What Not to Wear: To your Child’s School

In case you all have ever wondered, I have some of the best friends in the whole world. We chat about everything under the sun, nothing is off limits, and everyone supports each other. I am super excited to share with you all a post written by Diana Winchester, one of my best friends. She is a teacher and has some first hand advice on what not to wear to your child’s school. I hope it gives you all a laugh and some self confidence in yourself as well.

If you are reading this, I trust you either know Sarah, or have read her other blog posts.  You know she has amazing style. Even on her worst days she could put Blake Lively’s Red Carpet looks to shame.  Sarah and I have an ongoing group chat with a couple other friends of ours. We all have little one around the same age, so we trade mommy stories and laughs.  One day Sarah shared a “hot mess” picture of her dropping her son off at preschool. She obviously looked stellar, but it sparked a conversation about what is acceptable to wear to your child’s school. Being the teacher of the group I chimed in with real life cases of what NOT TO WEAR.  I asked if I could write a guest blog for Sarah, and she told me to go for it. So here it is 5 things not to wear to your child’s school. All of which I have seen.

  1. Pajamas with cartoon characters that no longer have working elastic.  

I am not one to criticize wearing pajamas out in public.  School spirit pajama day is one of the highlights of the year for me.  Also, every year on pajama day, I somehow always end up running an errand after school in my pajamas.  I have been known to forget pajama day, schedule a parent teacher conference for that day, and ended up sitting across from a parent discussing important matters in my pink polka dotted pajamas.  I get sometimes you are running late to school and you fully intend to shower after dropping the kids off. Come in your pajamas. If your pajamas are plaid flannel, or solid sweatpants, teachers probably won’t even notice.  However, if you are wearing obnoxious character pajamas to a scheduled meeting we will take notice, but probably only roll our eyes. If you have to hold your Tazmanian Devil pajama pants up the entire time we are talking and they end up falling down when you have to sign your name because the elastic is completely shot, you should rethink your wardrobe decisions and use those pants as a rag.  If these are the only pants you own, I don’t believe you.

2. Black leather catsuit.

I love school dress up days and if you are helping at the classroom Halloween party by all means dress up.  However, if you are also planning to wear that costume to the strip club later that evening, just come in blue jeans and a t-shirt.  Teachers do not want to explain to young students about camel toe. And if that costume contains a whip, just leave it in the car.

3. A low cut tank top with no bra

If you are comfortable without a bra, more power to you!  However, please be sure when you lean over and then stand up your nips are still covered.  Teachers will judge you if your tank top all of a sudden is acting a push up bra. I for one cannot concentrate of what you are saying, and I will not remember to print out and send home another copy of the permission slip because I won’t remember you asking for it.  On second thought, I hate to go against a feminist movement. If you are a spokesperson for “Free the Nipple” wear what you want, but don’t hold me responsible for remembering what you said. (I am 99% sure the mother in my situation was not trying to make any political point, she just somehow had no idea the top of her tank top was literally under her boobs.)

4. Shirts with swear words on them

When the F word is written on your shirt it is really just as offensive as you saying it to me.  It doesn’t matter how nice you are, the school will think you are an asshole if you come in wearing profanity on your shirt.  If you find yourself in this situation a quick parking lot fix is just turn the shirt inside out. Then we will just think you are scattered brained and not a jerk.

5.  Uncomfortable dentures

I have never worn dentures, so I cannot speak to the merit of denture comfort.  Perhaps all dentures are widely uncomfortable. If you find you cannot go 30 minutes without taking you dentures out and sitting them on the teacher’s desk, just come to our scheduled meeting without teeth.  This is especially true if you credit your lack of teeth due to old age and you are 33. Not only have you caused me to feel the need to sanitize everything on my desk, but now I am wondering if at any given minute my teeth are going to fall out.  After all, I am a year older than you, my teeth are apparently living on borrowed time.

As long as you follow these simple guidelines, you will always be dressed to impressed or at least dressed as to not leave a lasting impression.  

Diana Winchester

I hope you all enjoyed that as much as I did. Thank you Diana! I will always be looking forward to more guest contributor posts from you. ?I know she wanted to make us all feel confident about ourselves and I know I have never thought about wearing a black leather cat suit to my kid’s school so I must be doing something right.

Until next week, XOXO


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