25 of My Favorite Outfits from 2021

by - January 09, 2022


I almost decided to scrap this post, but I put a lot of work into finding the photos and making the graphic, so here we go.

The first year of the pandemic had a profound impact on the way I dress in that it took those last vestiges of 'business casual' that were hanging around in my closet and firmly relegated them to the donate pile. Then 2021 came roaring in with much the same feel as 2020, although thankfully it included more outside-of-the-house events, even if those rarely involved large groups of people. Still, my daily style morphed once again and found a balance between casual but ready to be among people again.

Where 2020 saw me working primarily in lounge clothes and graphic t-shirts paired with sneakers, 2021 found me putting together actual outfits...many of which did include graphic t-shirts and sneakers. Ironically, only five of the outfits included in this post feature a graphic tee and/or sneakers, despite how they've seemed to take over my wardrobe.

So, I looked back through all my outfit pictures and tried really hard to narrow it down. I generally like everything I wear, otherwise I wouldn't take a picture of it! That said, a lot of my warm-weather outfits are shorts and a t-shirt, and those I rarely take photos of because there's nothing to say about them, so you'll see none of that in this roundup. Those outfits are practical because of where I live, but not necessarily my favorite.

In the end, I couldn't decide between these 25 outfits. So, out of 365 days, these are the 25 outfits I'm most likely to recreate.

Sizing info: I'm 5'2" and weigh about 150 lbs. I wear size S/M or 6 in most clothes and size 7 in shoes.


Let's start with Spring. I ordered this romper after a good friend of mine recommended it, and she was not wrong! It was probably one of my most-worn pieces during the warmer months. Sadly, it's not available anymore, but you can shop the store here.


This was one of my favorite casual blouses this year. I wore it with jeans and shorts and was looking forward to wearing it for many years to come. My cat, however, had other plans and tore a non-fixable hole in a very noticeable spot. RIP perfect blouse. You're already missed.


This pineapple shirt is so old, y'all, but it's still one of my most favorite mix-and-match pieces. And this hodgepodge of colorfulness was so much fun to wear! Pretty sure at some point I wore the same combo minus the jacket and with my yellow Converse, too, but I couldn't find photographic evidence. I have at least four of these skirts in different patterns. They're that good!


This rainbow skirt is one of the last pseudo-workwear pieces I own, and I love mixing it up in unexpected ways. This Just Peachy t-shirt is an exact color match to one of its stripes. And I'm not ashamed to admit that I ended up wearing these clear strap wedges way more than I expected to. I bought them on sale to try out the trend and expected to hate them. They work with so many outfits, and because they're strappy and have a woven wedge heel, they're not as in-your-face as some of the other clear shoes I've seen.


This dress, y'all. I've had it for awhile and it still makes me happy every time I wear it. I had never paired it with these wine-colored ballet flats before this, but they are a perfect match! This dress has the sweetest faux buttons down the front and is just so flattering. It's a classic cut, too, which means it really won't ever go out of style.


This is one of those best selling Amazon dresses that I just had to try. I actually bought it in 2020, but at the end of the summer so I think I wore it once. I made up for it in 2021, for sure! This was one of my favorite ways to style it, with a wide woven belt to accentuate my mostly non-existent waist and these favorite brown leather wedges. Sadly, it's no longer available.


This yellow-orange dress became a favorite as soon as I put it on. This color combo isn't available anymore, but there are several other patterns to choose from. It's a thicker material, which was an unexpected surprise. It's really easy to layer so I can wear it all year long, but this is by far my favorite combo. I absolutely love my denim vest.


Speaking of my denim vest, you're about to see it two more times. It's the perfect layering piece for sleeveless dresses. And this maxi dress was absolutely a favorite buy for the year. It's also a thicker material, and it has pockets!


This might be my favorite dress style from Old Navy. I just love their sleeveless tiered swing dresses. I have another one in a different print, but I couldn't find any pictures of it. This is the one I bought most recently. I loved the darker floral print, which makes it easier for styling in cooler weather. I think what I like most about this outfit, though, is the subtle print mixing with my leopard-print sneakers.


If you caught my 10 Best Things I Bought in 2021 post, then you'll know this tank top made the list. Guys, this is probably my most-worn top for the year. I love it so much that I bought another one with a different print. I was really excited to be able to pair it with this patchwork denim skirt and my converse for summer...


Then all of you guys loved when I layered it with this oversized sweater and my Chelsea boots. So, yeah. If you needed a sign to buy this tank, here it is.


I always find myself admiring people who can pull off a monochromatic look but was always scared to try it myself...until this past year when I fully embraced it. This simple sweatshirt and leggings outfit was honestly thrown together without much thought but once I added my favorite buckle boots, I fell in love.


And that inspired me to try other combinations. This one feels a little less monochromatic to me, probably because of the leopard print in the middle, but still. This tunic top is so good, though.


This all-green look was one of my favorite cold-weather ensembles, despite both my dad and husband telling me I looked like a librarian. I'm honestly not sure if they meant it to be a compliment or an insult, but considering my fall-back plan in life has always been to be a librarian, I'm not mad.


This outfit I styled showing options for leather leggings is one of my favorites that I still plan to wear in real-life one of these days. The weather warmed back up and leather leggings were out of the question. But I love the almost 50s vibes this outfit has. Something about it makes me picture Rizzo from Grease.


Speaking of Grease, this kinda has that vibe, too, now that I'm on that train of thought. Anyway, I love this outfit so much. The skirt is not the material I was expecting, but that's actually not a bad thing for where I live. It just means I can wear it year-round instead of just in the winter. It is more form-fitting, so if you're between sizes, go up.


I'm not sure why I like this outfit so much. Maybe it's the bold shirt? I don't know, but I felt really put together this day.


I never knew I needed sequin leggings in my life until this year, and this pair is surprisingly really good considering I didn't pay very much for them. They've got a thin liner so they're not scratchy. If it hadn't felt like summer on New Year's, I would totally have worn this...but with flats instead of heels.


Chelsea boots are the simple boot I didn't know I was missing from my closet. I've never really been a fan of the silhouette, but when I realized the trend just wasn't going away, I knew I needed to try a pair, and I have not been disappointed.


This was, hands down, my favorite Christmas outfit, and you guys seemed to agree in my social media poll. I'm going to figure out more ways to style this skirt to make it feel less Christmas-y though.


I can't wait to wear this outfit in real life. This skirt is so dreamy, and who knew a bodysuit was actually a good idea? Not me, I swear. But this is undeniable proof that they have a place in pretty much every closet.


I love this outfit, even if this skirt and I have a push-and-pull relationship. It's so pretty but I honestly spend all day fighting with the waistband. The elastic somehow gets folded up inside there and then the waist lays wonky, especially if I've been sitting for awhile. I still can't deny how much I like the skirt, though, waistband notwithstanding.


This outfit, for whatever reason, made me feel like a lady boss like no other outfit has. I can't pinpoint exactly why, but I felt like I was in charge of everything while wearing this.


And we're going to end with what is arguably the best sweater I bought. It's a longer length, so I can wear it with leggings if I want. But it's just such a pretty green and is so soft and comfy. I've worn it pretty much every chance I've had since I got it. And these brown Chelsea boots have quickly become a staple in my closet. They've got a little bit higher heel compared to the black pair and the shaft comes up a little higher, but they've got comfy insoles so walking in them hasn't been an issue.

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