Fall/Winter Fashion

Winter Wardrobe Essentials 2020-21

Greetings, friends! It’s coming out a little later than usual this year, but I’ve updated my Winter Wardrobe Essentials for 2020-2021!

Winter Wardrobe Essentials 2020-2021

Everyone’s winter wardrobe essentials will vary based on climate, but I’m going to write this post assuming we’re talking about cold weather climates. If you’re in a warmer climate, my Fall Wardrobe Essentials might be more relevant for you.

As always, I encourage you to take your lifestyle and personal needs into consideration when making purchasing decisions to build your wardrobe.

I spend most days at home, so my personal winter wardrobe essentials are heavier on casual wear and lighter on dressier styles, but I still try to make sure I have clothes for any occasion that might crop up, so I’m not scrambling when I get a last minute invite.

Also be sure to consider cost per wear when deciding how much to allocate to each wardrobe item, so you can make the most of your budget.

2020/21 Winter Wardrobe Essentials

1. Classic Wool Coat

plaid coat // sweater // jeans

I’m starting my list this year with a classic wool coat, even though I wear my puffer coats a lot more. That’s because a classic wool coat will take you just about anywhere — from the office to dinner, from the grocery store to the shopping mall, and anywhere in between.

It’s the perfect piece of outerwear to top off a work wear look or a sweater dress for church, or you can throw it on over jeans and a casual sweater and look instantly chic. You can even wear it to level up your favorite workout gear.

A classic color like grey, camel, or black is always a safe bet, but don’t rule out fun colors like red, pink, blue, or even plaid! Choose a classic style, and it will last you many years.

2. Winter Boots


You may want a variety of boot styles in your winter wardrobe, but the one that is essential for cold climates is a good pair of snow boots.

I did a winter boot review not too long ago, and I compared a bunch of different styles from Sorel as well as a few other brands. Most had that hiker boot or sneaker boot vibe going on, but Blondo and Aquatalia make dressier styles that are also weather proof.

Color-wise, I like to have a variety of neutrals — black, grey, and cognac are all great colors to have. If you only choose one, consider what works best with the other items you will pair with them.

3. Scarves

scarf // coat // sweater

One question I get a lot this time of year is, Are scarves in style this year? So of course, I wrote a post about it!

As I said in that post, scarves as an accessory category never go out of style, but they may wax and wane in popularity, and scarf styles do go in and out of vogue. Right now, we’re definitely seeing a shift away from infinity scarves and those big square plaid blanket scarves that were all over the blogs a couple years ago.

However, a winter scarf as a cold weather accessory is always appropriate, and it’s also a great way to add interest to your winter outfits.

You can find beautiful scarves at just about any price point, and I linked up a few of my favorites below.

4. Puffer Coat

coat (I sized up to a medium) // similar turtleneck // sunnies

Whereas you can wear a wool coat with both dressy and casual looks, a puffer coat is pretty much always a casual wardrobe piece, and they come in all different lengths and styles.

If you live in a cold climate, you probably need at least one full-length, heavy-duty puffer for the coldest days and a shorter option for milder winter weather. Just make sure your puffer coat is waterproof, so it will hold up to all kinds of inclement weather.

5. Tech Gloves


My fingers freeze in the wintertime, but I also want to be able to access my smartphone when I’m out and about, so tech-friendly gloves are a must. U|R makes my favorites; they work so well, and they’re beautiful too.

Other good options are fingerless gloves or convertible mittens. My photographer, Alison, always wears fingerless gloves so she can operate her camera.

6. Beanies

hat // vest // turtleneck // sunnies

Beanies are cute and very much on trend right now, and they also work really well to keep your head warm when it’s super cold out.

I admit, I don’t wear one very much — usually only for exercising in the cold — but when you need it, you need it.

FYI, Anthro has 50% off everything right now, and they have some really cute beanies and scarves!

7. Sweaters

casual outdoor dining outfit for fall starting with a simple camel sweater

sweater (wearing the camel, size S)

A good quality sweater can work for so many occasions. Wear it to work with trousers or a skirt, wear it on the weekend with jeans and sneakers, wear it on a date night with jeans and heels… Pay attention to neckline and choose a style that is flattering for you.

Sweaters and jeans are my daily uniform in the fall and winter, and I have a LOT of sweaters! I like to have variety of necklines, and I’m a huge fan of cashmere. No other sweater fabric is as soft and warm.

Of course, some people are allergic, which is such a shame! But if you aren’t, there are some really good deals on cashmere right now. It’s a great time to add one or two to your winter wardrobe.

I’m actually working on a cashmere sweater comparison post, so stay tuned! Meanwhile, here are some of my favorite cashmere and non-cashmere options:

8. Jeans (No Rips, Brrrr…)

scarf // jeans // booties

Jeans are a 3-season wardrobe staple, but in the wintertime, I usually stay away from rips and holes. It’s usually too cold for that, and they look rather incongruous worn with sweaters and boots.

Straighter styles are making a comeback right now, but I find skinny jeans the easiest to wear this time of year, especially with taller boots. It’s totally a matter of preference, so wear what works best for you.

Most women will want a variety of styles and washes, and if you don’t have any, I would definitely recommend adding grey or black jeans to your winter closet. They’re highly versatile — more so than blue jeans, if you ask me, and they’re very on trend at the moment.

9. Sweater Dress

I love a sweater dress in the wintertime. Pair it with tights and boots or booties for a look that’s chic and effortless. Wear it to the office, to church, on a dinner date, or for lunch with the girls.

I recommend wearing a slip under your sweater dresses. It helps them skim the body and not cling to any lumps and bumps, and it also prevents them from sticking to your tights. And that leads me right into #10…

10. Good Quality Tights

True confessions: I hate tights, but sometimes they’re a necessity. Especially with the aforementioned sweater dress.

I highly recommend Spanx tights because they do double-duty as shapewear, plus they’re nice and thick and opaque. (I have this pair in black and grey; they’re also at Nordstrom and Amazon.)

11. Tall Boots

sweater (got mine on sale) // jeans // boots

Knee-high or OTK boots are your warmest footwear option, which definitely keeps them as one of my Winter Wardrobe Essentials, even though we aren’t seeing them as much this year.

They work best over skinny jeans, but they’re also my favorite for wearing with sweater dresses in the winter. Ankle boots can work with the right style of dress, and if they suit your personal style aesthetic, but for me personally, I prefer a classic knee boot with my dresses.

I hope this is helpful! Of course, it’s not an exhaustive list, but it should be a good place to start.

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3 thoughts on “Winter Wardrobe Essentials 2020-21

  1. Thank you for this Essentials style guide! I certainly have at least one of everything, but I love seeing how you put pieces together for a fresh look. This year, I’m not even wearing all my holiday clothes, so sad! I will have to pack away a lot for next year! It’s funny when I overdress for the grocery store because I really want to wear my beautiful tartan plaid sweater! HA!!!

  2. I highly recommend Heist tights. My daughter, who is 6′ tall told me about them and they are the first tights I’ve ever found that are comfortable. I’m only 5’7″ but have long legs. I don’t have to keep yanking these up!

    I ordered the hooded leather jacket and I love it– though it feels tight in my upper arms so I’ve reordered a size up. Thanks for letting us know it’s on sale, Jo-Lynne! A Christmas present to myself. Wait. I also ordered the Sorel Lace boots for myself for Christmas. lol.

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