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

Winter Wardrobe Essentials 2020-2021

Building a Wardrobe
December 16, 2020

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 Wardrobe Essentials day!

One of the 9 Keys to Building a Wardrobe that Works for You 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. And I’m also keeping some of these in my wardrobe for years, even decades.

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.

Finally, I’ve also discovered with my 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.

Winter Wardrobe Essentials Video

I’ve also uploaded a video about Winter Wardrobe Essentials. You can watch it now or later. And be sure to subscribe to my channel on YouTube. If for some reason the video player does not load below, you can watch the video here.

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


Great Denim

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.

J.Crew Straight Jeans
cotton sweater (wearing a small) // jeans (wearing 29) // belt (wearing medium) // boots (sized up .5) // necklace // earrings // bracelet (sold out – comparable substitute) // safari jacket // hobo bag (faux leather option)

This year skinny jeans and boot cut jeans are still fashionable, but straight leg jeans have taken the lead. I like the J.Crew 9″ vintage straight jeans in vintage medium wash above. They’re a great basic straight leg jean with a pleasantly relaxed fit that isn’t ultra baggy. I’m also enjoying my AG Mari high waist ankle slim straight leg jeans shown below. They’re pricey, so watch for a sale.

Column of Denim with a Pop of Pink
AG Mari high waist ankle slim straight leg jeans // denim shirt // similar boots // necklace // earrings // coat (similar coat more in stock) // bow pin

During the winter, however, I find myself wearing my skinny jeans the most, since I wear them under knee high boots. And honestly, straight leg jeans can be a little trickier to pair with the right shoes or boots.

Soft and Subtle
cashmere sweater ($75 Wednesday special) // Levi’s 721 High Rise Skinny Jeans // 40-Hour Flats in taupe // pearl necklace old (similar) // pearl earrings old (similar) // Day Market Tote

Above I’m wearing the Levi’s 721 High Rise Skinny jean, and it’s available in a number of other washes. But I’m also a big fan of Talbots’ denim jeggings. Don’t let the name fool you; they feel and fit like jeans, not leggings.

Color Me Beautiful!
Talbots’ denim jeggings (these are the dark wash jeans in the video) // relaxed balloon sleeve sweater // suede buckle mules

I also find myself wearing my black jeans more and more frequently during the winter. Below I’m wearing my current favorites, the wash black super-straight jean from Everlane (the blue denim selection did not fit me the same at all).

Black Straight Jeans
cotton boat neck sweater // washed black super straight jeans // reversible plaid ruana // loafers // reversible belt // gold teardrop earrings //  multi strand bracelet

Of course, you also may be one of my readers who prefer flare leg or boot cut jeans. I love the flare leg and boot cut jeans at White House Black Market. They’re long enough for my 5’8″ frame, but come in several different lengths and size ranges. But the bottom line is that you need to have a couple of pairs of jeans in silhouettes and colors that work for you.

Flare Leg Jeans & Turtleneck Sweater

TIP: I have more jean options in my recent Winter Denim Lookbook.

I’ve prepared shopping widgets for each category of wardrobe essentials. The links in the widgets and in the copy of this blog post are all affiliate links. If you shop through them I potentially earn a commission, but at no cost to you. Thank you for shopping through my links and helping me to be compensated for the work I’ve done to help you prepare your wardrobe for the winter.

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 Color 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 three 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.



I didn’t mention camisoles in the video, but I did show myself wearing one under the layering tee. During the winter I frequently wear a stretch camisole that fits close to the body but not tight. You absolutely can find camisoles that are slimming, but I’m looking for something more comfortable than that. I really just wear these for warmth.

Wardrobe Essentials Purchasing Tip – I prefer to have a couple of colors of close fitting camisoles so that I’ll have what I need for all the sweaters in my wardrobe. I have black and flesh toned camis.

Long Sleeve Layering 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 some of these versatile tops work well under cardigans, blazers or other jackets, too. The ribbed crewneck layering tees from Banana Republic shown below can definitely be worn alone or under a jacket or cardigan.

Layering Tees from banana Republic
Ribbed Crewneck Layering Tees from Banana Republic

You can see how I styled these tees in the following photos.

5 Ways to Wear a Red Suit
Ribbed Crewneck Layering Tee // See the original post.
Favorite Travel Outfit Two Ways
Ribbed Crewneck Layering Tee // See the original post.

The t-shirts above are the ones I prefer if I’m wearing them under something that is open. But I love the thinner layering tees from Nordstrom for wearing under pullover sweaters because they don’t have the thick seams around the collar or sleeve cuffs, and they lay smooth on my skin.

Layering Tees from Nordstrom as shown in this video

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.

Layering 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.

Tartan Plaid Holiday Look for Women Over 50
Ribbed Turtleneck from Talbots // See the original post for details.

I enjoy wearing turtlenecks like these alone (often with a camisole under them) or under a sweatshirt or sweater.

Nordic Inspired sweater
long sleeve turtleneck from Talbots // See the original post for details.

I can personally recommend these three turtlenecks because these are the ones I own and wear. I like the thinner long sleeve turtleneck on the left best for layering and the ribbed turtleneck on the right for wearing alone or under puffer vest. The middle turtleneck is from Christopher and Banks and it is a well constructed budget friendly option.

And hey, if a striped or leopard print turtleneck is more your style aesthetic, go for it! You can absolutely treat either of those the same you would a solid.

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.

Pullover Sweaters in Your Neutrals and Signature Colors

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.

Sweater Weather
cable-knit cropped sweater in whipped cream (also available in beige taupe and rich red wine) // See original post for details.

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 cable-knit cropped sweater in whipped cream and a cashmere Audrey sweater in light rosewood heather. I can wear either alone or with a tee or camisole layered underneath. Of course, I own other sweaters. But I like adding two new solids each year.

Classic and Smart
cashmere Audrey sweater in light rosewood heather (just $75 Wednesday only) // See original post for details.

I also recently added the red cableknit sweater you saw me wore in the accompanying video and the black and ivory Fair Isle sweater I recently shared in this post.

red cableknit sweater // black and ivory Fair Isle sweater I recently shared in this post

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.


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.

The two dresses I showed in the video are from years past and are no longer available. But I have lots of selections in the shopping widget below.

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.

What I Wore on Our Weekend Outing
Linea Paolo wedge sneakers // See the original post for details.

I’ve been wearing my Linea Paolo wedge sneakers for about a year now and still absolutely love them. I like the way the elevate a look but keep me feeling comfortable and casual.

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.

Waterproof Booties


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.

Tips for Staying Fit Through the Holidays
Blondo Rachelle Waterproof Boots // See the post for more details.

In today’s video I suggested these Blondo Rachelle Waterproof Boots. I am so impressed with these elevated rugged lace-up booties. They were comfortable right out of the box, they’re easy to get on and off and they provide a little edge to my outfits.

But I also recently ordered the Sorel Lennox Lace-Up Boots and am awaiting their arrival. I got them in blackened brown leather to fill a hole in my wardrobe, but they’re also available in black and nature sandy tan.

Of course you don’t have to have lace-up boots to get waterproof boots. You choose the style that works best for your style aesthetic. And if you don’t live in an area where you need waterproof boots, then skip this category all together.

Of course, you’ll want other shoes in your wardrobe for winter, too. I love my riding boots and my other booties. But the biggest shift we make from Fall Wardrobe Essentials to Winter Wardrobe Essentials is simply adding those all weather boots for wet, snowy weather.


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.

My Double Face Wool Coat by Halogen // Similar coat

See my recent Winter Coat Guide 2020-2021 for a more comprehensive discussion of coats you might need for winter and for more exhaustive shopping options.

Puffer Coat

Honestly I never owned a puffer coat until I moved to Ohio, but now I have two. Last year I purchased this Cole Haan hooded down and feather puffer coat in cashew. I love this coat! I did size up to a large just so it would be plenty roomy to wear over several other layers. Right now it’s 50% off and well stocked in a variety of sizes and colors.

Puffer Coat
Cole Haan hooded down and feather puffer coat in cashew // See the post (from December 2019) for more details

I love having a puffer coat in a lighter neutral in my wardrobe. It’s a fresh site in a sea of black coats, which of course are probably more practical. And I did purchase a black puffer coat for that reason. I wanted something that would go with absolutely everything, pack well and keep me warm. So during the NSale I purchased this Bernardo Packable EcoPlume Hooded Walker CoatThis coat feels lightweight, but keeps me toasty warm. It’s so very soft, too. And it has straps inside that the coat easily packs into.

Bernardo Packable EcoPlume Hooded Walker Coat // See the post for details.

My Bernardo Packable EcoPlume Hooded Walker Coat is almost sold out, but I’ve linked you to similar options in the shopping widget below.

Winter Weather Accessories

Once you’ve determined the colors of your wardrobe, you actually can buy scarves in pretty prints that will coordinate. For instance, I wore this pretty plaid scarf with my pink coat, but it will also work with my black puffer coat. But the safest bet is definitely to invest in a scarf in a pretty neutral that will play nicely with even more.

White and Grey with Plaid Coat
See this post for more details. Similar coat // Scarf // gloves

I have a grey scarf, darker grey fingerless gloves and a grey beanie (not pictured above). I know I can wear these with any of my coats or jackets. I’ve filled the shopping widget below with lots of options in each category.

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’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.

If You’re Visiting from Pinterest…

I hope you’ll take a few moments to look around Dressed for My Day. You might want to…

  • find out more about me here.
  • check out my other fashion posts here.
  • discover the answers to my frequently asked questions here.
  • start with my home page here.
  • take my What’s Your Style Essence quiz here.
  • join the Dressed for My Day community here.
  • follow me on InstagramFacebook and Pinterest.
  • visit my YouTube channel and subscribe to it.

Blessed for My Day

How beautiful that the shepherds decided to draw close instead of backing away when they were told about the birth of Jesus. “Let’s go see!” they said. They wanted to see with their own eyes what God had to revealed to them.

This Christmas let’s be women who draw near, too. Let’s look with our own eyes into the Scriptures and read the amazing story over and over. Let’s ponder what we read and let’s hold it close to our hearts. Let’s think about the words we sing and the candles we light and the advent messages we hear. Let’s draw near and see more clearly this thing which the Lord has made known to us.

When the angels went away from them into heaven, the shepherds said to one another, “Let us go over to Bethlehem and see this thing that has happened, which the Lord has made known to us.” ~ Luke 2: 15

Spread the love
xoxo, Kay
Join the Conversation

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

6 thoughts on “Winter Wardrobe Essentials 2020-2021

  1. Oh dear, I LOVE you infectious, beautiful smile! It makes all your outfits shine! You look beautiful in the pink heather cashmere sweater! But all the outfits look great and also warm! I so appreciate you sharing your faith w us! Merry Christmas!

  2. What a great post. A lot of information here. I love the plaid coat especially and reminds me to pick up some neutral scarves. Sometimes they are the perfect thing to bring together a look. Thst pink coat is amazing and looks amazing on you. Pretty in pink on steroids!

    1. It was from Nordstrom last year and I haven’t seen anything else quite like it. Check the shopping widget though. There are some pretty ones in there. ?