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My 22 Favorite Outfits of 2022

Building a Wardrobe
December 27, 2022

This week I’m sifting through my analytics here at Dressed for My Day to see what resonates with you, but I’m also reflecting on what has resonated with me this year. While I try to do the research and be a resource for you in all things fashion for the woman over 50, in many ways this blog also serves as a diary of my own personal journey to build a wardrobe that works for me. So I looked back through all the photos of the outfits I’ve worn this year to decide what I liked and what didn’t really work for me. And today I’m sharing my 22 favorite outfits of 2022.

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Today I’m not just sharing my favorite outfits from the past year, but I’m also sharing insights I gained from this little exercise. It’s actually been quite enlightening to look back over these outfits. In fact, I highly recommend it if by chance you have taken mirror selfies over the past year.

While I have styled a lot of outfits for here and on the YouTube channel, I only allowed myself to select my 22 favorites from the outfits I really wore. So many of these are mirror selfies while others are photos James took and we featured here on the blog, but I do know that I wore these specific outfits, often more than once.

Favorite Shorts Outfits of 2022

I’ve categorized these outfits just so we can compare apples to apples and oranges to oranges, so to speak. But keep in mind that I really lead a very casual life. I work from a home office, attend a very informal home church and do very little that truly “requires” me to dress up. That said, I do like to dress up, so I almost always pull an outfit together and occasionally go all out.

My first set of favorites are shorts outfits I wore this past year.

Denim Shorts with a Linen Shirt & Tank
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I do still enjoy wearing denim shorts occasionally, and when I do I like for them to be at least mid thigh length. In fact, this is about the length all three of my favorite shorts outfits landed at. I like wearing sleeveless tops in the summer, but generally like to add a linen shirt over them. In fact, I just now noticed that in all three of the shorts outfits I selected I’m wearing or (in the last photo) carrying one. See, that’s the kinds of intel you gain with this sort of exercise. Very helpful going forward!

With a Tank and Linen Shirt
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I also noticed that, while two of the outfits I chose do feature some color, the colors are subdued and soft in these shorts outfits. I think those choices very much reflect my personal style and I’m going to lean into that as I select pieces to add to my wardrobe this spring and summer.

Linen Outfit for Summer
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And finally I noted that my footwear choices in all three outfits were nude or metallic sandals. The Born sandals and Tory Burch Miller sandals in the first two outfits have been in my closet for at least two seasons or more. Tory Burch gifted me the gold Miller Cloud sandals this summer, and I loved wearing them. So as much as I like the idea of colored sandals, I think that nude and metallics are my preference.

Favorite Jeans Outfits of 2022

Next we’ll move on to jeans outfits, which turned out to be a very eye-opening category. Turns out I don’t always like the outfits I create with blue jeans, so that’s something I’ll be working on this next year. But I really liked the way I styled my black and grey jeans. And you’ll not find a single outfit here with white jeans. Honestly, I don’t think I wore them much this past summer.

Friday Afternoon
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The outfit above would have looked nice with white jeans, too. But I think I preferred the black because they’re a little more slenderizing on me. Pardon the dusty mirror above. That happens sometimes. Ha!

There are a few items you’re going to see over and over in these photos, and that silk blend ribbed polo from J.Crew is one of them. I had all three colors and wore them on repeat. Love, love, love. The ribbed polo and ankle length jeans became quite the style formula for me this year. And then pretty often I added a blazer over that duo.

What I wore Wednesday
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Above and below you’ll see a style formula I used a lot this past year, too: one color for the bottoms and a different color for the top and jacket. I think this formula looks so cohesive and easy on the eyes.

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Below is an outfit with about as much contrast in intensity and colors as I ever allow myself. I wore this Veronica Beard Miller Scuba Jacket (no longer available) in a lot of my favorite outfits of 2022. I really enjoyed wearing black, white and camel together this year.

Black Jeans and Camel Blazer
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Below is another outfit with that I really love with that jacket. I had taken the Miller jacket as my only jacket to the LTKCon, but hadn’t really planned or even thought to wear it with this black jeans and black print top combo. But it was chilly in the conference hotel, so I returned to my room and put it on. Voila! Turned out to be my favorite outfit of the week and one of my favorites of the year. The dark black jeans above and below are my Veronica Beard Ryleigh jeans. And the lighter wash black jeans above are by Frame (similar).

Meetings and Sessions
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Of course, another thing I really like about that outfit above is the chunky gold chain necklace. That turned out to be a favorite accessory this year for sure. And those Sarah Flint pumps really elevate the look, too. Ooh! and that caramel and black shoulder bag has been such an outfit making accessory this year, too. It was a Nordstrom Anniversary Sale find.

Grey Jeans and Beige top
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Next up, I have several variations on this grey jeans outfit. In this first photo above I’m wearing the Fidelity Denim Katie Surefires. They’re a full length bootcut jean. And below I’m wearing my ankle length Mother Rider Skimp jeans (no longer available in this wash). I’ve really enjoyed both so much. And recently I added these Gap Sky High Vintage Slim jeans in grey (not shown here) to my wardrobe. I got the tall fit in those, so they hit me below the ankle. Of course, those Gap jeans are at a much lower price point, but I like them just as much as the others.

Grey Jeans and Ecru Top
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I’ve just really enjoyed wearing grey jeans and oatmeal colored tops as well as camel tops or jackets. Such a fun and interesting color combination and I’ve worn it a lot this year.

more economical option
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The outfits above and below are pretty much the same I think, but I wore them on different days. Those Vince square toe slide sandals turned out to be a favorite shoe for these combinations.

Wearing Camel and Grey for Fall 2022
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Below I’m showing another grey jeans outfit I really enjoyed wearing. This particular day I wore the white North Face jacket over the Rails seersucker plaid button up shirt and my Fidelity Denim Katie Surefires to Bible study and then lunch. Oh, and I’m wearing this grey and white striped tank underneath. I really love this layered style.

What I Wore to Our Last Bible Study
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The grey jeans outfit below is a little different than the ones above because I simply paired the jeans with a light pink cashmere sweater. I really like how grey jeans work with pale colored sweaters and tops. And I think that this year I finally began to get a grasp on low contrast in intensity dressing, which is ideal for my coloring and intensity levels.

Thursday for LIVE
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Another thing I did in several of the outfits above is mix my metals. I found that, especially when wearing grey and camel, it’s smart to wear a little bit of silver and a little bit of gold jewelry. And I would combine those pieces by wearing one or two pieces that were mixed metal, like these earrings shown above.

How to Style this Plaid Blazer Now
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The only two outfits in my top 22 with blue jeans are above and below. And honestly, I’m pretty over the ripped jeans I think. So I haven’t been wearing the jeans above any this fall or winter. But I do like the way the overall outfit looks above. I wore that one last winter. I really like the combining of the floral print silk scarf (similar) and the plaid blazer.

Work from Home First
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I just really made a point to give button up white shirts another shot this year. I wore them several times, but I think the look above is my favorite. Maybe that’s because I also really like those little mules. So fun! But I also think I did a good job of accessorizing that simple combination to elevate it a bit.

Favorite Corduroy Pants Outfits of 2022

Who’d of thought I’d need a whole category for corduroy pants? Ha! But I do enjoy wearing Talbots’ straight leg cords, and I’ve got several pairs by now. I wore these navy ones with a dark green v-neck sweater and my Sorel booties last winter.

My Daily Outfits - out to lunch and shopping with Abby
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And the outfit below seems a little out of place among all these outfits comprised mostly of solids. But I just really remember feeling pretty that day. Of all things, I was going to the dentist. But the outfits felt warm and fall-festive.

What I Wore to the Dentist
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I’ve probably enjoyed my red corduroys more than any of the others this fall and winter, and the outfit below is undoubtedly my favorite way to wear them. I’ve probably repeated this dark brown and red combo at least half a dozen times.

Red and Brown for Thanksgiving
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I really got on the brown wagon this fall, and I think wearing it with red is so fun and a little unexpected. Maybe that’s one of the things I’m learning about my personal style: I like to create color combinations that are easy on the eyes, but also just a little out of the ordinary.

Favorite Linen Pants Outfits of 2022

Now here’s a sweet spot for sure. I love me some linen! I do reserve mine only for summer, not because you have to, but because I just want to. It’s just one of the little ways I celebrate summer! The linen pants in these first three photos are the Frank & Eileen Italian performance linen ankle pants. I’m aware that they look very casual, but that’s how I roll most days in the summer. And that’s exactly how these pants are supposed to look.

What I Wore to Church
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These rather pricey linen ankle pants do come in other colors, and I think I may invest in one other this spring. Probably either the black, navy or sage green. They’re just extremely comfortable and easy to wear, featuring a high rise waistband, a slightly stretchy fabric and a raw edge hemline. And as much as I like them with the pink polo above, I really prefer them with the oatmeal beige polo below. So cool and fresh looking to my eye.

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And below I’m wearing them with this black cropped length polo and these black sandals. That’s another fun, sporty, and very casual look.

Black Polo and White Linen Casual Pants
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I went through an Eileen Fisher phase, but I think I’m mostly over it now. I do still like her clothes in small measure, but I think I fare better with clothes that are at least a little more fitted than many of her designs. That said, I do like the linen lantern pants and oversized linen blend sweater below. I think that Coastal Grandma look is so soft and a little romantic looking. And very comfortable and fresh for a hot, humid day…which that day in Indiana was! (You can tell by my thick bushy hair. Ha!)

Coastal Grandma
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But my favorite linen outfit of all is the one below. In fact, this just may be the outfit of the year. If I could wear this simple but sharp combination of flax colored linen ankle pants, a simple white tee and a white linen blazer every day? Yeah, I absolutely would. I think we took this photo on Mother’s Day this spring, and the outfit felt absolutely perfect for the day.

Linen Pants
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I also remember that those sandals were surprisingly comfortable and wearable. I love how the top half of the outfit is white and the bottom half is oatmeal beige. Such a soft pretty combination.

Favorite Dress Slacks Outfits of 2022

And to wrap up the pants, let’s check out my other favorite dress slacks outfits. I wore this navy slack combo last winter. Once again, I love that floral silk scarf with the plaid blazer.

Stretch Your Wardrobe By Planning It
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Below I’m wearing two coordinating pieces from Veronica Beard. This is the Miller Dickey Jacket in navy with gold buttons (it comes in silver button and black fabric options, too) and the Renzo pants. Since I don’t work in an out-of-the-home office or have a lot of meetings to go to, I didn’t wear these separates a lot. Well, I didn’t wear the pants a lot. But when I did, I loved it!

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The combinations are endless with those suit-like separates. Here I’m wearing them with an old shell from Talbots and my Ally pumps (use code KAYHEELS for $40 off your first pair of heels and KAYFLATS for 10% off your first pair of flats at Ally).

Here’s another look with that beige polo top and a blazer. This time I’m wearing the flax colored linen blazer. And I’m wearing that duo over some ankle length black demi boot pants from Talbots. I do wish those pants were a little longer, just a touch. But I think the nude heel makes them work just fine. And I really love the combination.

What I Wore Sunday
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Below I’m wearing the Talbots Glen Plaid Hampshire ankle pants. These turned out to be a surprise favorite. I’ve enjoyed wearing them several ways, actually. But I felt especially on my game when I wore them to the UGA AdPR job fair (where I met our assistant Lucy!).

What I Wore to the Career Fair
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But for a more casual look, I did also add the combination below to my top 22 favorite outfits list. This is more “where I live,” so I definitely appreciate the way the Glen Plaid Hampshire ankle pants work with my plain black polo and black lug sole loafers.

What I Wore to Church
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And then these red Hampshire Ankle Pants also turned out to be a surprising favorite. I thought I was done with colored pants, but nope. These are such a pretty red, and the Hampshires are just fitting me really nicely lately. And I love pairing red and camel again.

How to Look Classy in Colored Pants this Winter
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By the way, I show and wear my more expensive Ally and Sarah Flint pumps a lot, but those above are neither. They are these Nine West pumps from Kohl’s. And they are great shoes. I actually prefer them when I’m wearing camel like this.

Favorite Skirt and Dress Outfits in 2022

And yes, Virginia, I do have some skirts and dresses. Well, I have one skirt. Hahaha! Worn several ways. I purchased this accordion pleated skirt from Ann Taylor last winter and challenged myself to style it for every season. And I absolutely met the challenge.

Styling a Pleated Midi Skirt for Winter
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Above I styled it for winter with my camel sweater, black boots and black leather blazer. So sharp! And below I styled it for the winter another day with my black sweater and cap toe flats.

What I Wore Wednesday
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I love that classic look! And below I styled it for winter with a different camel sweater and boots. So I wore this skirt A LOT! And I think that’s how skirts work best for me…one…styled multiple ways. Skirts overwhelm me a bit. So I think the key was finding one that worked for me silhouette-wise and then “mastering it” by forcing myself to style it over and over.

My Daily Outfits for a Cold Winter Week
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In the spring and summer I wore the combination below quite a bit. That should be no surprise. By now you may be wondering if I ever washed that top. Ha! Yes, I did. It laundered beautifully and I laid it flat to dry. I think I also wore the skirt with the black polo.

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Then this fall I found this fun faux leather shirtdress from Talbots. I was impressed, but skeptical. But in the end I was delightfully surprised at how much I loved this dress. I felt like a million bucks that day when I wore it with my suede boots and red coat.

Brown Leather Dress and Knee High Boots
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One thing I am definitely learning from looking over these photos is to keep it simple. When I complicate things by over-accessorizing, over-matching or just wearing too many pieces, I’m much less happy with the end product. But I love these simpler combinations.

Faux Leather Dress & Red Wool Blend Coat
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And finally, I can’t close out this post without a nod to the two dresses I wore for Abigail and Andrew’s wedding weekend. I wore this beautiful pink eyelet dress for their rehearsal dinner, and it felt festive and feminine. I can still remember that evening like it was yesterday. Abigail’s in-laws planned such a beautiful dinner party for the attendants and their families as well as all of our out-of-town guests and family. It was a lovely night and I felt beautiful in my dress.

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And then, after ditching my first dress at the last minute (a couple of weeks before the wedding) and rushing in to Dillard’s for a “quick look,” I found the perfect dress for the ceremony. This Adrianna Papell dress was just what I’d had in mind all along.

Mother of the Bride Attire

Thanks so much for stopping in today. I’m continuing to think over these top 22 favorite outfits of 2022 to learn what I can about my ever evolving style. I think it’s so smart to take inventory like this occasionally and then apply that new knowledge to future wardrobe planning and shopping. Let me know if you’re doing something like this and what you’ve learned about your own style.

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Blessed for My Day

Occasionally I get asked about how my love of pretty clothes and coordinated outfits fits into my desire to follow Jesus. Is this a conflict of interest? I don’t think so. In fact, when the new year begins I plan to begin studying “clothing in the Bible.” You may recall as you think about it that clothing is mentioned from Genesis to Revelation, and never, to my knowledge, is it mentioned as an inherently bad thing. And I simply find it interesting that God does indeed speak of very fine clothing throughout the Bible in various settings. So we’ll look into that a bit in coming months.

But for today I do think it is noteworthy to reflect on the fact that the Proverbs 31 woman is clothed in both “fine linen and purple” and “strength and dignity.” In my estimation, that is a balance worth attaining. If we can do our part to make sure that we look lovely on the outside, but also are fortified on the inside through spiritual disciplines, I think we will be doing well. What do you think?

She makes coverings for her bed;
    she is clothed in fine linen and purple. 

She is clothed with strength and dignity;
    she can laugh at the days to come. ~ Proverbs 31:22, 25

xoxo, Kay
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5 thoughts on “My 22 Favorite Outfits of 2022

  1. Hi Kay! I read your post with great interest! It’s a wonderful conversation about clothing. Today I saw in the devotional app, Dwell, a Bible reading program titled “Dressing” which sounds like DFMD!

    I’m changing my color palette and reinventing a wardrobe post-retirement. I’m very drawn to pumps, jackets and blouses but am a stay at home gal. Hmmm! Have a wonderful safe drive home.

  2. What an enjoyable post! I hope that your drive home is very smooth. We begin our drive to the St. Louis area tomorrow, via back roads, with a stop over in Tupelo, to visit with family for about 12 days. Hopefully, we won’t encounter a lot of traffic. Happy New Year!

  3. This was a great post. Inspiring too! I also feel that tension between enjoying the creativity of clothes shopping and dressing and having a biblical perspective about it. I like your idea of tracing what the Bible has to say about clothing through Scripture. Think I will join you in that.

    Traveling mercies today! Hoping you enjoy your well-deserved break. I am one of the many who find great value in your wonderful combination of fashion education, setting an example of self-discipline, consistency, cheerfulness and kindness, and sharing your own journey, discoveries and insights with us. As a former pastor’s wife, I sense there is a deep story behind what has been going on in your church world. “Don’t grow weary of doing good.” You are already reaping a rich harvest with discretion and grace.

  4. I have occasionally wondered about that, especially early on when I first found your blog and you tube channel. However, over the course of a year I have realized that you are engaged in a helpful outreach to women. I have found a lot of useful perspective in your thoughts and advice as I’m sure others have also. Helping women can only be a good thing as far as I can see. I suppose if your love of clothing exceeded your love of Christ then THAT would be a problem! I don’t see that happening.

  5. Great stross through 2022!!! Happy to hear you had a lovely Christmas. Hope you mention the weather! I am from Western New York and we had a blizzard to rival the Blizzard of ’77!!!! I’d like to memorize scripture with you so please add me to that list when you can!!! Thank you!