Casual Winter Outfits

Julie Marshall
by Julie Marshall
15 Minutes

In this post...

Introduction to Casual Winter Outfits

In this post, I will show you seven different casual winter outfits that I wore on a recent (January 2022) trip to Chicago. As some of my readers know, I have a home in the Chicago suburbs where I spend the summers and fall. For most of the winters, Mr. G.Q. and I reside in La Quinta, California, which is about 30 minutes east of the Palm Springs Airport. My mother-in-law just turned 95(!) and we headed back home for her celebration brunch.

Here are the outfits I wore for the days leading up to the brunch. I had three brunches, three dental appointments, three dinners with friends, so I was busy!!! I was delighted to have the opportunity to wear so many cute winter outfits for going out.

When you enjoy all four seasons as much as I do, coming up with casual outfits for winter is a joy! As we are coming to the end of February, I know many of you may be sick of wearing winter clothes and are instead longing for spring. But as I look at the weather for much of the country, winter is still with us. So take a look at these cold weather outfits and see if they don’t inspire you to shop your closet or to take a look at some of the items I am wearing. Many are on sale, so click on the carousels to see for yourself!

Outfit Number One of the Casual Winter Outfits

This was a look I wore going out with dear friends to dinner. Pro Tip: It’s important to wear winter layering outfits when one travels to Chicago in the winter. By this I mean, the white cotton shirt worn under the leopard sweater with the thin cashmere scarf all provide soft, but cozy layers. The same is true of the skinny jeans worn tucked into suede over-the-knee boots.

I should also mention that of course, I wore a heavy tan camel’s hair coat over this look. Pro tip: From living in Chicago most of my life, the best basics to have in your coat closet include a black cashmere or tan camel’s hair coat. They go with everything!

Outfit Number Two of the Casual Winter Outfifs

In this second cute cold weather outfit, I paired a darling gray hoodie with a pair of black vegan leather leggings. The day I wore this for a winter brunch outfit, it wasn’t very cold. So instead of boots, I wore my favorite grayish sneakers.

And as you can see from the flat lay, I added a black puffer coat. I love these for trips because they can collapse into very little space, and then be popped on for a great layer. For jewelry, I wore my stainless steel watch, a bangle, and pearl stud earrings.

What do you think of the vegan leather leggings with the hoodie? They are remarkably comfortable and warm, They’re also a breeze to launder (on cool, inside out, and hang to dry), which I had always wondered about before purchasing them.

Pro tip: Lastly, I wear leather gloves whenever it’s below 50 degrees wherever I am as I have dry skin, and protection is the best way to avoid cracked fingers!

Here is the link for the umbrella print on the wall.

Outfit Number Three of the Casual Winter Outfits

Here I wore a pink cashmere tunic (belted with a black leather belt) over the same vegan leggings from the second outfit and the same black suede over-the-knee boots as in the first outfit. This was a cute winter outfit for going out to with friends. I wore this to dinner and was nice and warm. Pro tip: Cashmere is such a wonderful fabric as it is warm, while typically not very bulky.

I actually forgot to take a photo of the outfit while in Chicago (where I left behind the over-the-knee boots), so here I instead wore these terrific gray suede booties that I have worn a bunch this season both in Chicago and in California. Pro tip: I have always tended toward black suede booties for years, but this year after trying these gray ones, I strongly recommend them as a fun and useful alternative to black.

I added a pink leopard scarf to my neck. This fills in the henley neckline of the tunic and adds a bit of interest to the otherwise simple outfit pieces. Pro tip: Leopard is a neutral pattern that elevates any style of outfit and goes with everything.

Outfit Number Four of the Casual Winter Outfits

A blog on winter outfits wouldn’t be complete without discussing puffer vests. I love puffer vests as they work as the top layer out in California when I go for my walks and they are a lovely layering piece on planes, and under an overcoat when in Chicago in the winter. A vest gives added warmth and pulls together a look (even when the coat is removed.)

In the flat lay, I took a basic white cotton turtleneck and paired it with boyfriend jeans and the gray gym shoes from outfit number two. One day I layered on the puffer coat with a black glen plaid scarf, while on the other day, I wore the vest under a coat with a black and gray foulard scarf. Pro Tip: One of the easiest ways to look stylish while wearing cold weather outfits, is to add a scarf! I love scarves as they add interest, warmth, and texture to any winter outfit.

Outfit Number Five

Here in this winter outfit idea, I paired a black cashmere v-neck sweater with an orange-red and black plaid shirt. Again, I wore the gray booties with the skinny jeans. To fill in the neckline, I added a multi-stranded necklace. Pro tip: Be sure to pop out and fold back your cuffs as it looks way more elevated this way. I also turned the bottom of the sweater under so that the “tail” of the shirt would peek out as well.

Outfit Number Six of the Casual Winter Outfits

Here is a casual winter outfit idea that was a winter brunch outfit. I took my mother-in-law out for breakfast at the pancake house. It was a sunny day and this red cotton turtleneck was comfy under the black puffer vest with a red bandana at my neck. My skinny jeans again made an appearance with my gray sneakers. Over this, I wore a tan camel’s hair coat, worn open, due to the temperature.

Outfit Number Seven of the Casual Winter Outfits

In this last of seven winter outfits, I paired my boyfriend jeans with a navy striped turtleneck and the black puffer vest. The gray booties worked well with the jeans as well as the black and gray leopard scarf. The most fun piece of this outfit was a fake fur vest. I have had it for years and I love it!

Again, I took this flat lay photo in Chicago but forgot to take the “finished look” there so you see either the over-the-knee suede boots or the gray suede ones work beautifully.

So folks, there you have it! Seven casual winter outfits. Which one is your favorite? Did I inspire you to shop your closet for some fun looks? Many of these items above are on sale as it’s considered late in the winter season for retailers. So click on the links and see if you can score a great winter deal!

Happy Shopping!


Dr. Julie

PS Here are a few more posts for you to enjoy:

Delicious, Easy, and Quick Irish Soda Bread

Black Blazer Outfit, Six Different Looks

How to Style a Black Jumpsuit Wide Leg

Wedding arms and other tips…

The author may collect a small share of sales from the links on this page.

Julie Marshall
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