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My 23 Favorite Outfits of 2023

January 4, 2024

Okay. I think this will be our final year in review post. But it’s a fun one! I’ve looked back over a gazillion photos (okay, probably more like a few hundred) and selected my 23 favorite outfits of 2023. But I didn’t allow myself to select outfits I didn’t actually wear. Many times when we take photos for a styled blog post, I do indeed wear those outfits before and/or after the shoot. But sometimes, honestly, I never do. So you’ll see a lot of mirror selfies and a few stylized outfits. But you can bet your bottom dollar that I wore them all…and enjoyed them!

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I would have been working on this post for days if I’d try to put my 23 favorite outfits of 2023 in order from 23 to 1. So instead I’m trying to group them by cool and warm weather outfits. And they’re in no particular order. I’ll share a few things I’ve learned from this little exercise as we go. Let’s get started!

Cool Weather Outfits

#1 – Cardinal Cardigan, Plaid Shirt and Relaxed Fit Jeans

I love cardinals (who doesn’t?), so I love this slightly kitschy cardinals in the snow cardigan from Talbots. While it can be a little challenging to style novelty items like this without sacrificing a sense of your personal style, I think I accomplished that here.

Talbots Black Friday
snow cardinals crewneck cardigan (TTS; wearing a misses medium) // plaid cotton button-front shirt (TTS; wearing a misses medium) // straight high waist relaxed jeans (TTS; wearing a 10 misses) // Chelsea boots (TTS) // earrings // similar red shoulder bag // As seen in this blog post.

By the way, I’m just copying and pasting the shoppable links for the items (when I have them) from the original blog posts. Some items are undoubtedly no longer available. And I don’t really have time to find substitutes if I hope to get this post published before the weekend. But we’re really talking more about composition here anyhow. All that said, you can certainly click through the links in the captions to see if items are available.

#2 – Black Wide Leg Jeans + Solid Color Pullover Sweater

I like to do this little exercise at the end of each year to help me learn which pairings really make me feel like my authentic self and help me tell the story I want to tell. The 23 outfits I’ve chose all do that. There were others I could have included in the list. For instance, I have several outfits like this simple on-trend jeans and solid color pullover sweater combo.

Jeans and Sweater Outfit
jeans // booties (use code KAYBOOTS for $50 off your first pair of boots at Ally) // cashmere crewneck sweater // necklace // earrings // bracelet

I just think everything is right here. The color flatters my face. The jeans are on trend and flattering. The pointy toe booties keep the look elevated but casual. The jewelry is simple but impactful. And it doesn’t hurt that I was having a good hair day. Ha! Oh, and that lipstick! It’s Estee Lauder’s Candy, but I don’t see it anywhere to link to.

#3 – Special Occasion but Classy and Understated

The other night I really dressed up for my anniversary dinner out. But generally when I go out for a special occasion I prefer to keep my outfit classy and a little understated. I think I achieved that with this corduroy skirt, cropped length cashmere sweater and knee high suede boots.

quilted jacket // cashmere sweater // scarf // corduroy midi skirt (also herenecklace  // earrings // boots // earrings // As seen in this original blog post.

One thing I’ve learned this year is that I generally prefer to keep the lighter color up top and the darker color on my bottom portion. Of course, that doesn’t always work, say, in the case of wearing white jeans. But since I tend to carry my weight in my hips and thighs wearing darker clothes there helps to slenderize a bit.

#4 – Striped Sweater with Black Pants & Boots

You’ll see that I’ve loved wearing stripes this year. When it comes to the classic prints – plaids, polka dots, stripes or paisley – which is your favorite to wear? I think I gravitate to plaids and stripes. But I think stripes are so on trend right now.

Late to the Trend
As seen in this original blog post. // cashmere camel and black crewneck sweater (C/O) (Use code KayH15 to get 15% off sitewide at LilySilk or use code KayH20 to get 20% off a purchase of $500+.) // black Spanx the Perfect Pant (C/O) (wearing a large) // boots (TTS) // necklace (C/O) // earrings (C/O)

But I’ve also noticed that I prefer the way the outfit comes together if I keep those stripes really minimal and simple. This cashmere camel and black crewneck sweater has turned into a real favorite for that reason.

Striped Sweater
As seen in this original blog post. // cashmere camel and black crewneck sweater (C/O) (Use code KayH15 to get 15% off sitewide at LilySilk or use code KayH20 to get 20% off a purchase of $500+.) // black Spanx the Perfect Pant (C/O) (wearing a large) // boots (TTS) // necklace (C/O) // earrings (C/O)

#5 – Red Shetland Blazer, Striped Tee and Jeans

You know I love wearing blazers. But I’ve decided that I sometimes really have to work to make the blazer I love look the way I want it to. Sometimes blazers can look a little fussy, a little overdone on me. I’m not sure I’m expressing that well, but I know what mean. I generally (there are exceptions of course) want to look classy but casual in my blazers. So I have to be mindful to create a combination that helps me come across that way.

As seen in this original blog post. // blazer // striped tee (not available in black presently) (similar) // jeans // crossbody bag // boots // earrings

I created other outfits with this red blazer that looked a little fussy to me. But I saw this style formula on Pinterest and decided to put it together from my closet. Sure enough this striped tee combined with black Chelsea boots really worked here.

#5 – Stripes & Modern Jeans & Black Quilted Coat

Since moving to Ohio, I’ve learned that outerwear is not an afterthought; it’s a integral part of your outfit. So I try to be really mindful about that when putting together outfits. I loved the way this simple black quilted coat worked with this modern sweater and jeans pairing.

As seen in this original blog post. // cashmere camel and black crewneck sweater (C/O) (Use code KayH15 to get 15% off sitewide at LilySilk or use code KayH20 to get 20% off a purchase of $500+.)  // wide leg jeans (C/O) // coat is old and no longer available // necklace (c/o) // earrings (c/o) // boots

The quilted coat is from a couple of seasons ago, so it’s no longer available. But I’m still seeing plenty like it out there. Anyhow, I just love this all neutrals combination.

#7 – Ivory, Grey and Red, Oh My!

When I realized that ivory accessories are so on trend this year and I received this ivory satchel from Aimee Kestenberg, I decided I needed a pretty ivory sweater to work with.

As seen in this original blog post. // pointelle mock neck sweater // corduroy pants // coat no longer available (similar coat) // boots // handbag // earrings

I love this combination of ivory and grey to begin with. And I think the black Chelsea boots work just fine with it. But when I added that red boiled wool coat? Oh my! The red coat is from last year, but this would work with most any similar colored coat in your closet.

#8 – Column of Denim

Every time I style a column of denim with a chambray shirt I love it. Then I completely forget to ever do it again. Ha! Seeing this sharp outfit makes me want to wear this today. We’ll see.

As seen in this original blog post. // denim button up (similar) // cardigan // jeans // belt is old (similar) // booties // earrings

I think this especially works because my jeans are relaxed fit and that “grandfather cardigan” is so on trend. Anytime we can create a column of color it’s a slenderizing effect, too.

#9 – Casual Wide Leg Trousers, Tank & Chambray Shirt

Speaking of that chambray shirt, here it is again. It’s such a great wardrobe essential. When I decided I wanted to try out the casual wide leg trousers, I began playing with ways to wear them. You know, that’s just how we have to do with new silhouettes – we have to work with them a bit. In the end I really loved this pairing with the white tank and chambray shirt. So relaxed, so modern, so fresh.

denim button-up shirt
As seen in this original blog post. // denim button-up shirt // similar tank // wide-leg casual pants (run a little large) // earrings // necklace // similar sneakers (more economical option) // belt // bucket bag

I do think some good sneakers are the key to this look, too. And the way the cognac belt and shoulder bag work together is really nice, too. (I gave that bag to my daughter for Christmas. Yes, my bag. She better enjoy it…cause I’m already missing it!)

#10 – Casual Wide Leg Trousers, Striped Tee, Loafers and Sweater

I limited myself to two outfits with these wide leg trousers in my list of 23 favorite outfits of 2023, but I could have shared more. And I did indeed wear these outfits and others with the trousers in the fall. I haven’t worn them in the winter yet, but I will in the spring. I loved this black, white and khaki trio.

As seen in this original blog post. // long sleeve tee // black cashmere v-neck sweater // Harlow wide-leg pants //  belt // loafers (more economical option) // bag // necklace //  earrings 

I’ve really enjoyed creating outfits with matching accessories this year. That’s very on trend right now. While it’s certainly not necessary, it does create a little extra polish when you {somewhat} match your shoes, handbag and belt. And I think it’s smart to build your accessories wardrobe accordingly.

#11 – Oatmeal Cotton Sweater with Black & White

I love, love, love my oatmeal colored cotton fisherman sweater from Jenni Kayne. It’s one of my favorite things about spring! And I’ve discovered that my favorite way to wear it is to just keep things very simple.

What I Wore Friday
As seen in this original blog post.

So the sweater with black jeans and ballet flats was very on trend for 2023. We’ll see if they’re still on trend this year. And I loved how that black and white mac from Talbots worked here. Just so classy but also casual and comfortable. I love spring. Ahhh.

Warm Weather Outfits

#12 – Veronica Beard “Suit”

Man, I love my Veronica Beard Miller dickey jacket, too. In fact, yes, I’m getting the black one today. I just couldn’t resist any longer. I wear this navy blazer so much, so I think the investment is good. But I have to tell you, I tried on the similar double breasted blazer in Talbots’ new collection and the fit is spot on. I did size down in an 8, and I didn’t buy it. But I can highly recommend it. No, the quality is definitely not the same. But it’s good. And it drapes really nicely. Okay, let’s leave that rabbit alone and move on with this smart Veronica Beard “suit.”

What to Wear to a Memoria Service or Funeral
As seen in this original blog post. // similar blouse // navy blazer (more economical option) // coordinating navy pants (more economical option) // block heel pumps (use code KAYHEELS for $40 off your first pair of Ally heels) (more economical option and lower heel option) // shoulder bag (different color) // necklace // similar earrings

I put “suit” in quotation marks because these are actually just separates that do coordinate. And I love the look. I think the ankle length keeps it really modern and fresh. I wore this combination several times this year.

#13 – Black Cropped Pants, White Tee, Splash of Color

I LOVED wearing these black cropped pants this summer and into the fall. And they’re still available and in a wide selection of colors, too. They have such nice stretch in them and a high waistband. Looking back over photos of me wearing them, I found a couple that suited me best. I especially liked the black pants with a simple white tee and a splash of color from this cashmere vest.

As seen in this original blog post. // white tee // pink vest // black pants // belt //  mules (also in cognac) (more economical option) // necklace // earrings

One of the most profound lessons I learned from this exercise of reviewing my outfits of the year is that I feel and look most like me when I wear mostly neutrals with, perhaps, just a splash of color. If you look through these photos you’ll see that over and over.

#14 – ✨ Column of White with Linen Chambray Shirt

I don’t know if this outfit is my ✨ absolute favorite of the year or if it’s just that this photo is my favorite of the year, but I love this look. It’s clean, crisp, airy and fresh. It’s also minimalist but impactful and on trend.

3 Ways to Wear Linen Relaxed Crops
As seen in this original blog post. // linen relaxed crops // tank // similar button-up shirt // sandals // necklace // bracelet // earrings // watch (Use code KAYHRMS for 15% off your purchase) // similar handbag

That outfit photo makes me long for warmer weather. What about you? I also have noticed that I feel more confident putting together good outfits in the warmer months. Is that easier or harder for you? Anyhow this outfit reminds me how much I love a good column of white. Such a great style for spring and summer, whether you work it with linen or denim or cotton.

#15 – Travel Outfit

I wore some variation on this travel outfit so many times this year. And I always felt like myself and a little stylish, but also comfortable and ready for whatever the day of travel may bring.

Travel Outfit
As seen in this original blog post. // Talbots’ travel pants // striped shirt (similar short sleeve top) // sandals // trench coat // scarf // Away bag // necklace // earrings // watch (use code KAYHRMS for 15% off)

Looking back over my photos, I found so many other outfits very similar to this one. In fact, I did wear that striped shirt a lot, as well as my travel pants.

#16 – Keeping it Fun!

As much as I love a somewhat sophisticated, minimalist look, I really do enjoy creating more joyful, fun outfits some, too. And I found several amongst my photos that qualify as favorites. But I decided that this accordion skirt, white tee, cashmere vest and t-strap Mary Janes combo best represents that side of my personal style.

Pleated Midi Skirt Styled for Fun
From this original blog post.

Those t-strap Mary Janes were definitely controversial in the comment section of that blog post. And I get it. Those are shoes you’re either going to love or hate. But that’s sort of the essence of fashion: it’s personal. And indeed I found them to be fun to wear. If I feel like they’re still on style this spring, I’ll definitely wear them some more. And yes, I absolutely did wear this outfit out and about, as demonstrated below.

As seen in this original blog post. //  pleated midi skirt // crewneck tee // cashmere vest.//  croc-embossed cutout loafers // bracelet // earrings (similar) // shoulder bag 

I remember I wore that outfit to the mall one day. I got SO MANY compliments. You can certainly play it safe, and I do quite often. But I’ve discovered that good style sometimes requires that we have a little courage and be willing to take risks. I truly enjoyed wearing this fun outfit and would wear it again in a heartbeat.

#17 – The Skirt of the Summer

This colorful floral skirt was a little pricey, but it turned out to be the skirt of the summer. I must have worn this exact outfit (with maybe a tweak or two) a dozen times. When I found that purple sweater tank at J.Crew I knew it was the perfect topper for this unique skirt.

As seen in this original blog post. //  Denim Jacket //  Bracelet

This outfit is a reminder to me that sometimes it’s smart to buy the “pretty thing that catches your eye.” While I’m a huge proponent of stocking our closets with the essentials in versatile solids, we do need a few “show stoppers” to keep things interesting, too. But keep in mind that it’s the essentials like the denim jacket and gold sandals that pull this outfit together so nicely and make it feel like me.

#18 – White and Beige Linen

I have tons of photos of linen outfits because that’s basically all I wear in the summer. And truly I love many of those outfits, too. But this one epitomizes my perfect summer outfit because it’s relaxed and casual but still polished and soft.

The No-Fail Style Formula to Looking Cool & Classy in the Heat
As seen in this original blog post.

I wore all of those separates so much this summer. But I especially like how they play together with that effortlessly chic look.

#19 – A Graphic Tee with Cropped Black Pants

This outfit was created with those same cropped black pants I shared above. Here I wore them with a whimsical graphic tee and coordinating accessories. Yes, there are those matching accessories again.

Look Polished in Casual OUtfits
As seen in this original blog post. // cropped wide-leg pants // graphic tee // belt // shoulder bag

I remember I wore the outfit above to church that morning (we have a very casual house church). But for the blog post I also wore the outfit below. And later when the weather got a little cooler I did wear that variation out and about as well. I love them both.

Wear a Little Black
As seen in this original blog post.

#20 – Mixing Stripes and Plaid

I mentioned earlier that my favorite classic prints are plaids and stripes. Well, I think it’s fun to mix those, too. The outfit below is one where I did that and I think it worked beautifully.

Loose Fitting Blazer with Wide Leg Jeans
As seen in this original blog post. // wide leg, full length jeans // effortless jersey stripe square neck top (size down; wearing a Small) // houndstooth blazer (size down; wearing an 8) // necklace // belt (wearing m-l) // convertible shoulder bag // similar sneakers (GREAT more economical option)

Of course, I do believe that Talbots actually even showed that blazer and striped top together, so it’s not like I invented the wheel here or anything. Ha! But I loved the way this worked with these modern wide-leg jeans and sneakers.

Close Fitting Top with Wide Leg Full Length Jeans
As seen in this original blog post. // wide leg, full length jeans // effortless jersey stripe square neck top (size down; wearing a Small) // houndstooth blazer (size down; wearing an 8) // necklace // belt (wearing m-l) // convertible shoulder bag // similar sneakers (GREAT more economical option)

#21 – Another Whimsical Look

I mentioned dressing with joy and whimsy above. It’s just something I like to do some days! And here’s another fun outfit that falls into that category beautifully. I wore this trio when I helped style outfits for women at J.Crew one Saturday.

As seen in this original blog post. //  cashmere cropped cable-knit sweater-vest // chambray trousers // belt 

Those chambray trouser are really comfortable, so this outfit looks pulled together, but it feels great. I think for many of us that’s the ideal we’d like to achieve most days.

#22 – The Trending Denim Skirt and Vest

This outfit combines several 2023 trends that I was all in for. I’m wearing the modern midi length denim skirt, a classic white tee, the trending vest, hoop earrings and a thin leather belt. And I loved how this came together.

As seen in this original blog post.

I anticipate that these denim skirts will still be on trend this spring, but we’ll have to wait and see I suppose. I know one thing; they flew off the racks this summer and fall.

#23 – My Feminine, Flirty Skirt

I definitely think I wore and enjoyed skirts more this year than in recent years. Maybe that’s because the midi length has been so on trend, and it’s the easiest for me to wear and feel comfortable in. I have LOVED having this silky, gauzy Vince skirt in my closet. I got it in the Nordstrom Anniversary Sale, and it was undoubtedly my best purchase of the sale. This new arrival in azurite blue is similar, but it doesn’t have the smocked waistband.

7 Keys to Getting Out the Door Looking Fabulous
As seen in this original blog post.

I have worn this combination several times, but the photo above was taken when I spoke at a ladies’ night out event. It felt perfect for the occasion.

I enjoyed looking through my photos for my 23 favorite outfits of 2023, and I enjoyed walking you through them and jotting down notes. This has really helped me have some clarity about putting together outfits that reflect my personal style aesthetic and tell the story I want to tell. I hope you’ve enjoyed tagging along. Have a great day!

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Blessed for My Day

Do you ever have thoughts of doubt or discouragement come into your mind from seemingly nowhere? I do. Sometimes I even wake up with a shroud of doubt and discouragement clinging to me tighter than my bed sheets. I’ve learned that those thoughts and feelings present me with an option. I can fall into them or break away from them. Inaction is not an option. One way or the other I’ve got to deal with them. 

Some days, I confess, I wrap those feelings of doubt and discouragement around me all the tighter as I begin to ruminate on the memories, unfulfilled desires or dissatisfactions that blanketed them on me to begin with. But most days I recognize the initiator of those feelings and thoughts for who he is, the deceiver, Satan. And I have learned to confess those thoughts and feelings to God so that He can help me shake them. Then I find a truth in God’s Word to write down and cling to for the rest of the day, returning to it over and over until I’ve broken free completely.

And the tempter came and said to Him, “If You are the Son of God, command that these stones become bread.” But He answered and said, “It is written: ‘Man shall not live on bread alone, but on every word that comes out of the mouth of God.’” ~ Matthew 4:3-4

xoxo, Kay
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16 thoughts on “My 23 Favorite Outfits of 2023

  1. I truly love all of your 2023 outfits, except for being as short as I am, 4’11”. I just have a problem as to what length or inseam to wear. I really cannot like the flare or boot cut jeans. I did when I was younger. I’m 74 now. I think between the ages of 30 and 50, I don’t remember what I wore. Have you ever been thru that? The jeans lengths are what I struggle with. I’m usually a jeans
    girl, but I do have other pants I wear in the different seasons. Same problem. Thank you for this wonderful blog. I hope your daughter, son in law, and grand baby are doing. Wishing you the best 2024! –Linda

  2. What a fun look back at your favorite outfits of 2023! I’m inspired to begin taking some outfit pictures in 2024 (probably not every day!) to see any pattern to what my favorites are. Also might be helpful to take pictures of outfits that just don’t look quite right. I love my spring and summer outfits, but struggle to put together fall and winter outfits that I like. Your blog is a huge help. Looking forward to your daily outfits on Instagram.

    Thank you for today’s BFMD and the practical advice on how to break free from the lies Satan wants us to believe.

  3. Kay, there was an ad after every picture today. I made it cumbersome to read, maybe this is a glitch you can let your tech people know about. I was reading on a laptop if that makes any difference.

  4. Kay, I agree with your choice of best outfit/picture for 2023. Easy, breezy white linen. You look so tan in that picture it makes me wish for an early spring. Thank you for all your effort in making this blog #1 on my list. Blessings for a wonderful year ahead.

  5. Thank you, Kay, for all the wisdom you impart. I have purchased numerous items that you have modeled and have learned a LOT about how to dress for my style. Like Linda, I’m short so I can’t do wide leg pants very well. I have discovered that my perfect inseam length is 25″–I’m 5’2″. I’m also quite curvy, so your idea about “light on top” rarely works for me! Black on top works best because I’m full-busted, although a crisp white blouse that doesn’t hug my body works.. I’ve tried ordering from the same vendor when the first pair of pants I ordered were perfect (LOFT). The next pair (high-waisted jeans) wre pretty good. The black “skinny” pants I couldn’t get buttoned, so they will go back. What I’ve enjoyed the most from your suggestions during the past year is my dark wash denim jacket, my white denim jacket, and a navy-white striped summer dress. I wish I knew how to take “selfies” showing my entire outfit. So far I’ve had no luck). Your idea about dressing “modern” but not “younger” is so appropriate. At 78 years (everyone tells me I don’t look it) I do not wear sleeveless tops or dresses, nor do I wear plunging necklines. Your blog helps me be current! Thank you so much.

  6. Really found BFMD to be so apropos; thank you. Fun to look back on 2023. Some of your faves were mine as well.
    I do wonder if you will begin wearing more silver jewelry since your hair color is now gray. You seem to wear cooler colors rather than warmer colors. Cool colors are lovely with silver. Just curious.

    The best to you and your family in 2024!

    1. Hi Barb, I used to wear only silver all the time. So I got kind of tired of it. I’ve really enjoyed wearing more gold in recent years. I think what really works best for me, however, are mixed metal pieces. That way I can wear my silver and gold. Good question!

  7. I love all the wide leg jeans and pants. Very nice outfits on you. I like strips and plaid best too. I find it more fun to dress in fall and winter because I can wear more clothes like jackets blazers and coats. I can wear tights to cover my legs and wear shorter skirts. I can wear boots. In Texas summer is so long and hot, I get in a rut with shorts and T-shirts. In the summer I do enjoy wearing sandals and linen. This year I am going to try to buy natural fiber clothing and go for quality and classic. I’m finding it’s very wasteful to buy clothes and shoes just for a season to stay “on trend”.

  8. Loved those looks and remembered most of them-and got the jeans I admired for a great sale price by now! Thank you!

  9. Do you have some favorite verses that you cling to when you are discouraged? I really need to get my eyes off me and on Him and who He is. I am just becoming aware that it is a fight, For years I have simply let my mind think about whatever it wanted to think about, not realizing i am having a pity party with satan. I look forward to getting better at this and becoming a positive person.

  10. Love all the outfits!! One that I really loved was the one with the Snoopy tee. It was such a great casual outfit and looked great on you!!

    1. Yeah, that one was indeed a contender, but I had to draw the line at 23. I feel like I had more outfits I liked this year than in past years, so that’s progress!

  11. Thank you for your blog, which I just discovered a couple of weeks ago. I enjoy the “blessed” thought at the end and I was really touched at your introduction abut why you started the blog to take your own life changes and help others see that we have a purpose and can feel proud each day and contribute with grace and a smile.

    I love how you take photos of yourself almost each day. It is helpful to see how various styles look on someone my age, a real person.
    And it helps me consider new things to try when it might otherwise be too much time and money for me to find and try all options. Helps me consider branching out.

    I have been going through an extreme life change over the past 5 years due to other people’s choices, that has been devastating, and one big casualty has been my sense of being attractive or able to even have funds to purchase basics. Your photos have given me inspiration to look through my closet for a little flair again, and for things I can make more current and stylish with some very small changes—as well as ideas for how a few simple inexpensive purchases like an on trend fabric can help me look and feel special again

    Thank you.

    1. Hello and thank you so much for sharing. I’m really glad my content has been helpful to you. I think you’ll love the new style series I kicked off today. Make sure you’re subscribed to my email so you’ll get notified each time I publish new content. Bless you. You are on the right track! Hang in there.