Back-to-School Shopping: Teacher Edition

by - July 21, 2022


The countdown to back-to-school is getting shorter. For me, my school year started this week with orientation. I've got pre-planning next week and then the kids start the week after. So for the past month or so, I've been working on adding teacher-appropriate items to my closet, specifically some easy-to-style pants and longer skirts and dresses. Everything I've bought can be mixed in with my existing wardrobe fairly easily and also works for casual out-of-school dressing, as well.

*This post does not contain the items I received in my first Wantable box that I kept with the intention of wearing them for school. You can check that post out here.

Take a look at the clothing items I bought specifically for school.

Let's start with the items I got from Amazon.

Black Floral & Yellow Floral Tiered Midi Skirt - These skirts are so good, y'all. They are fully lined, which is great, but the material is pretty delicate, so probably not appropriate for working with younger kids. The waistband is elastic, so it's got some give to it. It does not have pockets, which makes me kinda sad. The skirt is tiered, so it has a really pretty flow. They come in several other colors. (See how I styled the yellow skirt in this post.)

Green Floral Maxi Skirt & Blue Plaid/Gingham Maxi Skirt  - These are technically the same skirt, just in very different, seemingly unrelated patterns. What I like about these is how sturdy the material is. It's thick without being bulky and doesn't need a liner underneath. The waistband is elastic so not restrictive. (See how I styled it in this post.)

Colorful Tassel Earrings - Ok, so I didn't buy these specifically for teaching, but they're still a great find and an easy way to add a dash of fun to any outfit.

Blue & Yellow Striped Maxi Dress - I am so happy with this dress. The material is a polyester blend and is a little stretchy, but I don't think it's going to lose it's shape. It does have a side zipper, and the waist is not elastic, so be aware of that when ordering. Also, on me at least, it shows just a hint of cleavage, so I'll most likely add a camisole underneath for modesty when wearing at school. But for all you non-teachers out there, this would be a good casually dressy option for lots of occasions! Oh, and it has pockets!

Black & White Maxi Dress - I don't know what to call the pattern on this dress. Square polka dots maybe? Anyway, I am in love with it. It's very roomy, especially since I ordered up to a medium. I'm not sure I would like the chest area to be any tighter, and it might shrink in the wash. I feel like this one has good movement capabilities.


Let's talk about pants. I, personally, have a really hard time buying pants that aren't jeans. Petite sizes, while being perfect in the leg, are typically too short in the crotch area, but regular sizes almost never fit quite right unless I'm able to find cropped lengths, which fit me like ankle length. That said, I found some really good options at Old Navy that I wanted to share with you.

High-Waisted Chinos - I am not a fan of khaki pants at all, but I really do like these colored chinos. They're like wearing colored denim but in a material and fit that's more work-appropriate. I got these the in Panther (gray) and Dusty Cedar (pink) colors. Going into the fitting room, I was prepared to be disappointed because of the elastic back on the waistband. Obviously, I was not since I walked out of the store with two pair. On me, these are ankle length, and the fit is really good for my body shape. They've got them in several other colors, so if you're looking to add some color to your bottoms, definitely check these out.

High-Waisted Black & White Striped Linen Pants - I had been looking at these online for a really long time but never committed. I have a hard time with linen pants. I always feel like they look kind of sloppy on me, but these made me feel like I was dressed for success while feeling like I was wearing pajamas. I can't wait to style them.

High-Waisted Wide-Leg Linen Pants in Miner's Gold - These fit pretty much the same as the other pair of linen pants, but they're different styles. I really love this color, and it's almost a perfect match to my school colors so that's a win-win!


The Sonoma Goods for Life brand at Kohl's is one of my favorites for comfortable pieces that still look polished and professional. Right now, they have a ton of great work-ready dresses.

Button-Front Midi Shirt Dress - I love a good shirt dress, especially one that buttons all the way up. They just feel effortless. I like the curved hem on this one a lot and that the collar isn't super big. It does have a tie waist, but you can easily remove it and use a regular belt instead. It comes in this blue indigo quit print and a few others. (See how I styled it in this post.)

Ruffle Midi Dress in Multi Floral - If you've been a reader for any amount of time, you're well acquainted with my love of floral print and already know that I couldn't pass by this dress without at least trying it on. This is one of those dresses that's flattering for most body shapes. My mom bought the exact same dress in a different color, and it looks just as nice on her as it does on me.


The Time & Tru brand at Walmart has become one of my go-to's for pretty much everything in the last few years but especially basics, or the building blocks of my closet.

Time & True Tank Dresses - These tank dresses are one of those things that you can build so many different outfits around. That's probably why I own four of this year's versions: shazam blue, beige stripe, soft celadon, orange mango. These are super soft, easy to move in, and have pockets. You can wear them on their own or layer a jacket or shirt over them in cooler weather, and you can wear almost any type of shoe with them. Sizing note: On me, these dresses are past my knee, which is a pretty big difference from these models. 

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