Real Outfit Roundup: 10 Fall Outfits for Teachers

by - November 16, 2024


I did not intend for another week and a half to pass before I had a post ready for you, but that's life. Anyway, I've got eleven outfits from the past month to share with you. These include a couple of homecoming week outfits, one of which definitely doesn't really fit the fall vibe, but 

I've been trying to do better at keeping my Shop My Instagram page updated since I've not been so great at regular posting, so most of these have already been posted there. You can keep up with that by clicking the "Shop My Instagram" link at the top of this page or by following my Like to Know It Shop directly. I've also got a widget in my sidebar that shows the six most recent outfits I've shared.

Anyway, on to the fashion. For size reference, I'm 5'2" and weigh about 140 lbs. I usually wear size 6 or s/m in clothing and size 7 in shoes.


This was the first day of Homecoming week, and teachers were strongly encouraged to participate in the dress-up days. Day one was hat day, which obviously I'm not wearing in this picture. I don't wear hats unless I'm at the beach or on a boat, but I do have one of those newsboy-style hats from way back when they were trendy, so I decided to style an outfit that wouldn't feel out of place while wearing it...although I did not wear the hat all day long.

I love this skirt. It's a layered mesh slip skirt, so very late 90s-early 2000s vibes. It's super stretchy so very comfy. I don't remember how I landed on my spooky book shirt, but this is a fun, seasonally-appropriate graphic tee. It's really soft and not super fitted. Because everything about the outfit felt casual, I went with my favorite Adidas sneakers.

Shirt / Skirt (similar) / Shoes

The theme for this day was color wars. Teachers were supposed to wear a blue shirt, so I styled my outfit around this bright blue blouse. My skirt is several years old, but my blouse is still available. It comes in lots of colors.

Shirt / Joggers / Boots (similar)

Yep, you guessed it. Another dress-up day. The theme was camouflage. My shirt is just a basic, long-sleeve t-shirt that I picked up at Walmart for $5. My pants are still available and under $20. My boots are old, but I linked to a really similar pair by the same brand.

Dress / Boots (similar)

I love this dress so much. The color is "coral" but in person it's like a coffee brown, but it's so pretty. This color, unfortunately, is almost sold out, but it also comes in green and burgundy. It's not lined, which makes it perfect for our never-feels-like-fall fall.

My boots are from 2022 so no longer available, but they are my favorite tall black boots. They're faux suede and the perfect height. Despite having a heel, they're comfortable for all day wear, even as a teacher. I linked to a similar pair by the same brand.


I really enjoyed this outfit, even though I was definitely overdressed for the weather. Yay for air conditioning.

This sweater is such a classic, from the houndstooth print to the pearl buttons. It can definitely be worn on its own, fully buttoned up, but because it was warm this day, I wanted to be able to lose it if I got too hot, so I added a pop of red underneath with a basic camisole.

My skirt is a few years old but still available. It's got undershorts built in, which helps keep it school appropriate.

I showed these Mary Janes in my last post with the note that I didn't know if I'd be able to keep wearing them. Well, I'm happy to report that I was able to stretch them out by wearing them around the house with socks. Now they aren't too tight and no longer rub blisters on my heels.

Shirt (similar) / Overalls / Boots (similar)

I was feeling inspired by the Addams family for this outfit, but I absolutely love the way it turned out. These overalls have been such a great addition to my teacher wardrobe. They're a nice sturdy material, which was a nice surprise from the flimsy linen I was expecting.

My blouse is really old. I think it came in a StitchFix box, but there is a really cute, similar blouse I've been eyeing on Amazon with a more modern statement sleeve that I linked to. I do love a statement sleeve, and these trumpet/bell sleeves are always a winner in my book.

I finished the look with a pair of combat boots.

Shirt / Pants (similar) / Belt / Shoes (similar)

I really enjoyed this outfit at the time that I wore it. The neutral colors with pops of red felt very seasonally-appropriate without smothering me with too-thick fabrics. Unfortunately, the only part of this outfit that is still available with no restrictions is the belt.

My blouse is only available in limited sizes, but it does come in two other options and if you browse the website, there are some similar style shirts in different patterns. My pants aren't even available to link to, which is really sad because they are a great pair of pants.

My flats are several years old but surprisingly still on trend because they're true ballet flats, little bow on the toe and all. They're no longer available, but I linked to an even more on-trend style in the same color.

Sweater (similar) / Pants / Shoes

I like the idea of this outfit, but in person, the proportions didn't really work. I'm wondering if it's because my shoes were flat. Certainly, adding a bit of height to the bottom would have helped, but I think the sweater was too boxy for the cropped, wide-leg style of the pants.

Anyway, my sweater is sadly no longer available, but I linked to something that's kind of similar. My pants are still available in most sizes, as are my Mary Janes.


My mom inspired me to put this outfit together. You've seen all these pieces before, just not together. Everything is still available. I do recommend sizing up in the skirt as it has very little give in the denim. I sized up to an 8 to keep the buttons from pulling and gaping, which is really unattractive.

Sweater / Skirt / Boots (similar)

Hello, academia. This outfit made me feel like a teacher.

This skirt, while not labeled bodycon, might as well be. I sized up to a medium but probably could have gone with the large and had no issues. I did find it odd that the zipper closure was on the right side instead of the left, which makes it awkward to maneuver closed. It's doable, just not convenient. The skirt is lined, and the liner is attached in a way that you don't have to worry about it riding up and causing lumps or peeking out the bottom.

My polo sweater is from last year, but it's still available...I think. At the very least, the one I linked to is by the same brand and looks remarkably similar.

Shirt / Pants (similar) / Boots

My students are always so funny when I wear things they consider "theirs." Let me share with you a conversation from the day I wore this.

Student: (incredulous) You're wearing cargo pants?!
Me: (looking at my neighbor teacher who's my age; she smirks) Y'all didn't invent these.
Other Teacher: Nope. We did.

Anyway, I picked up these cargo parachute pants from Walmart. They're no longer available on the website, but I'm pretty sure I saw them still in my local store. At any rate, I linked to a pair that looks pretty similar.

My t-shirt is one of my favorite graphic tees, and my boots are my go-to this time of year for practically every outfit.

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