Winter Wardrobe Essentials – 19 Pieces For 300 Different Outfits

In this post, I am going to be sharing with you 19 winter wardrobe essentials that everyone should have in their closet. I am a basic kind of gal…(as you may have concluded from the title of this blog). I try to invest in quality, timeless pieces that will match just about anything so I can keep my closet minimal but my style evergreen. In this post, I will show you the wardrobe essentials that alone, will make you almost 400 different outfits. The pieces I will be showing you will mostly have a winter flair to them but all of them can be worn for at least one other season as well. Every one of these items can be paired with any of the other items on this list, giving you the 288 total different combinations.

Essential Winter Shirts

1. The Neutral Cashmere Sweater

This warm winter staple whispers elegance and matches just about anything. I love the VINCE funnel neck sweater because it is unbelievably soft, warm and it looks flattering on almost anyone. As someone who has sensitive skin, I struggle with cashmere blends as they often itch and irritate my skin. With this sweater, I do not have any problems—I will say, it runs a bit large so I suggest going one size down. Wear this as is or layer it on top of a collared button-up and it will keep you warm and cozy whatever the occasion may be.

VINCE tan funnel neck super soft cashmere sweater

2. A Simple Long Sleeve Bodysuit

Bodysuits were a somewhat recent discovery for me and I am unsure how I made it this long without them. Get a neatly tucked appearance without the lumping in your pants and extra time needed to re-polish yourself after going to the restroom. A black bodysuit is simply a wardrobe essential for everyone—perfect for multiple occasions, and easy to match with almost everything. You can easily wear this in the fall and in the cooler spring days as well. I often wear the Naked Wardrobe bodysuit or the Leith V-Neck one pictured below.

Leith long sleeve v neck bodysuit, matches everything and perfect for every ocassion.

3. A Black Turtleneck

A black turtleneck is one of my favorite winter wardrobe essentials that is so easy to wear (it goes with almost anything) and is a classic piece that you can keep forever. Chances are, you already have one in your closet, but if not, now is the time to get one. My well loved one, is the French Connection turtleneck pictured below.

In case you didn’t already notice, I LOVE turtlenecks in the winter. They not only provide you extra warmth but they also are a super simple way to look chic and put together. A good turtleneck can keep you cozy while working from home and also help you look put together for those early Zoom meetings. Also, I don’t know about you but during the winter, my skin becomes almost ghostly looking. I usually have a foundation that is a shade or two darker than my natural winter color (or lack there of) so if you’re wearing the turtleneck, you can opt for the darker shade and make yourself look a bit more tan.

French Connection cashmere blend black fitted turtleneck.

4. A White Turtleneck

I’m sorry but whoever said you can’t wear white after labor day was wrong….while I agree, you can’t wear some white materials in the winter, I think having some white winter pieces can help you add some brightness to your outfits. White sweaters and warmer tops are also a great way to transition into spring clothes. Therefore, this white turtleneck made the cut for my winter wardrobe essentials. You’ve already heard why I love turtlenecks so much, just as you need a black one, you need a white one as well. The favorite one that I own is the French Connection Jasper Vhari High Neck Sweater.

French Connection long, white oversized sweater.

5. A Trusty Black Blouse

Another winter wardrobe essential you should have in your closet is a good black blouse . This should be something you can wear for a nice dinner to spice up an otherwise casual outfit. The style of the blouse is a matter of personal preference but it should be a tried-and-true piece that makes you feel your best. Pictured below is the 1.State Smock Detail Button Up which is perfect for a business casual dress code or a date night.

1.State smock detail black flowy blouse

6. A Cream Textured Crewneck

Nothing screams the holidays like a cute, textured cream sweater. The one below is from Lulus. This cream crewneck is a great item to pair with jeans for a casual night out or a daytime outing on a cold winter weekend. The details and texture on the sweater are a great way to spice up an otherwise basic item. Cozy up by the fire with your family during Thanksgiving or Christmas with this wonderful winter essential.

Lulus cream textured knit crewneck sweater

7. A White Button Up

This is truly an essential that is meant for every season. By itself, I wouldn’t consider a white button up a it a winter item, but it’s perfect to layer under a sweater for a little extra flair. Pair with black pants and a warm oversized sweater for the perfect weekend outfit.

Classic oversized white button up for women

8. Cropped Sweater

With the high-waisted pant trend that is still at it’s peak, a trusty cropped sweater is a must-have. Longer sweaters can sometimes make you look wider than you naturally are so the cropped style is a great way to accentuate your shape in a flattering way. Pair with the high waisted pants and a thick belt for the perfect weekend winter outfit. I am wearing the TopShop Back Crop Turtleneck.

TopShop nude cropped sweater turtleneck

Essential Jackets

9. Black Sweater Blazer

Warm, practical and chic, this J. Crew Collarless Sweater Blazer is a must-have for your winter and fall wardrobe. I find myself grabbing this almost every time I leave the house. It matches everything and is perfect for almost every occasion—be it a trip to the office or a weekend dinner. This is another timeless piece that will never go out of style.

J. Crew black collarless sweater blazer

10. Tweed Knit Blazer

A tweed knit blazer is a great way to dress up an otherwise casual outfit. I love that the material always feels of good, durable quality and it makes an outfit look more elegant and though out. It’s the perfect outer layer for fall, winter or spring, and great for a weekend outing or a day at the office. I love the tweed knit blazer from Helene Berman, it pairs well with everything and is built with quality and attention to detail. In the photo below, I am wearing the ASTIR one in the photo below. This blazer is a bit more dressed down than the Helene Berman one, but both are great for different reasons.

black and white tweed knit blazer with a button in the center

11. Warm Fuzzy Jacket

Unfortunately, I had a hard time finding the exact one that I have, it seems that the tan sherpa jackets are on low supply these days. I found one that looks nice. However, when I say that my sherpa jacket was well-loved this season, it is an understatement. This jacket went with me everywhere. Despite living in North Carolina, we had a pretty cold winter this season and this jacket was enough to keep me warm and cozy at all times of the day. I swear I would get compliments on it wherever I would go and it honestly looks great with just about anything.

tan sherpa button up winter jacket

12. A Slouchy Cardigan

A good, comfy cardigan is just what you need to complete your winter wardrobe essentials. This one is my favorite. It’s under $40 and you can get it from Amazon. There are a wide variety of colors, I have the beige one. It’s super comfy and matches almost anything.

Essential Pants

13. Black and White Plaid Pants

I got these Rag and Bone plaid pants in a TrunkClub box and they have really elevated my style. Therefore, they had to be added to this to the list of winter wardrobe essentials because they really are great—so stylish and comfortable, not to mention almost 70% off! I have been trying to stop myself from always gravitating toward jeans and these stylish pants almost always are a great substitute.

Rag and Bone grey plaid pants

14. Dark Wash High Waisted Jeans

I tried to omit jeans from this post because, I am trying to become less denim-dependent. However, you cannot have a complete winter wardrobe without dark wash, high waisted jeans. These can easily be dressed up for a night out or worn to run errands in a more casual setting. J Brand is by far, my favorite jean brand but I really like these Madewell 9-Inch Mid-Rise Skinny Jeans, which are a fraction of the price. They are, as the brand implies, made well, and despite the “mid rise” name are more like a high rise fit. Being on the taller side (5’8″) I have a hard time finding jeans long enough to cover my ankles but these ones do the trick!

15. Grey Cropped Slacks

I am never sure if I should spell “grey” with an “a” or an “e” so you will have to forgive me if I used the wrong version. These were another item I received in my Nordstrom Trunk. A simple substitution for denim that can take your outfit to the next level, this beautiful grey color easily pairs with other neutral items and is great for an elevated weekend outfit or a day at the office. They are also insanely comfortable which makes them that much more appealing. Sometimes I wear these even just working from home because they make me feel put together but also are nice to lounge in all day at my desk. I paid full price for them, but these Club Monaco Cigarette Pants are now almost 60% off!

Club Monacco grey cigarrette pants

16. Black Jeans

Hopefully, you already have these essential pants already in your wardrobe. But in case you don’t, let me tell you how much I love these J Brand black jeans—which are currently 50% off! They are the most comfortable jeans I have ever owned and are extremely flattering. A hardy pair of black jeans are the staple that will go with any top, any shoe, and make you look more polished than your typical blue jeans.

Hardy black high waisted jeans

Essential Shoes

17. Black Sneakers

These Cole Haan Grand Ambition Sneakers have become my new go-to shoe all winter, which is why I am adding it to my winter wardrobe essentials list. These shoes are perfect for running errands, shopping, going for a walk or even dressing up. The gold plate on the toe and the pointed shape make them look elegant and chic while giving you the comfort of a traditional sneaker.

Cole Haan Women's black grand ambition sneakers.

18. White Sneakers

A good pair of white sneakers are a staple for every season. They look great with just about everything and give you that comfort that is suitable for whatever activities the day may involve. White sneaks are the perfect way to add a crisp brightness to your outfit. My go-to pair are the Cole Haan Grand Pro Tennis Sneaker. In case you haven’t already noticed, I am a big fan of Cole Haan shoes. The brand always delivers quality and comfort.

Cole Haan women white sneaker

19. Black Leather Booties

And last but certainly not least on my list of winter wardrobe essentials, we have the black leather bootie. You really can’t go wrong with a quality black leather bootie. They are great for a weekend outing or to wear into the office. Your winter closet is not complete without a pair of these bad boys. I have owned probably 15 different pairs of black booties over the years and the Frye Melissa Shooties are by far the best. They are a soft leather that makes them extremely comfortable without really needing to break them in. I have walked 15 miles in New York in these boots (in one day) and didn’t have so much as an ache in my feet. They have held up for me extremely well. I am also pretty tall so I love that the heel is not overwhelming.

Disclaimer: While this post is not sponsored in any way (I chose to feature and paid for all of the products myself), I do make a small commission on the affiliate links above. If you chose to purchase any of the items through the links, I appreciate your support in that way!

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