Back-to-School Outfits for Teachers

by - August 13, 2023


The first two weeks of school are officially under my belt. It's been a good two weeks other than the issue with the air conditioning on my hall not working properly. We've been under heat advisories pretty much every day, and my hall, which is essentially the main corridor of the entire building, has been sitting at a cool near-80 degrees for the past two weeks. Technically the a/c in my room is working, but technically isn't really cutting it. I feel like I've been stuck in a never-ending hot flash, y'all. Meanwhile, my kids, who aren't in a constant state of movement once they get in my classroom, are complaining about being able to feel the barely-there cold air coming out of my wall unit.

Anyway, all that to say that my outfit choices for the first two weeks are absolutely a reflection of the whole a/c situation. There are only eight days shown here because I missed a day to take my content certification test, and I just forgot to take a picture one day for whatever reason.

Sizing info: I'm 5'2" and weigh about 135 lbs. I typically wear size 6 or s/m in most clothes and size 7 in shoes.

Cami / Vest (similar) / Skirt / Sandals

Is this a repeat outfit from last month? Yes, yes it is! I wore this exact outfit to one of my summer classes and then again for the first day of school.

Dress (Wantable) / Shirt (similar) / Shoes

This is one of my most repeated outfits. I really do just love it that much. The dress is one of my favorites by itself, but the top is not school appropriate (spaghetti straps and a tad too low), so I always wear something over it for school. I almost always wear my Adidas sneakers with it when I teach. I can't explain why I like the combo so much, but I do.

T-shirt / Jeans / Shoes (similar)

I feel like I've shared this outfit before, too. I know, for sure, that I've worn it to school before. None of my students got the band reference, though, sadly.

Sweater / Skirt / Shoes (similar)

Does that say sweater? Yes. And, yes, I regretted wearing it by the time I got to second period. It's cute, though, and usually a good choice for warm days. I don't recommend it for triple-digit feels-like temperatures, especially if your a/c is struggling.

That said, this might be my favorite outfit from this roundup. I love this skirt. It's tiered, which is difficult to tell in this picture. The length is my favorite for me. It's not lined and it doesn't have pockets, but it's not see-through and the waist is elastic.

T-shirt (similar) / Shirt (similar) / Pants (similar) / Sandals

This was my attempt to recreate an outfit from a few years ago. It's essentially the same but I swapped out a denim jacket for a short-sleeved chambray button-up. My sandals are also different, but the pair I wore then wore out and had to be replaced.

I won't lie. I like this outfit in the picture, but in real life I felt almost sloppy wearing it. I think because everything was so loose and that's just not my usual style. I was comfortable, though.

Shirt / Jeans (similar) / Shoes (similar)

Another outfit repeat from my summer class? Yep! This was probably the hottest day of the last two weeks for me...and I was working through a migraine. It was not a pleasant day, but I survived.


I'm pretty sure I wore this at the end of last school year when we were doing Maui and Moana. The only difference this time would be my shoes, which you can't really see because the skirt is so long. They're these really cute straw wedges. Unfortunately, they might not work for teaching. About halfway through the day, my feet were dying, and I had a huge blister on the bottom of one of my big toes.  They weren't uncomfortable, per se. I just did a lot of moving around the classroom this day for whatever reason, and these were not the shoes for that. Consider yourself warned.


This was my first official Friday, since I missed the first one to take a test. We get to wear jeans on Fridays so I used the opportunity to break out my new denim skirt. It's just above knee-length and has functioning buttons all the way down. The pockets on the front are decent sized. There are no back pockets, which I didn't realize until I got it. It's not stiff denim but it's also not as stretchy as I hoped it would be. I'm wearing an 8 but probably would have been comfortable going up to a 10 for a bit more room.

My blouse is old but still available. It comes in a bunch more colors/patterns. It's a classic shape. I will say that the sleeves/shoulders may be tighter than you want. I'm wearing a medium and they're on the small side.

These slip-on sneakers might be my best purchase this summer. I have been wearing them all the time with all kinds of outfits. This exact pair is starting to sell out so if you like them, better hurry.

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