Real Outfit Roundup: 9 Winter-Approved Teacher Outfits

by - January 26, 2025


I can't believe two weeks has already passed since my first outfit roundup of 2025! As promised, I'm here to share the looks I wore in real life with you along with brief explanations behind the outfits and links to shop the same or similar products.

I must point out, however, that there are definitely not enough outfits in this post for two weeks, but I have a valid reason! We've been snowed in -- in south Alabama, no less -- so there have been a few days in a row in which I didn't actually get dressed other than in undistinguishable layers to traipse in and out half a dozen times to make the most of the snow days we may not see again for another thirty or so years.

Sizing info: I'm 5'2" and weigh around 140 lbs. I typically wear size 6 or S/M in clothes and 7 in shoes.

Blouse / Skirt / Belt / Boots (similar)

This was our first Monday back at school after Christmas break. We were doing a school-wide writing benchmark test this day so I didn't have any active teaching beyond going over that week's vocabulary words and reading the instructions for the test.

This is my favorite outfit with this skirt so far. I got it way back at the start of the school year. It reminded me of a skirt I used to have in the mid-aughts that I had to donate because of post-partum body changes. I've not been able to find a suitable replacement until this skirt, which feels like an updated version that is a nice fit for my current age. The buttons are functional and it has both front and back pockets. It's high-waisted, which I really like for my shorter stature. Because of the functional buttons, I sized up to an 8 to prevent unsightly gapping, but if that's not an issue for you, I'd say go with your true size. This is non-stretchy denim, though, so keep that in mind. It's surprisingly still available in almost every size.

This blouse has quickly become a staple in my closet, filling gaps I didn't even know existed. I sized up to a medium, and I'm glad I did because it shrank a bit in the wash. It's really only noticeable in the sleeve length, though.

Blouse (similar) / Vest / Pants (similar, similar) / Boots

This was such a fun outfit! Even my students loved it. I've gotten really into sweater vests this year, especially ones that have personality, and this one certainly has that in spades. I've been mostly avoiding the current bow and tie-top trend. I don't foresee it lasting all that long, but I couldn't pass up this bow-tie sweater vest. Well, that's not true, I almost did pass it up because it had so few reviews, but I'm glad I took the chance. It's really well-made, and I love that you can wear it with the bows in the front or the back.


This first go round, I layered it over an old Liz Claiborne polka-dot button up that I've had for years. Because I felt like the buttons would look odd with the bows, I wore it with the bows in the back. I didn't have anyone to take my picture from behind, so this is the best view I could get for y'all.

Anyway, I went with my gray Liverpool skinny jeans that I've had for awhile, and my black heeled Chelsea boots finished the look.


I love this skirt so much, but I have had a tough time styling it. It's a color and texture issue that I just have not been able to work out. I ordered this blouse specifically with this skirt in mind, and it's so perfect with it. So I've definitely got the texture figured out; now I want to figure out how to wear more than just this neutral beige, but the colors so far have been impossible for me to match. I will figure it out though!

We were done with testing by Wednesday, so I had a full day of actual teaching. We started our new writing unit, which meant I was on my feet and moving around all day long, so it was a good opportunity to give these loafers I got for Christmas a test run. It was really cold this day, so I did wear some flesh-colored tights underneath the skirt for an extra layer. I wasn't really thrilled with how the tights looked with the shoes (they're actually too light for my skin tone, believe it or not, but it was what I had on hand), but I do love the shoes with the rest of the outfit.


I told y'all I was going to order my favorite overalls in green! And as predicted, I love them a whole lot. I did have to let the straps out almost all the way to get them to sit where I like them. Otherwise, they were way too snug in the crotch area, if you know what I mean, and they looked goofy with my boots.

It had warmed up a bit this day, so I was comfortable in a short-sleeve blouse, especially since the heater in my classroom kicked into sauna mode. I definitely ordered this one with the intention of wearing it with these overalls, but it will blend in nicely with the rest of my closet, as well. It's got a cottage core vibe that I really love.

Sweatshirt / Jeans (similar) / Shoes

Casual Friday, anyone? I was going for casual preppy here, but I didn't love this outfit. It was definitely the socks-and-shoes combo. The bright white of the socks just slapped me in the face every time I looked down. But one of my students told me that my 'fit was fire' so I guess there's that.

I love a graphic sweatshirt. It's actually pretty much the only way you'll get me to wear one. I don't find them to be particularly flattering on my body type; they're just so bulky, ya know? I do like this one, however. It's very soft and warm, so I was comfortable in it all day long.


Have you gotten one of these sweatshirt dresses yet? If you haven't, you're surely missing out! They're so great.

I wore this the Saturday before the big snow storm. The cold front was starting to move in, and it was so windy! For that reason, I layered my one and only pair of leggings underneath the dress. I wanted flat shoes, so I went with my old favorite buckle boots that my mom still hates. Alexis had Odyssey practice, so we dropped her off there, then dropped her overnight bag off with my parents. We came back home where I did some homework, then we drove to a nearby town for a date night dinner at our favorite Cajun restaurant.

SweaterPants (similarsimilar) / Belt / Boots (similarsimilar)

I am trying to rack my brain for what we did on Sunday, but I cannot for the life of me remember. I think we might have gone to the grocery store. I do remember that the temperatures dropped drastically throughout the day, hence two different outfit pictures for this particular day. I started out with just gray jeans and a cream-colored sweater with boots.

This sweater is going to be a favorite, I can tell. I've already worn it several times since it came in just after the new year. I really love Old Navy's SoSoft line. They're amazingly cozy. The only complaint I have about the sweater is that the neck is a bit too high for my neck.

Sweater / VestPants (similarsimilar) / Belt / Boots (similarsimilar)

Then, when the temps dropped significantly, I layered this faux leather vest over the sweater. I ordered this vest with very low expectations. It's a lot puffier than I usually like, but I got it for under $15 so I figured what the heck. No one is more surprised than me by how much I love it. I didn't feel like the Michelin man while wearing it, and I was pleasantly surprised by how warm it is. Now, I will say that when I first opened the packaging, it smelled horribly, but it faded after a couple days of airing out.


We're skipping pretty much an entire week. I remember what I wore on Monday and Tuesday, but for whatever reason I didn't take any photographic evidence. Then Wednesday and Thursday, I was so bundled up you couldn't tell what I was wearing. Plus, every time we came inside from the snow, I changed back into pajamas.

This was Friday. We woke up to snow still on the ground but not nearly as much as the day before, and it was melting quickly. For the first time since coming home from school on Tuesday, we got out of the house. We went to lunch and then walked through Target and the book store. It was still cold, but nowhere near what the previous three days had been, so a sweater was still appropriate...and yes, this is the same sweater as the previous outfit. I told y'all I've been wearing it a lot!

I layered the sweater underneath these patchwork overalls that are so cute in person. In hindsight, I think the sweater was a little too bulky for the overalls -- they look a little lumpy in this picture -- but I did really like this outfit.

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