8 Early Fall Outfits for Teachers - Mommy The Journalist

Sunday, October 25, 2026

8 Early Fall Outfits for Teachers

Welcome in to a new edition of Real Outfit Roundup. I typically update these every two weeks, but Fall Break through off my normal rotation. I promise I did get dressed over that week, but I only have photographic evidence of one outfit.

What I do have for you are eight classroom-approved looks that work nicely for fall, especially if you're having an unusually warm start to the season like we are. We did have a couple of days drop down into cool territory, so you'll see some light layers in today's post but still no full-out sweaters.

Sizing info: I'm 5'2" and weigh about 140 lbs. I typically wear size 6 or s/m in clothes and size 7 in shoes.
T-shirt | Skirt | Belt | Boots (similar)

I've been feeling nostalgic for 90s style lately, and these slip skirts are the perfect solution. I did size up to a large so that they would be a bit looser on my hips. I got it in three colors, and it comes in a bunch more. I decided to pair this one with this record graphic tee that's still fully in stock at Old Navy, surprisingly.

This was the last day for these heeled combat boots that have been in my closet for several years. I'd forgotten that they had started to creak. It also was pouring rain this particular morning, and our current parking lot at work turns into a lake, so I had to walk through ankle deep water to get in the building, which only made the squeaking and creaking worse. RIP boots. I linked to the pair I bought to replace them.
T-shirt (similar) | Skirt | Shoes (similar)

Leopard print isn't exactly groundbreaking for fall, but this skirt is certainly one to get excited about. I needed to replace my leopard skirt this year. The one I'd been wearing got a really big, unrepairable tear in it. This one is really nice, and I think it's going to hold up nicely. It comes in a few color options. I'm wearing the medium.

My coffee club shirt finally sold out. I've seen a few on Depop if you're interested, but the sizes are very limited. Lucky for you, there are a ton of coffee themed shirts out there.
Necklace | Bracelet | Dress | Shoes (similar)

Sadly, this pretty dusky blue dress is no longer available, but Old Navy does still have it in two other fall-ready colors. I really like the way this dress fits, and I always get compliments when I wear it. It's really easy to just throw on and go. I really only ever switch up my shoes and jewelry. 
T-shirt (similar) | Skirt | Shoes

Y'all, I am sad to report that this favorite floral skirt that has been with me longer than almost anything else in my closet has finally bit the dust. I have fixed it so many times, always in the same spot, and now the material is just too thin to repair. I'm so sad. This has been a good skirt to have in my closet. It is still available, though, so I might just replace it.

It was actually cool this day! I was so glad to finally get to wear this yellowy-green cardigan from Old Navy. It is so soft! I really like how nicely it paired with this blue plaid skirt that I picked up from Target recently. It's got some yellow/gold threaded through the pattern and the cutest fringe hem. It's pretty much sold out online, but you can try your luck at your local store.

My shoes were a spontaneous Old Navy purchase. Seriously, y'all, stop sleeping on their shoes. Every pair I've bought has been well-made and comfortable. I really like the criss-cross straps on these mary janes. They're a dark chocolate brown, which will be a nice addition to my fall and winter shoes.

I am officially in love with this sweater dress. It's incredibly soft and lightweight, which is a must for me when choosing a sweater dress. I ordered it in a medium instead of a large, so I'm hoping it won't shrink any. I am wearing slip shorts underneath because it kept wanting to hike up in the back a bit. Nothing too scandalous, but I wanted to be covered just in case.

My boots are from last year but still available. They are not as loose in the shaft on me as pictured on the model, so keep that in mind.
Necklace | Dress | Vest (similar) | Socks | Boots

This is my favorite outfit of the month so far. I love everything about it. And one of my students told me that my style is "just so cool." So there's that.

This is one of those baby doll dresses that I love so much from Old Navy. I've actually lost track of how many I own at this point. I just keep buying them in all the new patterns. Sadly, this one is only available in limited sizes now. I adore the little tiny dots that are all over it.

These are the new black boots I got to replace the pair that died. Would you believe they're from Walmart? These run a half size small in my opinion, but they are so comfortable and exactly what I was looking for in a combat boot.
T-shirt | Skirt (similar) | Belt | Socks | Boots

This is one of my favorite Halloween themed looks to recreate. I love how bright and fun it is. Sadly, the only things that are still available in this outfit are my belt, socks, and boots. You can find my exact t-shirt on second-hand sites like Poshmark; just search for "team spirit skeletons graphic tee."

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