It's so nice to meet you!
Get to know Kay...

Trending Classics for Winter 2023-2024

December 12, 2023

While I like to keep my style fresh and up-to-date by participating in some trends each season, I always prefer to jump on board when the trend is in fact a classic that is, as we say, “having a moment.” This year classics as a whole have been trending, and I see that momentum continuing into the new year. If you, like me, have a fairly classic wardrobe, now is the time to pull a few key items to the front of your closet. That’s why I’m sharing a few trending classics for winter 2023 – 2024 today.

Trending Classics winter 2023 2024

This post contains affiliate links. When you shop through my links I potentially earn a commission on your purchases, but at no additional cost to you. Thank you so much for supporting my work here by shopping my links.

In fact, if you find this helpful, I may make this a quarterly post. I know that many of my readers share my personal style aesthetic of “modern classic,” so keeping abreast of the classics that are most “in style” at the time may be beneficial to us all. Let me know if you like the idea of this quarterly round-up and I’ll schedule it again for early spring.

Here are the trending classics that I’m seeing everywhere this winter. Some are specific items, while others are ways of wearing things. You’ll see as we get going.

Black Trousers

I won’t state the obvious every time, but of course black trousers are indeed classic wardrobe basics. We probably all have a pair or more in our closets. And I’m seeing quite the emphasis on them this year. I chalk that up to the trend we’re seeing in elevated basics. Wearing a pair of sharp black trousers is such a great way to elevate any outfit.

Late to the Trend
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) as seen in this BLOG POST.

I have several pairs of great black trousers, and I’ve ordered two more recently. Above I’m wearing the Spanx Perfect pants in slim straight. These are my go-to black pants when I want a really trim look. They work just like your Spanx undergarments, but are extremely comfortable. I am wearing a size large. And just yesterday I received the Spanx Perfect Pants in the high-rise flare cut in the mail. I immediately tried them on and they fit wonderfully. They’re definitely long (I got the regular and they come in tall and petites, too), so I’ll be wearing them only with heels.

Black Pants
Spanx Perfect pants in slim straight

I also ordered the Veronica Beard Hibiscus scuba pants, which feature a flare leg, too. They’re quite pricey, but I’ve heard such good things. And I wear black pants year round so much. They really are my favorite, and I’m so glad they are trending this year. But meanwhile I also enjoy my Talbots Tribeca ankle pants and my Talbots Hampshire Ankle pants, which sit a little lower on the waist.

Blouse and Pants and Jacket
 black Tribeca pants

I’ve filled a shopping widget with additional great black trousers. And while you certainly can swap in classic navy or gray trousers, I find that black are the most on trend right now.

Full Skirts

While I’m still seeing the slip skirt quite a bit, I’m noticing even more full skirts. And I understand from my research that we can expect to see fuller skirts in the spring and summer, too.

skirt // cardigan

Of course, I think it’s delightful that skirts in general are trending. I’ve really enjoyed the accordion pleated skirts in recent years, and they’re still looking very contemporary but oh so classic.

Styling a Pleated Midi Skirt 2 Ways for Fall
pleated midi skirt // shrunken sweater // suede block heel pumps, (Use code SARAHFLINT_CCLAURAKAY1 for 15% off at Sarah Flint, new customers only) // necklace // earrings (similar) // bracelet // similar clutch

Button-Up Shirts

Yes, button-up or button-front shirts continue to trend into 2024. And if you love a crisp, slightly oversized button-up shirt I’m sure you’re all in. But I know women either love them or hate them.

Belfast triple-fleece English peacoat
Joedy button-up shirt // Belfast triple-fleece English peacoat // East Galway denim jeans

After discovering the Joedy button-up shirt from Frank & Eileen I’ve come to love my button-up shirts. I do think that quality makes a difference in this classic piece, just as it does in most. I never cared for button-up shirts before because they always seemed so uncomfortable. But this lightweight, crisp and fuller shirt feels so nice on. Since finding it I’ve found others I like equally, such as this Citizens of Humanity Kayla shirt.

Fair Isle Sweaters

I don’t actually have a new Fair Isle sweater to share with you, but I’ve enjoyed them in the past. This year I’m seeing even more of them available and in a wider variety of styles.

What I Wore for an Autumn Day Trip
from last year // outfit items no longer available

You’ll definitely see Fair Isle sweaters that look very holiday-ish, but I also see a many (like mine above from last year) that look appropriate all winter long. I found so many beautiful Fair Isle sweaters for you to check out in the shopping widget below. I think my favorite is this icy blue.

Socks and Tights

Don’t you just love it when you hear that something as classic as socks and tights are trending? Yay for keeping warm! In fact, I think that’s the bigger picture here. Remember, wearability is one of our trending themes this year. It’s all about being able to wear your garments with confidence, comfort and ease.

Red and Black Outfit for Daytime
red Hampshire ankle pants // black cashmere turtleneck // similar loafers (more economical option) // socks // necklace // earrings bracelet 

I’m all for keeping my feet toasty warm, so I’ll definitely be wearing socks this winter. And this year the trend is to wear fun, colorful or contrasting socks that show. If you want to be truly fashion forward, try wearing longer socks with your sneakers and pulled up over your leggings or joggers. Hmm. Not sure I’ll do that, but I never say never.

loafers // socks // jacket // turtleneck

And yes, you’ll look contemporary in your classic tights this year, too. Wear them confidently with skirts, sweaters dresses, jumpers and more. We’re even seeing those with patterns this year, too.

Shades of Red

I think the color red qualifies as a classic, don’t you? Well, it’s definitely classic in my closet. And this year I’m enjoying wearing all my red! Shades of red from burgundy to salmon to saffron to beet, they’re all trending right on through into 2024.

Blouse and Pants and Jacket

And while red garments, shoes and other accessories are definitely on trend, it’s also very on trend right now to wear a bold red lip. I read somewhere just yesterday that every woman should spend a little time at the makeup counter scouting out the perfect shade of red for her. Yes, we absolutely ALL can wear red; we just need to find the shade(s) that works best for us.

Red Coat and Red Turtleneck
double-breasted wool-blend coat // black slacks // red turtleneck // black block heel booties // earrings // leather shoulder bag and more economical option

By the way, when I wear something red, especially close to my face, and I don’t have a lipstick that perfectly matches, I wear a nude lipstick. That works perfectly every time. Recently I picked up this Yves Saint Laurent lipstick in nude lavalliere 44 and it works perfectly with anything that I don’t have the right match for. Plus, it’s just a great lipstick.

Clutch Bags

Now here’s a classic that many of us may actually be short on: clutch bags. And these chic handbags are definitely trending right now. True, they’re not the most practical bag, but I think it’s fun to choose to carry one at least for special occasions.

Blouse and Pants and Jacket

And I am finding more and more clutches that are a little roomier and thus a little more practical. I can easily fit my reading glasses, keys, card pouch and lipstick in this supple Allsaints leather clutch above. Those grommets make it look so modern, but it’s still classic enough that I feel confident in investing in it. The bag is also available in grey.


I shared all about this trending classic in this previous blog post. Of course, we’ve seen lots of stripes in button-up shirts this year, too. But the biggest place I’m seeing trending stripes for winter is on sweaters. And I’m all in!

Striped Sweater
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)

Shiny Silver

Obviously silver is a classic, but this winter we’re seeing silver shine like never before. And by shine, I mean shiny! The holidays are perfect for adding shiny silver accessories and garments to your look. But I expect this lustrous trend to continue past January 1st and into 2024.

Winter Style Trend: Joy
sweater (c/o; use code KayH15 for 15% off or code KayH20 for 20% off purchases of $200+) // red pants (also in other colors) // silver loafers // crystal ball earrings

I’ve only, and quite literally, dipped my toe into this shiny silver trend with my silver loafers, shown above. But I’m considering buying other silver pieces, such as these sequined pants (maybe for my 60th birthday coming up in February?!). I think this silver trend could be a fun one to participate in. What do you think?

Monochrome Dressing

Like all of our trending classics, monochromatic dressing is nothing new. And in fact it’s been trending for several years now. A monochromatic look is always easy on the eyes, even if the color of choice is bold and big.

Party Outfits
cashmere charming cardigan // red Hampshire ankle pants // suede Evelyn pearl pumps // necklace // earrings // bracelet

Above I’ve actually worn the same red head to toe, just in different textures. But you can create a monochromatic look with various shades of the same color, too. It’s such a modern style choice, but really quite classic.

So which of these trending classics will you be pulling to the front of your closet this winter? And will you be adding any of them to your wardrobe? Honestly, these are the kinds of trends I don’t mind investing a little in because, while they are “having a moment,” they are, indeed, timeless.

Don’t Miss a Post:

If you like what you’re seeing here at Dressed for My Day, I invite you to subscribe to my email list. You can receive an email each time I post (about 6 times weekly) or just on Saturdays. You choose! But you’ll also receive the password to open up all the subscriber freebies I offer.

Would you like to subscribe to Dressed for My Day?

Spread the love

Blessed for My Day

The prophesies about the Messiah may have seemed vague, mysterious or even unsettling to the Israelites. But the promise of a child who would be born of a virgin and then named “Immanuel” must have been astonishing to them. It certainly amazes me every time I read that name in Scripture. Emmanuel (in the New Testament Greek) – God with us. A people who walked in darkness, struggling to keep the Law and failing over and over, dispersed and oppressed and demoralized…surely they chilled at the thought of God dwelling amongst them.

As Christmas approaches let’s whisper that name to ourselves over and over. Let’s try to wrap our brains around the fact that God came down to dwell among sinful man so that He could restore our relationship with Him. Ahh, what love! What compassion and mercy and grace. And while Jesus, Emmanuel, died and rose again and ascended into heaven, He later sent His Holy Spirit to dwell, not among us, but in us. Emmanuel. God with us. God with me. Praise Him!

Therefore the Lord himself will give you a sign. Behold, the virgin shall conceive and bear a son, and shall call his name Immanuel. ~ Isaiah 7:14

xoxo, Kay
Join the Conversation

This site uses Akismet to reduce spam. Learn how your comment data is processed.

13 thoughts on “Trending Classics for Winter 2023-2024

    1. Kay usually has more inexpensive options in the shopping pictures. Also, you can look at past posts that she has done from Kohl’s and I think she did one on Walmart. It is easy to look at the outfit and find cheaper versions of it at more economical prices.
      Merry Christmas!

    2. I tried to include a variety in the shopping widgets at a full range of prices. But I also only recommend items that I’m pretty familiar with. That said, yes, when I work on one of these for spring I’ll definitely make an effort to include a full range of prices. I threw this together yesterday afternoon and did the best I could in limited time. Thanks so much for reading!

  1. I would love to have you do posts on updates of trending classics. That would help me keep in the loop in a fun and enjoyable way. Always love your posts.

  2. Loved this post. My style is classic/preppy since high school in the early 80’s and one of my favorite colors is red. I’m a Georgia Girl and my 60th birthday is in February, as well.

  3. Kay, I always enjoy your posts and would love for you to give us a quarterly update on trends. I am actually wearing one today, red sweater with red jacket. Not sure I would have thought of wearing these together but you inspired me. Appreciate you!

  4. Hi Kay I Loved your post about ‘Classics’ and yes I think it would be fabulous having a ‘Quarterly Classics Trending’ Blog Thank you . Loved ALL your outfits but loving particularly the Striped Sweaters , Fairisle Sweaters (specially that baby blue one) , the pleated skirt and that Red Monochrome Outfit ….Totally Gorgeous. Thank you for all your hard work and Styling Inspiration ❤️. Not long now for the wait for that little bundle of Joy to be with you all. P.s So pleased your Orthotics are helping you Xx

  5. I have everything you mentioned in my closet but an accordion pleated skirt. Black pants are a weakness of mine. Socks and tights are always something I wear in winter. Today I wore Christmas socks that didn’t match the color of my my shoes. I like the look. I like the Spanx pants and the red coat and jacket. I would like a quarterly update too.

  6. Thank you, thank you, Kay for including a Classics theme! I don’t like jeans, never have so it’s so good to see a variety of trousers. Love your site.

  7. Kay, I also love the classic look and really appreciated this round up of classic items that are on trend. Please update this type of post seasonally for us.

    Thank you for all you do!

  8. I will be wearing socks and red. And even red socks. 🙂
    Thanks for this post. I am definitely interested in seeing posts regarding classics pieces that are trending each season.