Real Outfit Roundup: 2 Weeks of Winter Teacher Outfits

by - February 08, 2025


Wow, these last two weeks passed in a blur! There's been a lot going on - so much so that it's actually kind of hard to focus on what actually happened, but I'll do my best.

My last outfit roundup came right after our major southern snow event, which is still causing a bit of chaos weeks after the snow is gone and the weather has fast-forwarded a couple of seasons. Seriously, it's been 80 degrees this week, y'all. Anyway, we missed basically a full week of school, had to shift our state-mandated benchmark testing, and are still figuring out how to adjust our lesson plans to ensure we cover all the things we need to before end-of-year testing...and we've still got two week-long breaks in our schedule between now and then!

We're also preparing for the regional and state hog shows, which are now only a week away! That means lots more time spent at the barn. Alexis's Odyssey practices have ramped up, too, with longer weekday practices and more weekend practices. The regional competition is less than a month away now.

So life has been incredibly busy these days. But I have been dedicated to documenting my outfits over the last two weeks, at least on work days, so I've got ten whole outfits to share with you! Let's dive in to what I've been wearing.

Sizing info: I'm 5'2" and weigh about 140 lbs. I usually wear size 6 or s/m in clothes and size 7 in shoes.


This was our first day back after being out a week for snow. It was still pretty cold, and I couldn't wait to wear this graphic sweater vest. It's from Cider, which is a brand I've been wanting to try. Apparently they sell through Amazon as well as their own site. Anyway, this vest is really good quality. I was honestly surprised. It's very soft and nice and warm. I paired it with a mustard-yellow blouse I've had for several years (I think I got it in either a StitchFix or Wantable box) and this pretty neutral plaid skirt.

The skirt is wool. It is fully lined and has a side zipper closure. It has no stretch, so if you're between sizes I would probably go up one. I didn't 100 percent love the shorter lace-up boots with it. I think my knee-high ones would have probably looked better. I feel like there's just too much skin showing.

I've had these sweater socks for several years now, and they are my go-to winter socks. They keep my feet warm without making them sweat. They are cute patterns with fun colors. I highly recommend them.

Blouse / Jumper / Boots (similar)

This corduroy jumper is still in rotation, y'all. Although I do have to admit that I was a bit uncomfortable in it this time around, and I can't really explain why other than to say that it felt so much shorter than the other times I've worn it. But I've compared pictures, and it definitely is not! Maybe it was because this was the first time I didn't have tights/leggings? Anyway...

You've already heard me wax poetically about how great this jumper is, so this go 'round I'm going to wax poetically about this beautiful lace blouse. It's so good, y'all. It has pearl buttons and the cutest ruffle detail on the cuffs. It is sheer, so I wore a basic light pink camisole underneath. I got the medium, and it's a little loose but I feel like it'll shrink some in the wash. It comes in several other colors. I really like the light blue -- it's a perfect match for a favorite skirt of mine!

T-shirt / Skirt / Belt (similar) / Shoes (similar)

I wish I could say that I wore this ballerina bun all day long, but I did not. In fact, I had a really terrible hair day and only pulled this bun together when I got home...and it looked amazing. Now, had I tried to do this for school that day, it would not have worked out at all. But, I digress. You're here for the fashion, not my hair woes.

Anyway, the weather had warmed up by Wednesday, so short sleeves was appropriate...outside, at least. The building had decidedly not warmed up. I grabbed this Dolly Parton tee on sale from Old Navy and just had to pair it with this old favorite pink polka dot skirt. I didn't like the way the waistband looked when I tucked the shirt in, so I added this wide braided belt, which I realize is very much off-center in this picture. Oh well, it was that kind of day.

It's kind of hard to see in the picture, but I finished the look with my gold sparkly ballet flats. I've had these awhile, so they're no longer available, but I found a pair that looks pretty similar and has good reviews.


I am in love with this dress. It is so comfortable. It is a ribbed material but not as thick as a sweater. It's nice and heavy, though, so it's flattering and not overly clingy. And this color! So pretty, and a nice alternative to pink or red for Valentine's Day. It is currently on clearance, but still available in all sizes!

My heels are slingback block pumps that I got on major sale at Old Navy. I've been avoiding this trend because I don't generally love slingbacks. But they seem to be sticking around, so I decided to try a basic pair, and I have to say that I might have been wrong about this trend. I actually love this pair. They are very classic and feel elegant without being over the top. These also have a cushioned footbed, which I appreciate. Unfortunately, they are almost completely sold out, but I did find a couple pairs that are similar for you.

T-shirt (similar) / Jeans / Belt / Boots

I am still in love with these jeans, y'all. This go 'round, I decided to throw in a little more color and skip the monochrome look with this graphic tee featuring a vase of flowers. It's from last year so no longer available, but I found a really cute blue-and-white graphic tee featuring a French breakfast that would create a really similar look for you.


This was a fun outfit for a Monday. I wanted to challenge myself to do two weeks of Valentine's-appropriate outfits that didn't necessarily scream Valentine's Day. Don't get me wrong. I love a good graphic tee, but I don't love having a lot of holiday-themed clothing items that can only be worn once a year, so I tend to focus on color combos instead.

This pink-printed "Let's Go Girls" tee is a perfect example of a Valentine's-esque top that can be worn all throughout the year. I picked this up at Tractor Supply, but there are lots of different versions of it. I linked to the exact and another one that's almost exact. I paired it with this pink-and-blue floral print slip skirt that's several years old. Sadly, this beauty is long gone, and I've been unsuccessful in finding a dupe, but I did link to a nice slip skirt that comes in a bunch of options for you.


This one is a bit of a stretch for Valentine's Day, but the t-shirt has a heart on it so I say it counts! I had a teacher workshop this day and really just wanted to be comfortable.

I don't tend to like khakis, but these are okay. They're at least more comfortable than khakis. These pants have a stretchy waistband like sweatpants. This color is called "wishbone," but they come in six others. I'm intrigued by the "skylark" but have no idea how I would wear them.

Shirt / Skirt / Socks / Shoes (similar)

I had a lot of fun with this outfit...but my students were very much concerned with my choice of footwear. "Why are you wearing bowling shoes?" they asked. Or, "Are you a tap dancer?" Only the other teachers appreciated my Oxfords and overall look. My mom said I needed to be going to a sock hop. Mine are admittedly very old and the exact ones are no longer available, but you can find these everywhere. I linked to a pair with really good reviews and a middle-of-the-road price point.

Anyway, cherry print must be a thing this year because I have been seeing it everywhere. Don't get me wrong - I love it! Brings back so much nostalgia. This one is really cute. It's a ribbed t-shirt material with lettuce hems on the sleeves and waist. Sadly, the buttons are just for decoration. Be aware that it is fitted and fairly short-waisted. It's not advertised as being cropped, but it's very short.

This skirt is one of my favorites. It's actually three layers, which is so interesting. It's very stretchy and transports me right back to the 90s every time I wear it.


As you can see, by Thursday I had completely forgotten my goal of wearing Valentine's appropriate outfits. Oops. But this outfit might be my favorite of the entire batch.

I used to have a dress in this same pattern that I wore until it was basically falling apart. This skirt feels like a more grown-up version of it. It's got such great details. I love the little pom-poms at the hem and the band of lace near the bottom. I found it at Cato at the start of the school year, so you know it's long gone since they don't keep styles around long. I found two skirts that kind of have the same vibe, though.

My shirt is a textured lace. It's technically sheer but not to the point that I felt like I needed to add an underlayer. It's hard to tell in this picture, but it has small bell sleeves. If you've been around the blog awhile, then you'll know I love a good bell sleeve. I did order this in a medium, which I don't regret because the top is so fitted, but it did make the scoop neck really wide, so if you've got narrow shoulders it could be a problem. It is currently on clearance but still available in most sizes and comes in a few other colors, as well.

Dress / Boots (similar)

This brings us to the first Friday in February, and once again I did not dress for Valentine's Day. However, this dress does come in several Valentine's-appropriate options so not a total loss. I've had this particular one for a couple of years now. It's listed as the "green" option, but as you can see, it's not really all that green. I guess you could consider the bottom a really light sea-foam, but classifying this as a "green" feels like a stretch. Anyway, it's a great dress.

My boots are several years old from ShoeDazzle. The exact style is no longer available, but the Hally is really close. I wear a 7 wide calf.

You May Also Like

0 comments