Winter Wardrobe Essentials

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.

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.

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.

Pants

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.

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.

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).

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.

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.

Tops

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.

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.

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

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.

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

A VERSATILE DRESS

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.

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.

Footwear

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

Sneakers

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.

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

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.

Boots

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.

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.

Outerwear

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.

Puffer Coat

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.

Accessories

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.

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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