Summer-to-Fall Transition Outfit Ideas for Teachers (That You Won't Burn Up In) - Mommy The Journalist

Saturday, September 19, 2026

Summer-to-Fall Transition Outfit Ideas for Teachers (That You Won't Burn Up In)

I really can't believe that two weeks have already passed since our last real outfit roundup, but here we are. At least we're back on schedule with these, right? If you're new around here, every two weeks I share a roundup of the outfits I wore in real life with links to shop the same or similar outfits.

As a reminder, if you want to keep up with what I'm wearing more frequently, keep an eye on my Instagram, Facebook, and LTK shop. I post my looks more frequently there, although I will admit that internet issues have taken a toll on the frequency of those posts lately.

We are now about a month-and-a-half into the school year, and while it has been a good year so far (especially compared to last year), it hasn't been without its frustrations. These first six weeks have been an exercise in planning and replanning and completely starting over. Honestly, these first writing and grammar units that we're getting close to finishing look nothing like what I had planned them to be. And that's okay. It's just a lot.

In other news, we now have two show pigs -- Donald and Daisy. They're still babies for all practical purposes, so our work with them is mostly getting them used to Alexis and each other since they came from different places. Alexis just did her first ever real project; she researched and designed a solar system model, which turned out really cool.

It is still super hot here. The mornings and nighttime temps are a smidge cooler, but you can't let that fool you into dressing for fall for real. But I am so ready y'all. I've been making small changes in my outfits that whisper fall. I've got nine outfits for you this go 'round. The first week was Labor Day week, so we only had four school days, and I haven't been taking pictures of my weekend outfits since we've been so busy.

Sizing info: I'm 5'2" and weigh about 140 lbs. I wear size 6 or s/m in clothes and size 7 in shoes.
Blouse | Skirt | Belt | Shoes (similar)

When I put this outfit on, I was imagining a tropical island, but my students all thought I was dressing for fall. Maybe it's the shoes? Sometimes a small change like that makes the difference, and these woven mary janes are a nice transition from sandals. They're still open enough that my feet aren't getting hot, and they feel more fall appropriate.

Anyway, I really do like pairing this skirt with bright red, and this blouse is a really good one. I also have it in navy blue, which I wear quite a bit more. It's got such nice details including the ruffle sleeves and a bit of crochet work, and I like that the buttons make it feel a bit more elevated.

This skirt really is so nice, too. It's not lined, but I don't think it needs it. It's tiered and has an elastic waist. I cut the drawstring ties off since they weren't actually doing anything to tighten the waist. The only thing I wish the skirt has that it doesn't is pockets.

I've worn this outfit before with different shoes. I love the print mixing with this one. It feels so whimsical and like it's the perfect amount without being too busy or distracting.

Thankfully, all the pieces of this outfit are still available. The blouse is a bit thin, so you might want a camisole under it. The skirt is nice and lightweight, so it's not hot.

I absolutely love these mary janes. The buckle design is so unique and convenient. Also, they're really comfortable. I also have them in the green color.

How perfect is this dress for fall? I love that brown is trendy right now, so I can stock up on all the things. While I think black certainly has its place in any closet, brown has always been my go to. Anyway, I don't really have a lot of notes on this dress. It's got a cute ruffled collar with a tie detail, the sleeves are puffed with an elastic band, and the waist is stretchy. It's fully lined, but it doesn't have pockets. I got it in the medium; the small was just a smidge tighter than I like.

My mary janes are a mauve velvet. Y'all, I stalked these suckers until they became available in my size, and I do not regret it one bit. They are comfortable and unique. I love them.
Top | Skirt | Belt | Shoes (similar)

This is another repeat outfit, although I think I might have worn different shoes last time I shared it. I can't remember. I need to find some more ways to wear this fun skirt other than this bright pink, eyelet top. I mean, it's perfect, don't get me wrong, but I'd like to wear the skirt more. I'm just having a hard time seeing it in my mind any other way.

This top, by the way, is a great elevated basic. It feels like you're wearing a t-shirt, but it's so much more interesting. It comes in a ton of colors and is a great price. I also have it in white.
Dress (similar) | Sweater (similar, similar) | Shoes

This dress is one of the most versatile things I own. I wear it all the time, both on its own and styled with other pieces. It's so easy to layer. This go 'round I topped it with this open-stitch, dusty blue, short-sleeve sweater that I cannot remember where I bought it from to save my life. Then I bookended it with my blue mary janes.

Honestly, I feel like this is a look that's been on the blog before, just maybe with different shoes since these ones are a relatively new addition to my closet.

I love this look so much. I think it's my favorite of the entire post. And lucky for you, everything is still available!

This short-sleeve sweater is so dang comfortable. It makes me think of something a grandma would wear, but I still love it and wear it as much as I can. You can't see it since I tucked it in, but it's got a pink band around the bottom as well to match the cuffs on the sleeves and the neck. The diamond pattern is a nice, dark purple color, which is how I tied it in with the skirt.

Y'all already know I love these whimsical moth-and-flower-print skirts. This one is a slimmer fit than the blue one I shared earlier and has a mesh overlay. I'm actively looking for more skirts in this style to add to my closet. That's how much I enjoy wearing this one.

I love this style of dress, and I sincerely hope that Old Navy keeps making them, so I can keep buying them in all the colors and patterns. They're so perfectly comfortable. I love that this loose fit -- it's so flattering!

Also, it was really still too warm for boots, but I wore them anyway. Since I was inside for 99 percent of the day, I was alright. I need to get this exact pair in black.

I've worn a version of this outfit before, just without the vest and with different shoes. Technically, this skirt does not have this bright green in it, but somehow it just works. I added the vest to make it a bit more school approved, although I've worn these tanks on their own before (the straps are pretty wide).

Speaking of...this is a really good tank top. I own it in, I think, eight different colors. I wear them all the time -- on their own or under something else. They're soft and stretchy, and it comes in a ton of colors. I also have this exact skirt in multiple prints.

I felt like I was channeling a 90s-era sitcom mom, so I decided to finish the look out with my white canvas sneakers. They're by Rocketdog and so so comfortable. They've got so much padding and memory foam insoles. My goodness, these things are like wearing clouds on your feet. Perfect for teaching.
Sweater (similar) | Necklace | Skirt | Shoes

I love the idea of this outfit. All the colors work so nicely together, but something about the finished product just doesn't click for me...and I can't figure out why. Honestly, it may be that I'm not used to my haircut. It's been awhile since I went this short, so I definitely haven't figured out a styling routine, plus I'm not used to seeing the bangs again.

Anyway, I absolutely adore this short-sleeved sweater. I have it in three colors. Unfortunately, it's no longer available in any colors, which is a shame because it's perfect. My skirt is the sage green floral print version of the viral NASHALYLY chiffon skirts. It is still available, along with at least a dozen other patterns and colors.

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