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Winter Wardrobe Essentials

Building a Wardrobe
December 16, 2019

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 2019-2020 Wardrobe Essentials day!

Winter 2019 - 2020 Wardrobe Essentials

Today’s post is part of this year’s style series, Building a Wardrobe that Works for You. If you’re new to the series, you might want to catch up by at least reading the first post in this 2019 series, 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.

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.

Hint: Don’t know your personal style essence? Take my simple, quick What’s Your Style Essence? quiz.

What's Your Style_ Quiz

Finally, I’ve also discovered with my recent move to Ohio, that “winter” is quite subjective. For the first time in my life, 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

NYDJ Marilyn Straight leg Jeans // AG Angel Flared Jeans // Talbots Denim Jeggings Black

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 skinny jeans and boot cut jeans are still fashionable, but straight leg jeans have taken the lead. During the winter, however, I find myself wearing my skinny jeans or jeggings the most, since I wear them under knee high boots.

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).

Signature Slimming Luxe Stretch Straight Pant by Christopher & Banks (not in shopping widget below) // Nic + Zoe Wonderstretch Straight Leg Pants

I’ve been wearing the Nic + Zoe Wonderstretch Straight Leg Pants for two years now and absolutely love them. They’re comfortable, but also slimming and sharp. However, they’re also a bit pricey. So I’ve been doggedly searching for a comparable black pant to recommend in a lower price point. I’m pleased to say, I found them!!!

The Signature Slimming Luxe Stretch Straight Pant by Christopher & Banks is very similar to the Nic + Zoe pant at a fraction of the price. There is a difference in quality; I won’t lie. But you can definitely work with these. I’ve worn them several times now and find them to be flattering and comfortable. They’ve received mixed reviews on the website, but I think the problem is that people are trying to machine wash and dry them. I suggest washing with cold water, but then hanging them to dry. Then use a steamer or iron to get any wrinkles out. I put a tea cloth between the pants and the iron to prevent shiny marks. Also, I suggest you don’t wash these (or any) pants frequently, but only as absolutely needed.

If you’d prefer a pant with a front zip and belt loops, I recently bought these Hampshire ankle pants from Talbots and like them very much as well. I got the curvy fit.

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.

Banana Republic Ribbed Crew-Neck T-Shirt // Long Sleeve Double Trim Crewneck

I own both of the shirts above, so these are the ones I can heartily recommend. Both come in other colors, too, but I suggest at least having long sleeve tees in two shades that work well with your wardrobe. I have white, black, blue and red.

The Banana Republic tee runs true to size and has lots of stretch. I have a medium because it’s a close to the body fit. The Christopher and Banks top is generously sized and I have smalls. They also have lots of stretch, but can also “stretch out” a little with wear. Here’s a shopping widget with others that might be worth trying. I am including a v-neck in the widget, but I prefer crew necks for layering myself.

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.

Talbots Long Sleeve Turtleneck // Christopher & Banks Mock Neck

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. You might want to check out this Christopher and Banks turtleneck, too. It’s not in the widget.

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.

blue crew neck sweater (available in other colors) // camel cashmere turtleneck sweater (in other shades, too)

Some will say that these need to be crew necks, but I think you should go with whichever neckline you prefer. This year I added to my wardrobe a camel turtleneck cashmere sweater and a bright blue crew neck cotton/wool blend pullover. I can wear either alone or with a tee layered underneath. Of course, I own other sweaters. But I like adding two new solids each year.

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. Again, I prefer a cardigan in one of my chosen neutrals as well as one in a signature color.

Plaid Coatigan Sweater from Christopher & Banks // Cashmere Wrap Cardigan (similar)

The Christopher and Banks cardigan above is not in the shopping widget below, but it’s a very warm option. They have many other “coatigans” to choose from, too. But I also suggest having at least one solid option in your wardrobe. While I love my long cardigans, such as this black one, I favor the above cashmere wrap because it works well under coats.

Wardrobe Essentials Purchasing Tip – I suggest having at least one cardigan that you can wear easily under a top layer such as your coat. So consider the thickness, length and closure of the sweater.


I still think a blazer is an essential, even in the winter. Especially if you work in an environment that calls for one, of course, you’re going to want at least a classic black or navy blazer. And while plaid blazers are definitely still trending, I think a solid blazer is a best bet for that first jacket.

Red Corduroy Blazer from Loft // Black Stretch Cotton Twill Blazer from 1901

Wardrobe Essential Purchasing Tip – Purchase a blazer that fits in the shoulders. It’s difficult for shoulders to be altered, but a tailor can adjust your sleeve length. And whether or not you can actually button your blazer is up to you.

I enjoy my classic black blazer the most. It’s so very versatile. That’s why I tried quite a few before I found one that fit well and is a good quality blazer. Last night, when Talbots was having a flash sale and giving 40% off PLUS an additional $50 off of each $200 spent, I snagged this red blazer (also available in black & navy) and the matching pants. We’ll see how it turns out!

Wardrobe Essential Purchasing Tip – When purchasing a classic blazer in one of your wardrobe neutrals, I suggest spending as much money as you’re comfortable with, leaning toward higher quality. When purchasing a trendier blazer, such as plaid or corduroy, you could opt for less quality. Definitely try to purchase a blazer when it’s reduced.


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.

Brianna Tie Neck Long Sleeve Sweater Dress // from last year (similar dress)

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. And you’ll also find sneakers in animal print and embossing as well as suede.

Clockwise, starting top left: Marc Fisher LTD Dakari Faux Fur Lined Sneaker // Cariuma OCA High Suede All Camel Sneaker Women // Felicia Wedge Bootie // Steve Madden Gills Platform Slip-On Sneaker

I have the Marc Fisher sneakers above in black, but they’re available in two other shades, too. And the price is great right now. These shoes are completely lined in faux fur. Now that’s my idea of a winter sneaker! But I’ve also got my eyes on the Linea Paola Felicia wedges above. They, too, come in a number of prints and colors. I’m just waiting for the price to go down.

Wardrobe Essential Purchasing Tip – This is the time of year when I prefer to wear darker colored sneakers to match the dark colored leggings, yoga pants and jeans I’m wearing. But purchase yours in a color that works with your wardrobe.


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 waterproof and versatile.

1 State Rosita Booties


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.

See this post // See this post

My Frye leather boots were an investment purchase, but I did get them at a significantly reduced in the Nordstrom Anniversary Sale. That’s a great time to look for investment pieces like these. My suede boots are almost sold out, but I’ve got similar options in the shopping widget below.

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.


I still wear pumps occasionally, too, during the winter. I especially enjoy wearing suede pumps during the cooler months. I think having classic pumps in either nude, black or another neutral helps elevate your looks.

Ann Taylor Eryn Suede Pumps in spiced chai // Ann Taylor Yolanda Suede Bow Pumps in black

By the way, if you’re looking for a more economical option (however many of the ones above are on sale right now), I can recommend these suede pumps from Target and these.

Wardrobe Essential Purchasing Tip: Purchase pumps in a heel height that works for you. Disregard the trends and choose a shoe that is comfortable and classic, especially if you’re hoping to wear these for several seasons. And if you can’t wear pumps comfortably, skip these!

Winter Weather Boots/Shoes

For the first time ever, I’ve invested in a pair of winter weather boots. Whether you’re dealing with rain or snow, you may want some for your winter wardrobe, too.

Sperry Saltwater Waterproof Rainboots


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. 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.

This is a wardrobe essential I haven’t yet refreshed since moving here. I’m still wearing a black, faux fur collar wool blend coat that I’ve had probably 20 years. Of course, that’s the beauty of buying a classic styled winter coat. It lasts for years! Still, I’m hoping to eventually add a camel wrap coat to my wardrobe. (However, I did buy a pretty plaid wool blend coat during the NAS. It’s no longer available.)

Puffer Coat

Because I figured warmth was more crucial than fashion, I did purchase a good puffer coat for the winter. I love the warmth and the tapered waist of this Cole Haan Hooded Down & Feather Jacket. I bought it in cashew, but it comes in so many beautiful colors. And they’ve recently restocked this coat so it’s available in most sizes and colors. PLUS it’s 50% off.

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 that Mixes with Wardrobe Neutrals

tartan plaid fringed scarf (read the post)

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.

This tartan plaid fringed scarf from J.Jill has recently been marked down and is still in stock. It’s a nice thick and soft polyester and rayon blend that feels comfortable while adding pretty shades of ivory, blue and red to my black coat.

Warm Tech Friendly Gloves

Here’s another wardrobe essential I’m still working on. I have some very inexpensive gloves from Target in a full range of colors, but I’m looking for a pair of warm and more durable gloves. I definitely suggest you look for gloves that are tech friendly so you can keep them on while using your cell phone.

Versatile Hand or Shoulder Bag

While you may want to have several purses for the winter, I suggest making sure that one of them is versatile enough to use with most of your wardrobe. That way you’ll only need the one if you travel during the winter months.

Tory Burch McGraw Leather Hobo

I love my leather hobo for both casual and nicer outfits. When they were significantly reduced recently, I also purchased the same bag in moose (or brown). That’s how much I love this bag. But if you like the silhouette, but not the price, you might consider this bag.


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’ve not found the ones I really recommend personally yet. But several readers recently recommended the Simply Vera tights from Kohl’s. I’ve linked you to several options in the shopping widget. And I also hear good things from these that are available on Amazon.

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.

Winter 2019 - 2020 Wardrobe Essentials

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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

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xoxo, Kay
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11 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.