Winter Outfit Ideas for Teachers

by - January 09, 2024

It's been awhile since I did an outfit roundup post, but to be fair, I have been off for almost three weeks. These outfits are all from before or during Christmas break, so not all of them are outfits I wore to school, but they are all outfits I would wear to teach in. Anyway, I thought this would be a good time to share some teacher-appropriate winter outfits now that we're entering the coldest time of the year for my neck of the woods.

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

Sweater (similar) / Skirt / Boots (similar)

This outfit might look familiar, especially if you follow me on Instagram. I also shared it in a post about dressing cold when it's not really cold. Still, this is such a fun winter outfit and I think a fresh take on leopard print since it's not the typical color scheme.

The skirt is the only new piece in this outfit. It's a couple of months old but still available in most sizes online. This is a straighter style than I typically go for. The waist is elastic but I don't find it to be all that stretchy because the skirt itself doesn't have any stretch, so if you've got wider hips you may want to consider sizing up. I'm wearing size small.

I decided to keep the rest of the outfit simple with a fitted crew-neck black sweater that I half-tucked and bit of 90's-style grunge with my favorite combat boots. The only thing I think I would do differently for colder days is add tights.

Dress (similar) / Sweater (similar) / Shoes (similar)

This is one of my favorite dresses. I think it has a very fall feel to it, but I don't really love all the dark colors of winter, so this feels nice and brightly appropriate. The only thing in my outfit that's new is the belt and it came with a skirt so I can't link to it by itself. My dress is sleeveless and has a very small mock neck. It came with a tie sash, but I still can't tie one of those and it look nice, so I either ditch them entirely or opt for a belt instead.

I waffled back and forth between this yellow cardigan and a burgundy one, which would have matched my shoes, but in the end I wanted the overall outfit to feel very bright, so I went with the yellow. For colder months than this, I would probably go with the darker color.

T-shirt / Shirt (similar) / Jeans / Shoes (similar)

This is my go-to comfy-casual teacher uniform. What's great about these jeans is that they don't really look like jeans. They're also incredibly soft and stretchy. They're pricey, but I think they've been worth it for how much I wear them.

Do people still layer graphic tees under button-ups? This is one of my favorite tees, but right now it's not available in white. I linked to it anyway so you can see the other color options, and who knows? They might bring the white back.

How many leopard print skirts are too many leopard print skirts? Asking for...well, me. As you can see, this skirt is a completely different style from the previous one. It's a more traditional color combination, for one, but it's more flowy and made of a more delicate material. It feels fancier than my other skirts, and I always try to dress it down for school.

Sweater (similar) / Skirt / Boots (similar)

This is the last leopard-print outfit for this post, I promise! This skirt has a lighter background, which I love, and the pattern feels more elevated to me because the spots are more defined. It is clingier so I decided to pair it with a more oversized sweater. I won't lie, I mostly left it untucked at school because it was just comfortable and I was moving around a lot, but half tucking it is the more styled version. I saw a video this morning of a fake-tuck that I think would work amazingly with this, so I'll try it next time.

Shirt (similar, similar, similar) / Pants (similar) / Boots

This is a really simple outfit that I've worn several times, but looking at this outfit now, I'm not loving the proportions. I think my shirt is too oversized for the flared bottoms of the pants. I haven't really played around with styling these pants, which I'm not realizing I need to do. *heads to Pinterest*

Shirt (similar) / Skirt / Shoes (similar)

I might have a future as a safari director. I had to have khaki bottoms for a function, and since I refuse to wear khaki pants it had to be a skirt. I don't hate this skirt, though. I love the tortoiseshell buttons, the high waist, and even the included belt. I struggle with styling khaki, though. How do you do this without creating an outfit that just feels brown?

Dress / Boots (similar)

I think I wore this on Thanksgiving, actually. The dress is pretty thin, to be honest, but it could easily be layered. My boots are several years old, but ShoeDazzle has a pair that's almost exactly the same.

Sweater (similar) / Skirt / Boots (similar)

This is pretty much the same outfit as the green leopard-print skirt but with a dusky blue floral skirt instead.

Dress (similar) / Tights / Boots (similar)

Dresses really are my go-to outfit of choice. The only decision I have to make is what shoes to wear. Sometimes I add another layer or accessories, but this dress really doesn't' need anything extra. I linked to the exact dress, but this specific color isn't available anymore, so I linked to a similar dress that is closer in color.

Sweater / Skirt (similar) / Boots (similar)

I love this skirt. It's definitely got spring vibes, but when have I ever let that stop me? Especially when I found this fuzzy hot pink sweater that Cher from Clueless would absolutely die for. This is still available and in other colors, too. It's such a comfortable sweater, y'all. It's the eyelash style on the outside, but it's not itchy or anything on the inside. It's nice and smooth. If you don't see your size online, check your local store. Mine still had a bunch of these in stock.

Sweater / Pants (similar) / Boots (similar)

There's just something about an all-neutral outfit that does it for me. This style of boot is certainly not trendy these days but they're classic and never really out of style. I like how they provide an anchor for this outfit without being overly bulky. It feels like a nice balance for the tunic sweater.

Sweater (similar) / Jeans / Boots

I don't remember when I wore this other than it was during the break. I do remember taking specific steps to style it like cuffing my jeans, half tucking the sweater, and adding a belt. My sweater is several years old and no longer available, but I found a really close match.

My boots are new. They were a Christmas gift, but I linked to the exact ones. I love these boots. Unfortunately, I kicked something and have a really deep gouge right on the top of the left one now that I'm trying to figure out how to fix.

Sweater (similar, similar) / JeansBoots

Another outfit with my new boots! This sweater is no longer available, but I found two similar options that I might actually like better than this one. I wanted to wear it over leggings, but it wasn't quite long enough for me to be comfortable wearing it out in public, so I swapped to skinny black jeans. The brown combat boots help pull out the earth tones of the sweater and balance them with the darkness of the jeans.

And here's a closer look at the boots.

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