though I did straighten her hair (it’s naturally wavy), but basically she looked the same as every other day this summer. Works for me as fashion is just not my thing.

    Reply

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