Real Outfit Roundup: Hello Winter - Mommy The Journalist

Sunday, December 14, 2025

Real Outfit Roundup: Hello Winter

Winter has finally arrived in the South! That means this edition of Real Outfit Roundup is filled with cozy layers and warm (but not stifling) sweaters. These are the outfits I wore to work over the last two weeks, minus the first Friday because I legitimately forgot to take a picture before I changed into my pajamas after school.

There are a lot of old favorites in this post, including my favorite boots to wear this time of year, some timeless Fair Isle, and the only pair of leggings I've owned over the last decade or so. I feel like I'm finally finding a rhythm of mixing all my favorite items together to create outfits that aren't necessarily "flattering" (i.e. that make me look a size or two smaller) but that feel timeless and effortlessly me. It probably helps that all the darker hues of the colder seasons are my best, and favorite, colors to wear.

I definitely was experimenting with less structured looks with these outfits, which is very much not the norm for me at all. I love a good belt and defined waist, but sweaters are trickier in that area due to their bulk. As a petite person, I try to avoid adding bulk to my waist because it just weighs me down and makes me seem even shorter. I want to be tall, dammit! Anyway, the less-defined look is taking some getting used to, but it's growing on me...and it sure is comfortable.

On to the outfits! For those of you new to this series, every two weeks I share the outfits that I wore in real life, usually to work as a middle school ELA teacher. I try to give a brief explanation about each look and then share links to shop the exact or similar pieces.

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 Thanksgiving break. That entire week was cold and rainy, so I embraced the rare opportunity to fully immerse myself in winter fashion.

I've had this gorgeous embroidered sweater for a little bit now, just waiting on the weather to cool off enough for me to wear it. Honestly, I was expecting that to be January because this one is very cozy. It's a wool-polyester blend, and it does not let much wind through. It's very thick. I'm happy to note that it's more soft than itchy, so I didn't feel the need to wear anything under it, which is rare for me. Unfortunately, this cream color is no longer available but it does come in five other colors.

I decided to pair it with this favorite brown plaid skirt that I've been wearing over and over again this season. I like that it's not super thick, which means I'll be able to wear it a bunch. I did struggle a bit with how to wear the sweater over this skirt. I didn't love it untucked, but it was too bulky to fully tuck, and I don't have one of those stretchy sweater-tucking belts. I managed to kind of mimic what those belts do, though, by only tucking the waistband of the sweater into the skirt and then carefully adjusting the blousing all the way around.

I finished the look with my favorite lace-up boots that I legitimately wear with everything. They're definitely my favorites.
Sweater | Pants (similar) | Boots

I found this sweater at Walmart and knew that I needed it. I love the blue-and-purple stripes, and it's a really nice quality. This is a sweater that I know I'll be wearing for years to come. Lots of other people feel the same way apparently since it's already basically sold out online.

I decided to pair this with my blue pinstriped Billie pants from Old Navy for a little stripe-on-stripe action. These have completely sold out now and aren't even showing up on the website anymore, which is a shame because they really are that good.

I finished the look with my second most-worn boots, my chunky heeled Chelsea boots that I also own in black. They're good for when I need a bit of extra height, like with a pair of pants that might otherwise be too long.
Sweater | Camisole | Pants (similar) | Boots

How I wish these exact pants were still available to share with y'all. They quickly became one of my favorite pairs to wear in the winter the year that I bought them, but they weren't available for long. They're wool, which means I really can only wear them certain times of year, otherwise I'd probably have a heat stroke. Because my opportunities to wear them are so few, I haven't experimented much beyond pairing them with black. This year, though, I did at least get to wear them with a long-sleeve sweater.

This is another Walmart find that I'll be getting a lot of wear out of...so long as I can stop pulling the stitches. I keep catching this one on everything and having to fix where it snags. Otherwise, this is such a great sweater. I love that it's got the slightly open textured knit. Not only does it give an otherwise basic sweater some visual interest, but it also helps to keep it from being too warm. I did layer it over a black camisole to keep it as modest as possible.

This picture is really not all that flattering, but this was my favorite outfit of the week. I decided to try a less defined look with this sweater-and-skirt combo. It felt so foreign to me to not have that definition at my waist, but this sweater really was too bulky to tuck, and I ultimately just wanted to be comfortable.

This sweater has been really popular -- it's basically sold out! Not to brag, but I bought it before it went viral; it just wasn't get cold enough to wear it yet. It's part of Old Navy's SoSoft line, which lives up to its name. This color is so interesting, too.

I'd been looking at this skirt for awhile online and finally decided to order it. It's not the best quality, but it's also not just total crap. The product page says it's 95% polyester. It's got that slick feeling, which is okay, but not what I was expecting. I love the pattern, though, so I'm going to get as much wear out of it as I can.
Sweater (similar) | Skirt | BeltBoots

Jumping forward to last week, a.k.a. the longest week in December. Man, this week was tough, y'all, especially Monday. Whew. That was one of the worst days I've had at school in awhile. I told a class to shut up, and I never do that.

Anyway, this is my favorite outfit from the week and from this post. My husband actually helped me put it together. I really wanted to wear this skirt, and I couldn't decide on what top to wear with it. I pulled out this old Fair Isle sweater, and he said that one. He was right. How cute is this outfit?!

This sweater has been in my closet for years. I'm pretty sure it came from Old Navy, but I honestly don't remember. I wear it a few times a year; it's very thick and warm, so I'm limited on the times I can wear it without dying. It's such a classic, though, and paired so nicely with this skirt. I did tuck it into the skirt, then added one of my stretchy, woven belts to camouflage the bulk.
Sweater (similar) | SkirtBoots | Socks

After the fiasco that was Monday, I wasn't in the best of moods for Tuesday, so I decided that my outfit needed to be as cheerful as possible. This colorful Fair Isle sweater was just the ticket, and I knew exactly which skirt to wear it with. Just like the sweater in the previous outfit, I've had this one for several years now. It also is very thick and warm, and unfortunately it is also very itchy, so I can't wear it without something underneath, meaning I only have a few opportunities to wear it without burning up. Regardless, it was an instant mood booster, especially when paired with this striped yellow skirt.

The skirt is part of a set that I bought over the summer. I've still yet to wear the matching shirt, and I feel like I missed an opportunity to layer this sweater over it to create a sweater-over-a-dress look. Anyway, even if I don't ever get around to wearing the shirt that came with it, this skirt has added so much fun to my closet, and I've really enjoyed styling it.
Sweater (similar) | JeansBoots

On Wednesday, I really just wasn't feeling it. I was tired and still not in the greatest mood, and I hadn't laid out an outfit the night before, so I legitimately grabbed the jeans that were on top and pulled out this comfy sweater. I added an old pendant necklace for a bit of interest, but otherwise kept everything very simple. Surprisingly, I got several compliments from students this day. Go figure.

My jeans the a pair of Levi's in a bootcut that I found on major sale at Kohl's. I can't find this exact cut online anywhere, so I linked to a pair that looks almost exactly the same. My sweater is not that old, actually -- less than a year. It's not available any longer, but Old Navy does have a similar style that I'm linking to for you.

I really enjoyed this outfit. This is the same black sweater featured earlier in this post. I told you I would get a lot of wear out of it! Once again, I layered a camisole underneath it since the stitching is more open. This go 'round I paired it with this shorter black-and-brown dotted skirt. I decided to lean into all black instead of doing some brown contrasts. Mostly because I wanted to wear my new black boots that finally came in. I got them during Cyber Monday sales for $20!

When it comes to boots, I prefer a wide calf. My legs are pretty thick, and I don't like having boots be skin tight; it's so uncomfortable, especially on days when I'm on my feet all day long. These were very comfortable for all day wear, and I was on my feet quite a bit. They have a shorter heel (around 2"), which is something I'm starting to gravitate toward the older I get. I still love my heels, but my hips and lower back can't take standing on 3-4" heels all day long anymore without consequences.

This skirt is so cute, y'all! I've been mostly wearing longer, below-the-knee styles lately, but I do love pairing knee-high boots with skirts that hit just above my knee. I layered this over a pair of leggings. They're actually the only pair of true leggings that I own. I've had them for several years, and whenever they wear out, I'll replace them with an exact pair. They're so soft, don't roll or bunch, and are affordable.
Sweater (similar) | CamisolePantsBoots

Which brings us to Friday. My students recently created and wrote about their very own Ugly Christmas Sweaters. It's a project I started last year as a low-stakes way to get us through the weirdness that happens between Thanksgiving and Christmas break. Anyway, one of my students asked if I would wear an ugly sweater with her. Of course I said yes.

I broke back out the Christmas tree cardigan that I got for last year. Other than one ornament coming loose, it's still in great condition. I layered it over a red camisole since the v-neck is pretty low on me and paired it with my Stevie wide-leg pants. These are like my Stevie straight-leg pants, which are basically elevated leggings. As you can see, they're more of an ankle length on me, which means for you tall people out there, they might be too short.

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