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My 20 Favorite Outfits of 2020

December 31, 2020

Welcome to Dressed for My Day! While it’s been well over a week since I last uploaded a fashion post, those really are my bread and butter. So today I’ve looked back over the past year’s fashion posts as well as my How I Really Dressed for My Day daily outfit posts to select my 20 favorite outfits of 2020.

20 Favorite Outfits of 2020

Like many of you, I’m still growing and learning when it comes to fashion sense. I’m not an expert. I’m just a woman who has always loved pretty clothes, enjoys getting a little dressed up and doesn’t mind doing the research to figure out how to dress stylishly. Shoot. Who are we kidding? I LOVE reading up on all things fashion! I always have. But I am still a work in progress.

That’s why it really wasn’t all that hard for me to narrow this list of favorites down to 20. I don’t absolutely love every outfit I put together. Or sometimes I love the idea of the outfit and I enjoy showing it here on the blog, but it doesn’t necessarily translate to real-life style that I enjoy wearing.

For my top 20 selection I looked for outfits that…

  • resonate with my personal style aesthetic
  • are truly wearable for my lifestyle
  • pull together in a way that works for my body type and proportions
  • feature colors that look best on me and that I enjoy wearing

And in the process of culling the list, I learned a lot. I’ll share those tidbits as I list my 20 favorite outfits of 2020. These aren’t in order of preference. Instead, they’re more or less in the order that I shared or wore them during the past year. Let’s get started!

#1 – Red Pants Suit with Black Ribbed T-Shirt

Interestingly, while most of my top 20 are outfits around which I built a post rather than How I Really Dressed for My Day (or real life) outfits, almost all of them are also outfits I truly did wear. For instance, I remember the Sunday I wore this red pant suit and black t-shirt to church. Afterward James and I drove to a nearby town to shoot these photos. I remember feeling especially stunning in this combination.

5 Ways to Wear a Red Suit
See the full post for details.

I haven’t worn this suit yet this year, but it’s hanging at the front of my closet to wear this Sunday. I think it looks best with a very simple tee or turtleneck under the jacket. The suit is from Talbots last year, and they don’t have anything like it right now. But you can check out Talbots’ suiting here. They do a really nice job with suit separates, and they generally fit true to size.

What I like about it: I like the long lines of this suit on me. And I also love the stunning red combined with the basic black. Red is one of my signature colors and I wear it frequently, so I have no doubt this suit will hang in my closet for years…and get lots of wear.

#2 – Cropped Chinos with White Cotton Popover & Denim Jacket

Another thing I learned after putting this list together is that I love, love, love my denim jacket. Well, duh. I already knew that. But this list of 20 just reiterates how essential this year-round jacket is in my wardrobe.

3 Ways to Wear Crop Chinos this Spring and Summer
See the full post for details.

What I like about it: I love how these sporty but simple separates come together. I think I especially love the combination of leopard print shoes and the soft floral kerchief. It’s the little things! It will be interesting to see if these popovers are as popular this year as they were last spring and summer. I really found this one to be super comfortable and versatile. But it did take a little work to learn how to wear it.

Interestingly my cropped chinos are still available, too. I think a lot of women shied away from them last spring and summer because they’re such a new silhouette. But it looks like we’re still going to be seeing cropped and straight pants, so I think these will still get play time in my wardrobe.

#3 – White Side Stripe Black Joggers and Black Blazer

In the original post I actually styled these black joggers (similar) two ways – with the black blazer and with my denim jacket. I love both outfits. If you’re interested in joggers like these with the side stripe (so elongating!) check out the selection at

Favorite Travel Outfit Two Ways
See the full post for details.

What I like about it: I’m learning I can’t go wrong wearing black and white. Some may think it’s boring and safe; I prefer to think it’s failproof and fabulous. And I also love the juxtaposition of pairing a classic black blazer with joggers (similar). I think the key is simply choosing joggers that have a bit of an elevated look. And these wedge sneakers certainly help pull the look together, too.

#4 – Simple Green Dress and Denim Jacket

Before I could even share this dress last spring it had sold out. But I love the simplicity of this outfit, and it’s one I actually wore frequently through the spring and summer.

Featuring 1901
See the original post for full details.

What I like about it: Well, first off, there’s that denim jacket again. It’s always a winner. But I love that I was able to find a simple t-shirt type dress in one of my favorite signature colors. I think this outfit illustrates the magic of determining and sticking with your signature colors. For a refresher on choosing the colors of your wardrobe, check out this post.

I also like how the Everlane nude flats and nude tote bag work so beautifully with this outfit. I think these were wise purchases I’ll continue to enjoy. Neither are available any longer, but keep your eye on this brand for future wardrobe staples in classic lines and shades.

#5 – White Jeans + Rose Polo + Denim Jacket

This next look includes another classic purchase from Everlane. The merino wool ribbed polo is no longer available, but I have three of them. Ha! I read over a year ago that polo shirts were coming back in, but they’ve been slow to surface. But sure enough, at this point we’re seeing more of them, and I’m loving the trend.

Styling White Jeans for Spring
See the original post for full details.

What I like about it: I like the white jeans with the soft polo top and the denim jacket. Ha! Again, it’s a simple look. But it just pulls together nicely. And it’s extremely wearable. I do think the tucked top and the leather belt are integral to the success of this outfit, however. Proportions rule, ladies. Tucking in your top takes some getting used to if you’re out of the habit. But once you start you’ll be amazed at how much better your overall look is.

#6 – Cropped Chinos & Leopard Print Top & Denim Jacket

I’m not at all apologetic about showing you these same cropped chinos and denim jacket again. That just illustrates the power of carefully choosing pieces that really work for you in your wardrobe. I actually styled these cropped chinos in a couple of other posts, too. And I wore them frequently in real life as well.

Chic Spring Outfit Topped 2 Ways
See the original post for full details.

What I like about it: So, yeah. One of the things I like about this outfit is the cost per wear of the individual pieces. Everything you see here showed up multiple times in great outfits all spring, summer and even fall. And of course, I just love animal print. Oh, and this sleeveless animal print shell has been restocked. It’s also available in the 3/4 length sleeve.

#7 – Olive Green Utility Pants & Rose Cardigan

Many of my readers purchased these utility pants from Chico’s in one of the three great shades they came in. My favorites were these sage leaf green and the camel. And I styled them multiple ways from spring through fall. But I especially loved how these green utility pants paired so nicely with my rose colored cardigan.

textured 3/4 sleeve cardigan
See the original post for full details.

What I like about it: These are just good pants. They have nice lines, but also feel comfortable and functional. So I loved so many outfits I put together with them. But I think these Eileen Fisher wedge sandals really help them look especially classy. I’m surprised to find that they are actually still available in most sizes and currently 60% off. You would not be making a mistake to buy these and stash them away for the spring. These wedge sandals are extremely soft on the feet and so very comfortable. But they really elevate a look.

Here’s another shot of the same outfit, but this time I added the linen blazer. Of course, the blazer is not available, but watch for them to reappear this spring or summer.

Sweet Shades of Spring & Summer
See the original post for full details.

#8 – Simple Denim Shorts & Summer Sweater

Ahh, these photos are making me long for warmer days! I remember the day we took these photos we were visiting our son and daughter-in-law in Columbus. So maybe this outfit just evokes happy memories. But I also appreciate the casual and easy vibe of this pairing.

Denim shorts
See the original post for full details.

What I like about it: I wore these denim shorts from Talbots last summer a lot. But I especially like them paired with something other than the expected t-shirt. And I do love lightweight summer sweaters like this pretty striped one (similar). I also like the nude colored sandals and coordinating shoulder bag. Those light, neutral accessories keep the look fresh and effortless.

#9 – Flax Linen Pants & White Gauze Shirt

I absolutely fell head over heels in love with linen pants this summer. And I can’t wait to pull these out of storage and start wearing them again this next summer. These are Eileen Fisher linen pants, and event though I purchased them on sale, they were a little pricey. But price per wear I’ve already gotten my money out of them.

Elegant & Effortless Summer Neutrals
See the original post for full details.

What I like about it: I especially love how these flax linen pants worked with soft neutrals like this white gauze top from Talbots. I’m surprised to find that the gauze top is actually still available in all sizes. It was a real favorite all summer, and I’ll be wearing it again next year.

#10 – Floral & Fruit Pants with White Gauze Top

This outfit is one of four ways I styled these fruit and floral pants in the post, How to Style Floral Pants So You Look Chic and Not Childish. Actually, now that I think about it, that was one of my favorite posts of the year, too. I ended up absolutely loving these floral pants. The pants are still available, by the way, in a few sizes. I’m wearing an 8 for reference, so I’d say they fit true to size.

floral blouse
See the original post for full details.

What I like about it: Truthfully, I wore these pants pretty frequently this past summer, and most times I wore them with a plain white t-shirt. But I do love how feminine they look with this white gauze embroidered top. I also love my metallic sandals. They’re several years old now, but I wear them frequently during the summer months.

#11 – Black Lantern Sleeve Top & Chino Shorts

Have I mentioned that one of the main lessons I’m taking away from this little exercise is that when in doubt, stick with neutrals? Honestly. I like more of my all neutrals outfits than not.

Lantern Sleeve Cotton top with shorts
See the original post for full details.

What I like about it: Well, there’s those leopard print slide sandals. Love, love, love. And still available! But that silky cotton lantern top is also a winner. I think it’s just a lovely cut. It’s comfortable and looks chic and casual to me, but also a little elevated. Unexpected, I guess.

#12 – White Linen Pants + Light Turquoise Tank + Colorful Ruana

Like I said, I fell in love with linen pants this past summer. I discovered these white ones from Chico’s a little later in the summer, so I didn’t wear them quite as much. But when I did I discovered that pairing them with a pastel top produced the most cohesive and flattering look. Chico’s doesn’t seem to have any of these white linen pants left. No surprise there. But they do have the similar shorts available on final sale at a ridiculously low price.

aqua pendant necklace
See the original post for full details.

What I like about it: I shared in this previous post that when you coordinate pieces that have minimal contrast in intensity your look will be more cohesive and easy on the eyes. That’s the key to this summer outfit. I love the way the white linen pants and light turquoise top play so nicely and softly with the colorful ruana. They actually make the ruana look a little calmer, more classy. But I also love the pendant I wore in this outfit, as well as the straw clutch and those Eileen Fisher wedge sandals.

#13 – White Jeans + Black Tanks + Black Party Sandals

Brighton sent me these darling Bowie flip flops this summer and I enjoyed featuring them in this post. But I also enjoyed wearing this particular combo in real life several times.

See the original post for full details.

Once again, this outfit is built on classic neutrals. They just never serve me wrong.

What I like about it: I like that this outfit is built with two wardrobe essentials and a pair of novelty shoes. That’s such a great formula for a winning outfit. And these darling flip flops were quite comfortable, too.

#14 – Silk Blouse & Red Pumps

I knew when I purchased this ivory silk blouse that I would need to be able to wear it multiple ways to justify the expense…even though I bought it on sale. And it hasn’t let me down. I’m sharing two looks that I created with it. In this first one, I just wore my dark wash jeans, but I added my red suede pumps. Wowsa. I need to wear this sometime soon. It’s so fun.

Capsule Outfit 18
See the video for more details.

What I like about it: I love the silk blouse. Period. It’s elegant, but also works so well in casual pairings with jeans. Adding the red suede pumps elevates the look even more without compromising comfort at all.

#15 – Silk Blouse & Jeans & Nude Sandals

I wore this next outfit out for a special dinner with James and friends. It felt so appropriate for the occasion, but it also made me feel pretty and a little sexy. Hahaha! I’m not one to go for sexy very often. But these Cate Rag & Bone Jeans paired with the sand suede slide sandals just kinda create that vibe. Of course the silk blouse helps! (Similar blouse)

Style Formula #1 - Top This!
See the original post for full details.

What I like about it: I love the simplicity of this beautiful outfit. It looks effortless, but so feminine and modern and elegant. I think the keys that create that winning combination are the slightly edgy jeans with the one little rip and the frayed hems, the soft neutral sandals and of course the silk blouse (similar). The jewelry is minimal but very feminine.

#16 – Black Jeans & Cotton Sweater & Wool Ruana

As with so many of these favorites, this is an outfit I really wore. In fact, the reason my makeup looks pretty worn out in this photo is because these shots were taken in the late afternoon as James and I were returning from a little two-night getaway. This outfit felt “getaway worthy” while still feeling comfortable and casual.

leather Loafers
See the original post for full details.

What I like about it: I’m really enjoying these black straight leg jeans, so I like how they worked with the oatmeal colored cotton sweater and this plaid ruana (similar). This outfit was so comfortable, cozy, but also chic and pulled together. It felt stylish without feeling stuffy or over done.

#17 – Cableknit Sweater + Black Jeans + Plaid Top Coat

I find myself wearing this cableknit sweater often, too. And my favorite way to wear it is definitely with black jeans. But I think the cap toe slingback heels and the black courier bag really set this duo off perfectly.

Sweater Weather Outfit
See the original post for full details.

What I like about it: Again, it’s the neutrals. They’re just so effortlessly chic.

#18 – Jeans & Turtleneck Cashmere Sweater & Leather Moto Jacket

This was my first attempt at styling my new leather moto jacket (and here), and I was quite pleased with how it turned out. I definitely enjoy wearing this oxblood brown Dalby leather biker jacket with neutrals, too. But I think the deep purple cashmere sweater works beautifully with the rich tone of the jacket.

What I Bought with My Nordy Notes
See the original post for full details.

What I like about it: I like the dark wash jeans with the dark purple sweater. I also like how the boots have both brown and black in them so they blend the jacket and black shoulder bag perfectly. The intensity level is cohesive throughout, so the outfit looks easy on the eyes.

#19 – Red Skirt & Black Fair Isle Sweater

I’ve had this red wool skirt and a similar black one in my closet for years, well before I started blogging. They’re from Talbots, but I haven’t seen in solid similar skirts this year. Anyhow, I love pairing them with coordinating sweaters, tights and boots.

Skirt and Sweater
See the original post for full details.

What I like about it: I wore this outfit one day when I was out running Christmas errands – doing a little shopping, eating lunch out, etc. It felt festive and fun, but also classic and casual. I love, love, love these black boots. I wear them so often. They were perfect in the snow this past weekend. But these look sporty and chic with a skirt, too.

#20 – Red & Black Winter Classics

I’m pleased to say that I probably could have named a few more favorites, but we’ll end with this one. I just posted this outfit last week? Two weeks ago? Boy, time has become quite muddled during the holidays! Anyhow, I love this classic red and black look.

Winter Classics Look with Splashes of Red
See the original post for full details.

What I like about it: Red is one of my signature colors and black is my dominant neutral, so what’s not to love? No, really. I do love the pairing of black and red. I am a Georgia Bulldog, after all! But I think the black Blondo boots anchor this look, keeping it casual and sporty. While the red cashmere sweater (similar) and red crossbody bag elevate it.

I enjoyed putting this list of favorites together. It’s interesting how much I learned as I looked back over the year’s outfits. I learned that:

  • my denim jacket is truly a year round staple that serves me well
  • neutrals never fail
  • keep it simple sweetie!
  • shoes can make or break an outfit
  • minimizing the contrast in intensity really is an effective way to create chic looks
  • proportions are key

Thank you so much for dropping in today. I hope you enjoyed the post. I’ll see you next year!

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Blessed for My Day

Happy New Year! Are you ready for 2021? I guess we’d all like to begin a new chapter after the year we’ve had. But while the calendar indeed turns, many things will undoubtedly continue to be different for some time yet. I think something in most of us expects everything to be fresh and new on January 1, while we really know better deep inside.

But while circumstances may not change much for a while, we can be assured that God is indeed doing something new. He always is! God is always at work around us and in us. He is making us new…more like Christ. And He is preparing for us a new home, too. While circumstances may not change for a while, we can indeed look toward the future with hope and anticipation. Not because things will change, but because God is at work.

Behold, I am doing a new thing;
    now it springs forth, do you not perceive it?
I will make a way in the wilderness
    and rivers in the desert. ~ Isaiah 43:19

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xoxo, Kay
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23 thoughts on “My 20 Favorite Outfits of 2020

  1. You left out my favorite outfit 🙂 I loved you in the pink coat from j.crew. Sadly it was sold out when I went to purchase.

  2. That was fun, Kay! So much inspiration! My favorites were numbers 1, 3, 4, 6, 12, and 18. In fact, I have “shopped my closet” for most of those looks Thank you! May you have a Happy New Year full of hope and joy!

  3. I love so many of these looks, but 5, 7 and 19 are my favorites. And I’m one of your readers who bought the Chico’s pants…in all 3 colors, and I never do that. ? Thanks for the inspiration and all the work you put into your posts, Kay. I wish you and all of your readers health and happiness in 2021.

  4. Great post, Kay! Thanks for the year in review. My favorite looks are 1,2,4,6,7,8,12, 16, and 20.
    Happy New Year to you and your family,

  5. I love my fitbit. My husband bought me a Versa 2 last year for Christmas. It really helps me to move each hour (I work at the computer all day – teaching on line – and I forget to get up and move.) Also, if I am near my goal for the day, I will walk around the house until I hit my goal; this cracks my husband up. I also like putting in my activity (yoga, strength training, abs), and I aim for 3 days a week so when I surpass that, I am pleased with myself.
    Of the outfits here my favorite is the white jeans and black top; black and white are such crisp, classy colors, and one can add great accessories.
    Have a wonderful New Year! Looking forward to your posts and inspiration.

  6. Hi Kay…..all the looks are so great, I can’t pick a favorite!

    Will you be letting us know what is on trend for spring/summer? Wish we could go somewhere to show off our style…..hopefully sometime soon??

    Blessings and Happy New Year to you and James…..enjoy your visit with your daughter?

    1. Hi Holly. I’m glad you enjoyed the post. Yes, I’ll definitely be sharing spring/summer trends and colors in a couple of months. Probably as early as February.

  7. Happy New Year, Kay
    Great post today! My favorites are 2,5,6,9,13,17. I have learned so much from you through out 2020. Your style is so much like mine. And my wardrobe has changed for the better!!! I so look forward to your blogs and videos in 2021! Wishing you and your family a blessed and healthy new year.

  8. I just loved seeing your list of top 20 favorite outfits. I certainly had my favorites that I would wear. I am still struggling with picking my signature colors because I like color and want them all. But I see your point that it really helps in having a pulled together wardrobe that would really be more versatile. I really liked reading your reasons for liking each outfit. One of the reasons I like your blog so much is how much you add commentary. I really have been learning from it. One thing is the color intensity, before my eye wouldn’t like an outfit I put together and I couldn’t figure it out. Well now I see a lot of the time it was that, and I can change it pretty easy now that I know/understand the problem.
    Looking forward to next years posts!

    1. I too have struggled with picking a signature color and have lots of colors in my wardrobe. To have a pulled together wardrobe, what works for me is focusing on one color each season (fall/winter and spring/summer) and then doing another color the next year. This fall/winter I have been working on filling in the brown section and purchased shoes, a blazer, a pair of pants, a novelty sweater, and a cashmere sweater that work together and with other things already in my wardrobe. Next fall winter I may focus on red. This spring/summer I plan to focus on pink.

  9. Pasting these four principals on my closet door so I don’t forget.

    resonate with my personal style aesthetic
    are truly wearable for my lifestyle
    pull together in a way that works for my body type and proportions
    feature colors that look best on me and that I enjoy wearing

  10. Oh, what a fun post, Kay! I think I’m going to say my favorite outfit is #19, probably because I ordered that black Fair Isle sweater just yesterday! 🙂 It looked so pretty in your video that I just had to check it out! It was on DEEP markdown and I got a special bonus for joining the rewards program. I can’t wait for it to arrive. I might just try to ‘copy that style’ but I’ll have to find a red skirt, first. Ha!
    Happy New Year!

  11. Love the red pant suit… so classy. But, confused, you said you wore it to church one Sunday and James made pictures later that day. And then in next paragraph you say you haven’t worn it this year but it’s hanging in the front of your closet to be worn. I’mmm easily confused?

    1. Hahaha! I guess I mean I haven’t worn it this winter. I wore it and took those photos last January. Thanks so much for reading, Judy. ?

  12. My FitBit is a game changer for me! I actually find myself playing mind games. If it “tells me” I haven’t yet been active in an hour, I’ll tell myself, “ it only takes 2 1/2 minutes to walk that 250 steps. Let’s go for five minutes!” I’ve also been known to “allow” myself to watch a 30 minute show, as long as I walk for that 30 minutes! Have fun with it!

    And a random post idea because today’s was so good: would you consider posting a few of your least favorite real life posts and tell us why they didn’t work for you? I learn so much from you!

    1. Hmm. Great idea for a post. I can definitely do that. Yes, we’re HIGHLY motivated by the Fitbit challenges. Hahaha! It’s doing me a world of good already. I’m so very guilty of sitting for hours at the computer. But I’ve discovered that a trip down my little road and back is just over 250 steps. And I have basement stairs I can use to get those in too. So I think this is really going to help me.

  13. I really enjoyed this post Kay! I cannot pick my favorites. I have a good denim jacket and the Chico’s pants in two of the colors that I have struggled with. When I try to pair one of my signature color tops with the pants, I just don’t like it. I need to try harder this Spring. And as much as I like my denim jacket, I never reach for it, and I honestly don’t know why. Needless to say, I have need to spend time in my closet creating outfits and eliminating pieces that I can’t make work for me, no matter how popular they are. Loved the BFMD! Happy 2021 to you and your family!

  14. I love my Fitbit Charge 4. I got it for my birthday this past year. Check out the bands you can get for your Fitbit. I have different bands so I can coordinate my Fitbit band with my clothes. Also, get the screen protector. I have one that is a hard cover. It really does protect the Fitbit. I ran up against a brick wall and the only damage was to the hard shell protector. My husband likes how the cover makes my Fitbit look like a watch.

    1. Hi Cindi. Yes, we’ve already got some new bands for my Fitbit. I like the way it elevates the appearance of it as well as how it feels more comfortable. Thanks for sharing about the screen protector. I’ll check into that.