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Winter Wardrobe Essentials

Building a Wardrobe
December 18, 2023

Welcome to Dressed for My Day, where my goal, with each and every post, is to inspire and help women like you and me to dress beautifully and appropriately for our unique days so we can engage authentically and graciously with those around us and influence them well. Yes, it’s a mouthful! Hahaha! But on days like today it bears repeating. It’s Winter 2023-2024 Wardrobe Essentials day!

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In case you’re wondering what we mean by “wardrobe essentials,” you might want to check out my series, Building a Wardrobe that Works for You. Specifically I suggest you read the post 9 Keys to Building a Wardrobe that Works for You. According to that post, one of the keys is having the essentials. These essential pieces are actually the underpinnings of a functional, beautiful and versatile wardrobe. In fact, they’re the glue you need to pull outfits together. I’ve discovered that it’s important to choose essentials that are also beautiful, interesting and well made. After all, I end up wearing each of these frequently.

Red and Black Outfit for Daytime
a classic winter outfit from this previous blog post

I know that the readers here at Dressed for My Day are diverse. Some of you gals work outside the home, while others, like me, work from your homes. And many others are retired from your professions and enjoying the sweet life (you lucky dogs!). Also, while many of you are here because you gravitate toward my own rather classic style aesthetic, I do know some of you dress more natural and relaxed, feminine, rebellious, creative, dramatic or elegant. So depending on your season of life and lifestyle, coupled with your personal style essence, your winter wardrobe essentials may vary.

Late to the Trend
classic winter outfit from this previous blog post

Finally, I’ve also discovered, from living in various states, that “winter” is quite subjective. Where I live in Ohio I’m piling on the layers. Ha! Whereas when I lived in Arizona, I barely needed a jacket throughout the winter months.

So today’s Winter Wardrobe Essentials list can be interpreted loosely. You don’t need to run out and buy everything on the list. Instead, use my list to help you think about which essentials you may need to purchase or update in order to create beautiful, versatile outfits from the clothes you love to wear.

Let’s get started looking at our winter wardrobe essentials.


Great Denim

high waist relaxed jeans
 straight high waist relaxed jeans (TTS; wearing a 10 misses) from this previous blog post

I have grown to love high quality denim, but I don’t think that means you need to dole out hundreds of dollars for every pair. However, I do think, as much as most of us wear our jeans, it is important to have at least a couple of pairs that fit and flatter you beautifully.

This year straight leg, wide leg and bootcut jeans continue to be most on trend. But really, anything goes. I suggest you wear the silhouette that appeals to you most and that flatters your frame. More importantly, learn how to style the jeans you love in a way that is modern and stylish. And finally, do look for jeans in the rise (measurement from crotch to waistband) and inseam (measurement from hem to crotch) that works best for your body.

Wardrobe Essentials Photos
black straight leg jeans (TTS) (also available in curvy fit)// coat // cashmere sweater (color sold out) // boots // necklace

I also find myself wearing my black jeans more and more frequently during the winter. But the bottom line is that you need to have a couple of pairs of jeans in silhouettes and colors that work for you.

Wardrobe Essentials Purchasing Tip – Choose jeans that are trending but also functional for your lifestyle. Especially consider the shoes you’ll gravitate toward and buy your denim accordingly.

Neutral Colored Slacks

While I tend to wear jeans most days, I also like to have other pants in my wardrobe, both for dressier occasions and variety’s sake. If you’re a working gal you may want more, but even if your lifestyle is rather casual I suggest having at least one pair of other pants, preferably in one of your personal wardrobe neutral shades (see this post for determining your wardrobe colors).

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)

And while I’m all for navy, brown or even camel or grey pants, I love having black trousers in my closet. They’re just the easiest to coordinate and always look a little elevated. I enjoy recommending the black Spanx the Perfect Pant (C/O) (wearing a large) above, and I recently got the black Spanx high-rise flare Perfect Pants, too. They fit beautifully and have that modern flare.

Blouse and Pants and Jacket
blouse (TTS; wearing medium) // trousers (TTS to roomy; wearing 8) // double faced jacket (TTS; wearing large) // clutch // black pumps (use code KAYHEELS for $40 off your first pair of heels at Ally) // earrings // bracelet // gloves

If you’d prefer a pant with a front zip and belt loops, I recently bought these Tribeca ankle pants from Talbots and like them very much as well. I also like Talbots Hampshire ankle pants. But I’ve collected other great options for you in the shopping widget below, too.

Wardrobe Essentials Purchasing Tip – Purchase neutral colored slacks that you can wear with most of your signature colors. I prefer black, but you may prefer grey, brown or navy.


Long Sleeve T-Shirts

Since moving north, I’m learning to layer like never before. I often add a long sleeve t-shirt under my sweaters or sweatshirts. But these versatile tops work well under cardigans, blazers or other jackets, too. I suggest looking for tops that fit close to the body but still fit a little loose, not tight. At least that’s what I prefer for layering. If you will wear the top by itself more, I’d perhaps go with something a little fuller and loose. I’ve collected some of my favorites in the shopping widget below.

Wardrobe Essentials Purchasing Tip – Purchase t-shirts that you will be able to layer under sweaters and sweatshirts alike. You don’t have to tuck these tees in either. It’s very trendy to simply let the hem of your t-shirt peek out from under your sweater.

Basic Turtlenecks

I also like to have long sleeve, basic turtlenecks in my winter wardrobe. I have a long neck and enjoy these full coverage tops, but if they’re not your jam, just skip these. Or you could opt for mock neck tees instead.

grey perfect turtleneck // red corduroy pants (I size up to 10 in cords) //  similar coat // shoes // necklace // earrings // bracelet

Again, I suggest having these in black and white (or cream), but you might also want them in other colors that work with your wardrobe. Here are some other turtlenecks to choose from.

Wardrobe Essential Purchasing Tip – While I also love turtleneck sweaters, for layering I prefer a turtleneck that is a little thinner and that fits close to the body.

Solid Color Pullover Sweaters

As much as I love colorful striped or otherwise decorated pullover sweaters, I find my wardrobe functions best if I have at least a couple of solid colored pullovers. I suggest having at least two pullovers in colors that work well with your wardrobe, maybe one in a preferred neutral and the other in one of your signature colors.

Accessorizing Like a Master
pullover sweater // coat no longer available // jeans // Astrid organizer bag // Mediterranean long necklace (doubled over) // Interlok trio petite necklace // Intrigue Soiree two-tone hoop earrings // Intrigue bracelet

Some will say that these need to be crew necks, but I think you should go with whichever neckline you prefer.

Brighton Jewelry
pullover v-neck sweater // jeans not available // Astrid organizer bag // Interlok trio petite necklace // Intrigue Soiree two-tone hoop earrings // Intrigue bracelet

Wardrobe Essentials Purchasing Tip – This is a category for which I don’t mind investing a little more of my budget. So I choose classic cuts that I can wear for years. If I buy trendier pullovers, like oversized sweaters, I opt for cheaper versions.

Layering pieces

A Solid Cardigan

Cardigans play a larger role in my fall wardrobe, but I do suggest having at least one solid colored cardigan for winter. They’re especially nice to throw on over a shirt at home or the office. Again, I prefer a cardigan in one of my chosen neutrals as well as one in a signature color.

denim button up (similar) // cardigan // jeans // belt is old (similar) // booties // earrings

Wardrobe Essentials Purchasing Tip – For the latest info on how to look modern in a cardigan, check out this YouTube video.


I think every season calls for a versatile, flattering dress. But which dress style you select is a more personal choice. Choose a dress that works for your lifestyle, your style essence and your body shape and proportions.

Dresses from Previous Years – no longer available

While you can certainly wear other dresses in the winter time, I gravitate toward sweater dresses at this time of year. Even when I was living in Arizona, I preferred these warm knit dresses.

Wardrobe Essential Purchasing Tip – Again, consider your shoe choice as you select a dress for the winter. I think this may be the single most important fact in choosing a versatile dress for this time of year. I like sweater dresses because I can wear them with boots, booties, pumps or flats.


Let’s talk about the shoes that may be essential to your winter wardrobe, depending on your personal style essence, climate and lifestyle.


Most of us gals will want to have a pair of sneakers on hand for truly casual looks. You’ll find fashion sneakers ranging from the traditional to wedge heels to platforms. This year “field sneakers” are really trending.

48% TENCEL™ lyocell/33% cotton/19% linen
similar sneakers (more economical option)

Wardrobe Essential Purchasing Tip – You may prefer to wear darker sneakers during the winter, but it’s perfectly acceptable and on trend to continue wearing white or lighter sneakers.


Booties are probably more popular in the fall, while many of us select their grown up cousins, boots, during the winter. But I definitely still wear my booties in the colder months. And I want booties that are warm and versatile. Bonus points for being weatherproof.

black block heel booties or here or here


Whether you choose riding boots or fashion boots (or both!), I think it’s a good idea to have a pair of knee high boots in your winter wardrobe. They’re warm, functional and fashionable with jeans, leggings, cords, skirts and dresses.

quilted jacket // cashmere sweater // scarf // corduroy midi skirt (also herenecklace  // earrings // boots // earrings

Wardrobe Essentials Purchasing Tip: When you purchase your boots make sure you also buy or have on hand whatever you’ll need to protect and care for them. I suggest a waterproofing formula for your suede especially.


Wool Blend Overcoat

While I definitely need coats to help me combat wet and severely cold weather, I still think a pretty wool blend overcoat is a winter wardrobe essential. I suggest choosing a lined, warm coat in a neutral color that works well with your wardrobe.

Camel Coat and Red
single-breasted faux wool coat // black slacks // red turtleneck // black block heel booties // earrings // shoulder bag and more economical option

If you’d like a second one to add to your coat closet, select one in a pretty signature color, such as red or powder blue.

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

Puffer Coat

Cole Haan Hooded Down & Feather Jacket

You don’t have to sacrifice good style to stay warm. Puffer or down and down alternative coats are very in style, and they’ll keep you toasty warm. I love the warmth and the tapered waist of this Cole Haan Hooded Down & Feather Jacket. But I also like having a black puffer coat in my closet. I have a hooded Bernardo jacket very similar to this one.

Wardrobe Essential Purchasing Tip – I suggest looking for a coat with an added interior closure, a removable hood and a zipper and snaps.


Warm Scarf, Beanie, Tech Touch Gloves or Mittens

During the winter I definitely reach for my gloves, beanies and scarves to layer on the warmth when I step outside. I like to make sure I have these accessories in colors and even prints that coordinate nicely with each other and with my outerwear.

boots and coat
sweater (c/o; use code KayH15 for 15% off or code KayH20 for 20% off purchases of $200+) // red Hampshire ankle pants // Brighten duo tone earrings (c/o) // long station necklace (c/o) // suede booties (sold out in grey; these are similar) // coat is old // similar scarf // cardinal brooch // satchel (c/o) // similar leather gloves

While you may want to have one neutral colored scarf that works with most everything (like black or ivory), I simply suggest having a pretty scarf with colors that go nicely with your coats. That way you can add some color to your outwear where it’s most needed…around your face.

Tights & Socks

I like to wear tights with many of my dresses and skirts during the winter. But you can also wear them under pants or jeans for warmth. I suggest very opaque tights because they’re most slimming. I personally love the opaque tights from J.Jill the best.

And when I wear socks during the winter I prefer cashmere. When my socks show, I wear them to contrast with my pants and shoes. But when they don’t really show, I wear them in the same shade as my boots.

Wardrobe Essential Purchasing Tip Purchase tights in the colors of your boots, booties or other shoes you’ll be wearing. Don’t worry as much about the color of the dress or skirt. You generally want your tights to match your shoes for a longer leg silhouette.

Final Notes

Depending on where you live or your lifestyle or style essence, you may think of other pieces that are essential to your wardrobe. And of course, you’ll want to fill out your wardrobe with additional sweaters, tops, pants and skirts. But most of those pieces are style choices, not essentials. Remember, wardrobe essentials are the pieces you need in order to successfully and beautifully wear the current trends as well as the beautiful pieces you’ve collected over the years.

Thanks so much for reading today. If you’re on Pinterest, I’d love it if you’d pin the following graphic to your Pinterest board.

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Blessed for My Day

When you read God’s instructions in the Bible and you know in your spirit that He is commanding you to follow a specific course of action, how do you respond? When God spoke to Zechariah through the angel, he responded with doubt. He requested certainty. He said, “How can I know this to be true?” But basically he was demanding, “Why should I do this?” The result? His mouth was shut until God had accomplished what He had spoken through the messenger.

Mary, on the other hand, responded to the angel’s pronouncement to her with a request for clarification. She believed and trusted, but she couldn’t understand how it could be. It’s a fine line, really. But Mary proved her trust and obedience when she said, “Behold, I am the servant of the Lord; let it be to me according to your word.” The angel had given Mary much less information, but she trusted God and obeyed.

Let’s be women who trust and obey. Even when we don’t comprehend how God’s instructions will work out in our lives or situations, let’s obey and trust the results to him.

And Zechariah said to the angel, “How shall I know this? For I am an old man, and my wife is advanced in years.” ~ Luke 1:18

And Mary said to the angel, “How will this be, since I am a virgin?” ~ Luke 1:34

xoxo, Kay
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15 thoughts on “Winter Wardrobe Essentials

  1. What a perfect list of winter essentials! All the things needed for our cold midwest winters! Great tip about matching tights to the footwear. I always struggle when trying to put together a dress or skirt outfit in winter.

  2. What a wonderful and comprehensive post! It was all good information, and so well done! I enjoy everything you post, and appreciate all the hard work you put into each post. I look forward to reading you everyday! Have a merry and blessed Christmas!

  3. I recently realized I had stopped getting your emails! Our family has been in a crisis for several weeks and I didn’t realize for awhile that your emails are no longer coming in. Can you help me with this? Your posts are always so thorough and helpful. Thank you’

    1. Hi Patt. I suggest you check your spam folder and also see if you have a “promotions” folder they could be going to. Also make sure my return address is in your contacts: If you don’t get one after all that you may just need to resubscribe. I’m so sorry about this. I don’t really know what causes it.

  4. Wonderful post today Kay! ?
    Just an idea, could you put a list at the beginning or end of the items in the future, possibly so it could be reviewed more easily, maybe with small pictures.

  5. I love your blog, Kay! I have a suggestion for tights. I recently ordered MukLuks fleece-lined tights from Amazon. They are sturdy, opaque and WARM. Perfect with skirts and boots, which is my winter Sunday wardrobe!

  6. Wow! What a comprehensive list! I have to give a shout-out to Target for their long-sleeved t-shirts by A New Day. I have ordered five different colors. They are so soft and wash up really well. Today they are on sale for $8 each. Since I will be moving to a warm climate in 2020, I am now looking more towards pieces I can wear down South.

  7. Hi Kay thank you for your comprehensive and detailed list of winter essentials especially including ‘Cold Weather Essentials ‘ tops to layer , socks , tights as in the North of England UK it is Freezing 💨💦☔️❄️. I love your Pink look and Lavender and red look ‘sweaters matching coats, it looks incredible and super stylish . And the denim with the dark wine cardigan thats a winner too for me. Love the sweater dresses with opaque tights and knee high boots , definitely my style . And that chocolate cord skirt with the chocolate suede boots sooooo gorgeous . Thank you for your tip about sizing up when buying cord pants 👌🏻I love them but refrain from buying as they always seem too snug , but I will try that . I loved your BFMD about Trust and Obedience and Belief❤️Thank you for all your hard work and Inspiration and Beautiful Styling and also the Memorising Scriptures Im so pleased to be a part of this ‘Community’ but most of all Kay enjoy Christmas with your lovely family and beautiful new granddaughter . I wish you and them a Happy , Joyful and Peaceful Christmas 🎄🍾🥂Xx

    1. Hi Kym, good to be in touch here and on the Bible Meditation group. In SW London it is quite mild but really windy. I think we got a bit of Storm Pia but you had it far worse. Have a very blessed Christmas. Jan

      1. Hi Jan , pleased you are getting the weather a bit milder in London. You too have a Happy , Peaceful and Blessed Christmas and New Year with your Loved Ones Xx