Anyway, welcome to the first real outfit roundup of 2026, although the first three outfits I'll be sharing with y'all are from December. If I'd been really thinking about it, I would have delayed my last roundup by a few days, but here we are.
Our weather has been so weird the last couple of weeks. We've had some cold days, but they've been few and far between. In fact, this past week our temperatures felt like early summer. It's made getting dressed very tricky, and I basically decided to stop trying to emulate winter looks in warm-weather clothes and just wear what felt good.
That's actually one of the things I've been actively working on for myself. I grew up in the 90s and transitioned into adulthood in the early 2000s, an era in which unrealistic beauty standards abounded. If you grew up during that same time period, then you know exactly what I'm talking about. I've always mostly worn what I wanted but always within these unspoken rules that dictated so-called proper proportions and what is or is not flattering.
Finding peace with my body at any given stage has been a process, and one with which I have not always been successful. But as I edge ever closer to my 40s (we're down to mere months, y'all!), I find that I'm less and less concerned with what society tells me I should feel about the way I look or dress. That doesn't stop me from questioning some of my own outfit creations, but I am experimenting more and more as I chase this version of myself that I always wanted to be but never felt like was right.
All that to say that 2026 is going to be a weird year for fashion choices as I continue to curate my closet in a direction that matches my personality. If nothing else, I hope I can inspire you to be unapologetically you.
Now for the first outfits of the year! This roundup covers the last week of my Christmas break and my first week back at work. As I said earlier, our weather has been weird, so these outfits are kind of all over the place. As always, I'll include explanations for each look as well as links to shop the same or similar items and sizing recommendations as needed.
Sizing info: I'm 5'2" and weigh about 140 lbs. I typically wear size 6 or s/m in clothes and size 7 in shoes.
We're starting with what I wore on the last Monday of 2025, and a day that I have zero memory of what we actually did. Usually I leave myself clues, but all I have to guide me for this day is a note that says, "A comfy cozy outfit for a day of errands." I don't even remember what the errands were!
These are the same wide-leg jeans I shared in the last outfit roundup. I'm so glad I took a chance with these! I really wasn't expecting to love them as much as I do. Wide-leg styles are really hit-or-miss with me, but these ones are exactly right.
Did I wear the exact same pair of jeans the next day? I sure did. Do I remember what we did this day? I do not, and once again I have no helpful hints hidden away to refresh my memory.
This sweater is everything. Not only is it a beautiful blend of bright, bold colors, but it also has that open-weave, crochet look and trumpet sleeves. Basically, it's all my favorite things in one top! Obviously, it needed a layer underneath since it's very open. I layered it over a basic, brown long-sleeve tee. It's one of the ones I dedicated an entire post to around this time last year.
That gets us to New Year's Eve. I know we did something in town, but I can't remember what. Seriously, at this point in a long break, I barely know what day it even is. I can tell you that we went to the barn, prepped some of the food for New Year's Day, and watched Dick Clark's Rockin' New Year's Eve.
This is most definitely a dated look, but who cares? I liked this outfit. It was comfortable and soft, and that's exactly what I wanted. These leggings are velour, which is not something I would typically go for, but they are so interesting. They're still available in regular sizes, but they are on clearance so if you like them, you better hurry. My sweater is one of Old Navy's SoSoft tunic sweaters. It's still available in a few sizes. My boots are still available in most sizes, and I highly recommend if you're in the market for a flat, black boot.
I wanted to look put together but be completely comfortable, especially since I was spending my morning in the kitchen. This sweatshirt dress has been a favorite since 2024, but I haven't had much opportunity to wear it this winter yet. I layered it over some plain black leggings, mostly because I didn't feel like shaving my legs.
I felt like the bottom half of this was outweighing the top half and remembered that I had this very old, thin puffer vest hiding in my coat closet. It was just the thing to balance everything out and made the outfit feel complete without adding too much warmth.
This was also the day I decided that I want to try to have fewer mirror outfit pics this year. My husband kept making me laugh, so this is what we ended up with. Don't worry. It only gets better weirder from here.
On January 2nd, I spent some time getting my office organized. I rearranged everything several months ago and never finished hanging all my stuff back up on the walls. Then Alexis and I met Chris for lunch in a nearby town at one of our favorite local restaurants.
I had an idea for an outfit and just went with it. I had this blue button-up, vest-style, ribbed top that's been sitting in a drawer for awhile that I really wanted to wear over this mesh, floral shirt, so I started there. Then I pulled out this split-front denim skirt that I've only worn once (only because I changed at my parents' house and it got left behind for months). I finished the look with these neutral Chelsea boots that I got for Christmas.
It all just felt right, even though I had never considered wearing any of these pieces together before. Honestly, I wasn't sure about it, but I made myself stick to it, and I'm glad that I did.
On Friday, we did some shopping. I don't remember what stores we went to exactly, but I can tell you that I came home with three new books, a dress, a new version of a belt I used to have when I was in college, and some new socks.
It was legitimately hot this day. So it felt like a good reason to wear my new flowers-and-coffee graphic tee. I decided to go with a flower theme and pulled out these favorite floral-print jeans.
My socks did not follow the flower theme, but only because they were only visible when I was sitting. Fun fact -- my socks are almost always fun. They'll be patterned, or textured, or have something written on them. These are old; they were were part of a Valentine-themed pack I got from Old Navy.
We're skipping a couple of days to Tuesday, January 6th. This was my second day back at work and a teacher work day. I don't usually dress up for those, but we had a two-hour training session off site so I made the effort.
This green sweater-shrug thing has been in my closet for awhile. I was really excited to get it, but then I got it and had no idea what to do with it. Then I had an idea and decided to just go with it. I layered it over a basic, black long-sleeve t-shirt and paired it with my wide-leg jeans and black Chelsea boots. I added the grommet belt because the outfit didn't feel complete. Honestly, I feel like the belt is kind of what makes the outfit work.
I'll be the first to admit that I did not start out wearing this with confidence. I wasn't expecting the sweater to be so high or for the neck to be so wide. I ended up wearing it off to one side, creating a kind of asymmetrical look...and it worked. I got so many compliments, which helped with my confidence in the look. So I guess this is me saying to trust yourself.
For my first day back with students, I wanted to re-establish that quirky, weird writing teacher vibe. I've been very into boho, grungy-fairy, academia style these days, and this feels like the perfect combination of all of those vibes.
Without overthinking it, I paired this blue flower-and-moth print skirt with this white-and-blue floral print blouse. These are two very different floral styles, but I am a firm believer that if you match the colors, you can wear any floral prints together. Even my socks are blue floral print, although you can't really see them inside my boots.
This blouse is so pretty. It's got a ruffled collar and sleeves. The sleeves are also slightly puffed, but not oversized which I appreciate. There's obviously the blue flowers but there's also white embroidered flowers as well as faux-pearl buttons. It is pretty thin, so you might want to layer a camisole underneath.
My skirt is the blue version of a brown floral skirt I shared back in mid-December. Like I said in that post, it's not amazing quality -- it's majority polyester, which isn't my favorite material for a skirt. I can get past that, though, because of the color and pattern, which I truly truly love.
I think probably one of my favorite style eras that I've lived through was the boho trend of the early 2000s. I loved all the flowy skirts and peasant blouses and interesting belts. Some of that is starting to trickle back into the mainstream, so I've been able to slowly replace some of my favorite pieces. Like this medallion belt. It was my favorite back in the day, so when I saw this one in a store recently, I could not resist. I'm honestly resisting the urge to find and buy all the boho belts.
This skirt is one of those viral flowy skirts that have been all over social media lately, just not this pattern. I absolutely love this pretty dusky pink. For this first showing, I decided to go full-on boho. This peasant blouse is one of the oldest things in my closet; I'm not even sure where it came from, it's so old. The belt just added to the overall look.
Which brings us to Friday. I'm going to be totally honest about this outfit. I decided that this was what I was going to wear the night before. I threw it in the dryer to get the fold-wrinkles out, put it on, and did not look in the mirror before leaving the house. I just trusted that it would work together.
These red-striped linen pants were one of my smartest buys this year. I wear them all the time, and they work in pretty much every season. They're incredibly versatile, which is why I just trusted that this Frog and Toad graphic tee would pair well with them. My shoes are my favorite basket-weave mary janes, which literally go with everything.
For more outfit ideas like these, be sure to check out my past outfit roundups, follow me on Instagram for weekly outfit recaps, and sign up for my email list so you never miss a new post.
A couple of notes before you leave: I'm trying something new with how I share outfits on social media. In addition to a weekly outfit recap on Instagram and Facebook, I'm going to try to share more daily outfit peeks in my stories. I'm also trying to be more timely in uploading my looks into my LTK shop (updated almost daily) as well as my Pinterest (definitely still a work in progress).
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