2019 Winter Wardrobe Essentials

It feels like winter has been here for a while, but tomorrow is officially the first say of the winter solstice, so I guess it’s time to update my Winter Wardrobe Essentials for 2019!

(If you’re on Pinterest, I would love for you to pin the image above so others can find this post. Thank you!!!)

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 you build your winter wardrobe, I also encourage you to take into consideration your lifestyle and personal needs. 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.

When I’m putting together a post like this, I usually start with shoes. Shoes are the item in my closet that changes most dramatically with each each season. For example, I will wear short sleeved tees and white jeans all year round, but I definitely put away my sandals and open toe booties and pull out my snow boots when cold weather arrives.

So let’s get right to it!

Here’s my list of 2019 Winter Wardrobe Essentials, and I’ll also talk about what styles and colors are trending in each category.

2019 Winter Wardrobe Essentials

1. Tall Fashion Boots

I love ankle boots in the fall, and I still wear them some in the wintertime (see #3) but I find myself gravitating more often to my tall boots because they’re so much warmer. I like both knee-high boots and over-the-knee boots, and I try to have some that are more casual and others for dressier looks. I’ll link up a few examples, but there are so many possibilities out there. Feel free to use these ideas to shop your favorite retailers.

Also, for winter, remember that suede isn’t very good in messy weather. Leather will be much more versatile if you live in a climate that gets much rain and snow, unless you buy suede that is weather proof. Brands like Blondo and La Canadienne do a great job with weather-proof fashion boots.

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.

Style Tip >> When tucking pants into knee-high and OTK boots, I prefer to wear “legging jeans” or “super skinny jeans” — especially with the tighter OTK boot styles. You definitely don’t want your jeans bunching up at the top of your boots.

2. Snow Boots or Rain Boots

If you live in an area that gets a lot of snow, you probably want snow boots in your wardrobe. I admit that I haven’t always had snow boots because a good leather riding boot can be worn in almost any condition you would need a snow boot for, but snow boots definitely keep you warmer than riding boots. If you’re in a warmer climate that doesn’t get much snow, rain boots would certainly suffice. When it’s cold, you can wear thick socks, or better yet, Smartwool inside.

3. Ankle Boots

While my ankle boots tend to take backseat to my tall boots during the colder months, there’s still a place for ankle boots in the wintertime. Ankle boots are great because of their versatility. They still keep your feet out of the mud and the muck, but you can wear them with just about every style of jeans and pants. They look great with skinnies, or if you prefer a bootcut or straight leg pant, you can wear them over top of your ankle boots. The sock issue gets tricky with booties and skinny jeans in cold weather, but you can wear socks with some styles. I try to match the sock to the boot so it isn’t as noticeable. These are my favorite socks to wear with ankle boots.

4. Skinny Jeans

I realize that not everyone looks best in skinny jeans, but they’re pretty much a necessity if you want to tuck jeans into tall boots. (If you’re trying to balance out a carrot or a pear shape, wear a bulkier boot or shoe with your skinny jeans and wear a lighter color on top.)

Or of course, you can also wear your tall boots with skirts and dresses and wear your straight or bootcut jeans with booties, but I had to include skinnies in my winter essentials because I pretty much wear them every day. As I said above, I prefer the “legging jeans” or “super skinny” styles because they’re easier to fit inside my tall boots.

5. Classic Wool Coat

A classic wool coat will take you anywhere — from the office to dinner, from the grocery store to the shopping mall, and anywhere in between. You can throw it on over jeans and a casual sweater and look instantly chic, and you can also wear it over your favorite workwear looks. A classic color like grey, camel, or black is always a safe bet, but don’t rule out fun colors like red and lavender.

6. Puffer Coat

A puffer coat basically takes you anywhere a wool coat can’t. Or, maybe it’s the other way around. Anyway. I think both are winter wardrobe essentials. Just make sure your puffer coat is waterproof, so it will hold up to all kinds of inclement weather.

Whether it’s short or long and lightweight or heavy duty depends on your climate and lifestyle. I have a shorter, lightweight quilted jacket for milder weather and a long, heavy duty puffer coat for the coldest days. That is in addition to a long camel reefer coat, a grey wool cocoon coat, and a red wool peacoat. #ilikecoatsandicannotlie

7. Sweaters

This sort of goes without saying, but I can’t really write a winter wardrobe essentials post without including sweaters, can I??? And while we’re at it, why don’t we make it cashmere? Go big or go home, right?

Truly, though, I think every woman should have at least one cashmere sweater in her wardrobe. They’re not as spendy as they used to be, and you can usually find good sales during holiday season.

A good quality classic 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.

Turtlenecks are having a moment, which is nice because they’re so practical for those of us living in colder climates, but I like to have some v-necks as well. I personally find them most flattering, but if you’re smaller chested, you might prefer a crewneck style. I’m a pullover kind of girl, but it’s nice to have a couple cardigans to mix it up. I rounded up an assortment of my current favorites below.

8. Layering Tees

They’re not fun to buy, but they’re necessary. Sometimes I wear a thin tee under my pullover sweaters for additional warmth, and when I wear cardigans, I prefer a long-sleeve tee underneath. Blouses and flannels can be nice too, but I find layering them under a sweater uncomfortable.

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.

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 also just discovered Hipstik tights — they’re designed to be comfortable and never slide down, and I have to say, they do just that. I have these opaque black tights.

I also 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.

11. Cozy Scarf

Blanket scarves are on their way out, but more traditional scarves are here to stay. I, for one, am very happy about this! The big blanket scarf draped over the front kerchief-style really isn’t that practical, but I’m all for draping a long, cozy scarf around my neck when I’m outside.

Infinity scarves are even easier still, as they take all guesswork out of styling, but I think they’re also beginning to look dated so I recommend sticking with the more traditional styles unless you have one you absolutely love. Then by all means, go for it! At the end of the day, you should wear what you love.

12. Tech Gloves

My fingers freeze in the wintertime, so I always need gloves, but I want to be able to access my iPhone so I have several pairs of tech-friendly gloves.

13. Neutral Carryall

You really need this all year ’round, but I felt like this list wasn’t complete without a go-to handbag. I will always prefer a tote for daily use, although I also like hobo and satchel styles.

I’m all for having a few colorful handbags in my closet, but I think your go-to bag should be a neutral. Consider grey, cognac, brown, or black, depending on what colors you tend to wear the most.

I’d love to hear your thoughts! What would you add to this list? I realize it will vary a bit for everyone, but I think this is a pretty good place to start.

There are a TON of great sales going on right now, so hopefully you can take advantage of some of those as you round out your winter wardrobe!

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