My 25 Favorite Outfits From 2020

Last year, I set out to create a post with my 10 favorite outfits from 2019, but I ended up with 20, and I said I could have easily come up with 30.

This year, I set out to do the same, and before I started whittling them down, I had almost 40! For a year of going almost nowhere, I’d say that’s pretty impressive, but I did narrow them down to 25.

I kind of surprised myself by choosing more outfits from my What I Wore Lately posts than I did from my dedicated outfit posts. Sometimes I’m drawn to the photography or the setting more than the actual outfit, but for this post, I tried to choose mostly outfits I actually wore in my daily life.

That means a lot of them are similar. When I come up with an outfit formula that works, I often repeat it over and over with different variables, don’t we all?

And of course, there are a few wardrobe items that get repeated over and over. While that may seem boring or redundant, I like how it demonstrates the concept of cost per wear. So anyway… let’s get started!

MY 25 FAVORITE OUTFITS FROM 2020

#1. Last January, I wore this outfit to a Phil Phillips concert in Philadelphia. That was one of my Christmas presents from Paul.

I wanted an outfit that was a warm, chic, a little edgy, but not try-hard. I think I nailed it.

The donegal pattern in this black sweater makes it just a little bit more special than a basic black cashmere turtleneck, but unfortunately, they don’t offer that color in the turtleneck this season. A  quick Google search didn’t turn up one anywhere else either. If you know of one, let me know.

similar leather jacket // turtleneck // jeans (on sale) // boots // similar belt // earrings // bracelet

#2. Yikes, my feet are pale, but not that pale! (And no, I was not wearing hosiery.) The light must have been reflecting off the cement.

This was a Valentine’s date night look I put together for a style collab with two other bloggers last February. I never wore this exact outfit anywhere, but I love how it came together. It’s a bit unexpected —  a pink suede jacket over an all black look, but I think it works.

similar jacket // tank // similar jeans // pumps // necklace

#3. Admittedly, not the most inspiring outfit of 2020, but probably the one I’ve worn the most… There’s something about the combination of light neutrals and the simplicity of this look that is so pleasing to my eye, and this sweater has the perfect v-neckline.

sweater // similar rag & bone skinnies // sneakers // necklace // earrings

#4. Moving into spring, this blouse was on heavy rotation, as were these jeans. I love the color combination and the silhouette of the blouse with the narrow v-neck, flutter sleeves, and fitted but relaxed shape.

blouse (on sale) // jeans (on sale) // sandals (only avail in white) // earrings // necklace // bracelet

#5. This look is very similar to the one above, and I almost didn’t include it for that reason, but it’s one that I wore a lot in various iterations. (I had this blouse in solid pink as well.) It has a similar silhouette to the one above, which seems to work really well for me.

And then these jeans are the AG Farrahs, which I love so much and have in several washes. They’re currently on sale right now, and I find them true to size.

blouse // jeans (on sale) // flats (on sale) // pearl earrings // necklace

#6. Of course, we spent most of the summer at home, but we hosted some small gatherings outside in our backyard.

I love the beachy/nautical vibe of this lightweight sweater paired with the crisp white shorts and minimalistic (minimalist?) thong sandals.

sweater // cami // shorts // sandals // earrings // bracelet

#7. Once restaurants opened up, we ate out a lot, and it was usually hot so I ended up wearing shorts a lot more than usual.

I love this black/taupe color combo and how the snake print sandals pull it all together.

tee // shorts // sandals // sunnies // similar earrings // bracelet

#8. This dress was an #NSale purchase, and I wore it to church a few times. My wedge sandals are a few years old, and the dress sold out, so I can’t link anything here. I still wanted to include it though — I think it’s the only dress in this post!

#9. I really started embracing the fashion sneakers this year. I would have most definitely worn ankle boots with this look a year ago, but now I’m loving the combination of the jacket/tee/jeans and sneakers.

draped jacket // white tee // similar jeans // sneakers // necklace // earrings

#10. As we move into fall, about half of my favorite outfits involve these jeans. The faded black wash goes so well with everything, and it’s not as dressy as jet black jeans but looks more pulled together than blue jeans.

I wore this outfit out to dinner one weekend in September. I love the combination of camel and off-black, and the way the leopard shoes pull it together. And this necklace is the perfect statement piece to draw the eye back up towards my face.

camel sweater // black jeans // leopard flats (size up) // necklace // earrings

#11. At one point I had 3 or 4 outfits with joggers and a denim jacket in this post, but I forced myself to pick two. I chose this one because I like the added interest of the graphic tee.

tee // denim jacket (on sale) // joggers // sneakers

#12. And I chose this one because… I dunno, I just love every component of this outfit.

This tee is supremely soft and has such a good classic fit, the Vuori joggers pair so well with these P448 sneakers. The denim jacket needs no introduction at this point.

I wore this to travel to Massachusetts when Caroline and I went on a college visit back in November.

denim jacket (on sale) // grey tee (M) // joggers (also at Nordstrom; size M) // sneakers // earrings // necklace // bracelet

Speaking of the denim jacket, I have a kajillion outfits I love wearing this thing…

#13. I wore this outfit to church one Sunday in September.

Again, I used animal print shoes to pull the colors of the outfit together. I’m shocked these mules are still available. They’re on sale too!

rust tee // denim jacket (on sale) // jeans (on sale) // mules (on sale) // earrings // bracelet

And then there was that cheetah tee… I’m so very sad this sold out and isn’t available anywhere else.

The slub jersey schoolboy crew neck tee, however, is a staple in the ATM collection, and it’s available in lots of solid colors. Pricey, but very well made, and a classic you can have for years.

And I found a similar for less version of the cheetah print at Amazon.

#14. I paired it with black raw hem skinnies and topped it off with my denim jacket for a casual fall look.

cheetah tee (similar for less) // denim jacket (on sale) // black jeans // mules // sunnies // earrings // bracelet

#15. The cheetah tee pairs beautifully with those off-black Good American jeans as well.

I love how the studded pointy toe mocs and the belt with the silver buckle elevate this very simple outfit, and the quality of these pieces keep it classy.

cheetah tee (similar for less) // jeans // similar belt // flats // bracelet // similar earrings

#16. And when I top it off with a black leather moto, it takes on a more edgy, rock-and-roll vibe.

cheetah tee (similar for less) // leather moto (on sale) // jeans // flats // similar belt // similar earrings

17. This is one of those outfits I debated including in this post because I can’t decide if it’s the look I love or the photography/background/fashion blogger walk that Alison nailed with this picture.

Nevertheless, I do like how the muted rust/pumpkin-colored scarf becomes the focal point of this otherwise neutral outfit. It’s such a pleasing color combo, and the wall behind me sets it off perfectly.

sweater (on sale) /similar leather jacket // scarf (on sale) // jeans (on sale) // boots // sunnies

Speaking of pleasing neutral color combinations and quintessential fashion blogger photos…

#18. I absolutely love how this outfit came together, although it is one that I never actually got to wear anywhere.

Jo-Lynne Shane wearing a taupe suede moto jacket outfit for fall

suede moto // tank // jeans // booties // similar belt // necklace // earrings // sunnies

#19. I tried to recreate a similar vibe for a dinner out the following month, but I wanted to incorporate a sweater for warmth.

I topped it off with my suede taupe moto, but I removed it inside the restaurant.

suede moto // similar sweater // grey jeans // similar pumps // necklace // earrings (old)

#20. I love an all black outfit, and this is what I wore for Thanksgiving. I probably have other all black outfits that are more interesting, but this one caught my eye as I was scrolling through.

I like the unexpected short-sleeve sweater and the pattern and bling from the bracelet, and of course those swoon-worthy studded flats always elevate a casual look.

sweater tee // jeans // flats // bracelet // earrings

#21. And there’s really nothing special about this outfit, except I just love it for its simplicity, and the fit and proportion. I feel like it makes me look long and lean. #yesplease

sweater // jeans // boots // necklace // earrings

#22. Once we get into wintertime, I start to tire of the earth tones and neutrals, and I love to break out my white jeans with a fresh, bright color or a frosty pastel. I wore this outfit to church a few weeks back.

These boots in the Cloud Suede are perfect for pairing with white jeans in the fall and winter. The low contrast creates a long, lean leg line. They’re also on sale!

blue turtleneck // white jeans // booties (Cloud Suede; on sale) // pearl earrings

I’m throwing this next one in here out of order because I’m too lazy to go back and re-number. It’s one I really wanted to include, and now that I’m nearing the end of the post, I have room for one more to make 25 total outfits. That seems like a good round number! Except it’s really an odd number, but I think you know what I mean.

#23. I love the combination of light neutrals and the overall proportions of this outfit.

I am also super excited to tell you this jacket is fully stocked and on sale at Evereve!!! It was sold out everywhere for the longest time. It’s even less at Nordstrom Rack, but sizes there are limited. It’s also on sale at Nordstrom in the sage at Revolve in the pink.

Rails Collins utility jacket in mini cheetah print at Evereve and Nordstrom Rack; also in sage or pink // white tee // similar jeans // mules // earrings

#24. This is similar to the outfit I wore for our family pictures, but I like this version a little better. The combination of grey, black, and oxblood is one of my winter favorites.

similar leather jacket // grey turtleneck (similar for less) // jeans // boots // earrings // sunnies

#25. I’m ending with one of my favorite looks AND photo shoots from the year. I realize the outfit is super similar to the one above, but I guess that just shows how well it works!

And again, I’m loving the fashion sneakers as an alternative to ankle boots. Either would work with this look, but the sneakers make it a little more modern and fun.

Luxe Meets Sporty: A Casual Monochromatic Outfit for Fall

similar leather jacket // grey turtleneck (similar for less) // jeans // sneakers // earrings // sunnies

Aaaaaand, that’s a wrap! I’m off to see my friendly chiropractor… I’m thinking he may discharge me today. I’m feeling much better. Have a terrific Tuesday!

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