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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 C 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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33 thoughts on “My 25 Favorite Outfits From 2020

  1. Not sure your tech issues are solved. I did not receive your news letter in my in box today. I get it every single day but had to go to your web page to read your blog today. Not sure if it’s on your end or not. Will depend if other’s didn’t receive it either. Just giving you a heads up. I received everyone else’s post today, if that helps.

    1. That would be a different tech issue, lol. The email issue was with my blog comments getting emailed. However, if you still don’t have my email newsletter, let me know. It went out a little later than usual this morning.

  2. SO many great outfits and oodles of inspiration!! Can’t wait to see what’s in store for 2021! Oh, and I received your email today. Have a wonderful day!

  3. Hi! It’s always interesting to read (and see) what you favour the most out of all of the outfits you create for the blog. Thank you for a wonderful year of fashion.

  4. I loved looking back with this recap of the year of favorites. Thanks for taking time to do that. I so appreciate your sharing of how things work together. That is so helpful to me. I also love how you have said here and there about this works with my body type it gets me to remember that I need to think about that too. I sometimes go shopping and am drawn to something that looks good on a hanger but not on me. 
    I just went through my shirt section of closet and paired down. I am going to copy you and not add any more hangers. If I buy any more things I will donate something to make room. 

  5. Almost all skinny jeans with some kind of sweater and jacket… You definitely have a uniform/favorite look.  Thanks for the wrap up–here’s to new beginnings in 2021!

  6. Thanks for taking the time to do this summary and giving us inspiration.  I really do love the Nordstrom front drape faux sudden jacket (look #9).  The black t-shirt with taupe shorts and snake print sandals is another fav of mine (look #7).  Looking forward to more inspiring looks in 2021!  Yay to graduating from chiro!  Maybe make an appt for 2 weeks from now for a “tune -up” so that you stay on top of things maintenance wise?  Here is looking to a kinder 2021 for us all. 

  7. I have been following your blog for a while and always enjoy your honesty and transparency. This isn’t related to this post, but would you mind giving us an update on your way of eating? Are you still doing OMAD? I’ve been doing 5:2 since the summer where you eat regularly for 5 days and limit calories to around 500 on two days. It’s been tougher to stick to during the holidays, but I’m buckling down and getting serious again.

    1. Sure, I’m still doing IF but not OMAD. I usually have a lunch or a snack as well as dinner, and often another snack in there somewhere. Over the holidays, I’ve been more lax with length of fasts, and also with how much crap I’m eating, lol. I’ve put on a few pounds, and I’m trying to buckle down and get back to 19:5 and cut out some of the crap.

  8. You always look great! I’d be hard pressed to find 25 pics of myself in complete outfits this year… 🤣
    On look #22 – the booties- the cloud color you’re wearing was sold out previously so I ordered the darker suede color. They are beautiful but I haven’t worn them yet. Which color is more versatile or do I need both? Lol! I don’t have gray boots. Is the cloud color basically like wearing gray? I had ordered the black leather too but they were too hard to get on. The suede are easier. 

    1. I love the taupe suede ones too! I think I had them at one point, and I had the Vince Camuto ones in Tortilla Suede, and then I realized I have other Vince Camuto boots in Tortilla Suede, so I changed those for Tuscan Taupe, and I changed these for Cloud Suede. 😂

      All that to say, I think these in the darker color are awesome and highly versatile. I personally wear that color more than this one. This is very light. But if you have budget and closet space for both, there’s no shame in that game. #shoppingenabler

  9. I like all of your outfits in this post!  There are a few that really catch my eye for various reasons.  I wish I would wear my denim jacket.  I hardly ever put it to use, which is so frustrating because I see from you how it can amp up an otherwise okay outfit.  I hope the chiropractor released you today!  Guess where I am?  Yes, in one of my deer stands.  It’s been a warm and beautiful day here ahead of the stormy weather moving in for New Years Eve & Day.

  10. I have a challenge for you:  What about doing a post of nothing but outfits that now you don’t like?  Reading what you don’t like would be a great learning for us!

    1. What a great idea! I think it would be really helpful to see why something might not work.

      Loved this post, btw…so many really great outfits. The black with the tan suede jacket is one of my favorites. Unexpected, but very eye-catching.

  11. I really like these posts, but what struck me this time, maybe because it shows outfits over the course of a year, was how many times I thought to myself, “I bought that”.  Probably most outfits show at least one item I have. I finally found 2 items recently that have been out of my size for a long time. But I remembered once you said you stalked an item like it was your job, and finally got it. So I began to do that also and usually eventually find it. Two recent finds were the Good American jeans you love so much, and the hooded leather jacket shown in this post. Both had been out of my size for a long time, but I continued to check back. But neither one has arrived yet, and they both shipped awhile ago. I heard things are getting hung up so hopefully, I will receive both this week. Today I ordered the Vince sweater that is NOT cashmere, with the v-neck, but the only color in my size is camel. I think I will love it. And you looked great in these pictures!

  12. #7 and #22 are MY favorites….and yes, I did copy both!!! And love the looks!

    Once again, Than you for keeping me feeling terrific.

  13. Just today ordered the Vince Camuto Jean jacket you posted. Great sale and I missed the last sale messing around deciding. You always look so great in it and the color seems to go with so much. My dark one doesn’t and I never wear. It’s from Loft years ago and looks brand new. Hoping to wear my new one lots this Spring. Your outfits always look so put together with it. I ordered the XS and small to compare. Maybe a post with various way to wear a jean jacket? Maybe it’s a no brainer but some new ideas would be great. I miss seeing people wear scarves. I feel funny wearing mine now. It use to be a daily thing for everyone. Love scarves. 

  14. FYI  If you or anyone else is looking for a great pair of slippers, I ordered the Leopard print faux fur (closed toe) slippers from LOFT in Nov. and just got them late in Dec. and I LOVE them. They are so comfortable and well made and the leopard print is more cool toned, which I like.  They are currently 60% off plus an extra 30% off. Hope the shipping isn’t as delayed for you as it was for me.  I had other LOFT items come before they did.  

    1. I just snagged the mini cheetah jacket in small…Yay! Thanks for the tip alerting us that it is available again!

  15. Happy New Year! I’m glad you included the leather jacket with the hood in your favorites. I have wanted a leather jacket to replace my faux one and have been stalking the Nordstrom site for that jacket in a small with no luck until yesterday. I seized the moment, placed my order, and did a happy dance!

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