7 Casual Winter Outfits That Work Every Time For Petites

woman wearing black faux leather leggings and a black sweater with leopard trim for a casual winter outfit 01

This is the time of year that so many of us get tired of wearing our winter clothes, me included. We are just ready to move on to the next season. Also, retailers are starting to tease us with new arrivals, but it is just too cold to wear them for quite a while. Sometimes we just really need to look into our closets and see what’s there. I’m going to share seven casual winter outfits that I find work for petites (like me) every time.

See if you have these things in your closet too. If not, then you might want to consider some of the things “essentials” to have when winter rolls around again.

Before we dive into casual winter outfits that always work you might want to check out some other posts that I have written that relate to winter fashion and being petite.

This post may contain affiliate links; if you click on a shopping link or picture and make a purchase, I may receive a small commission (at no cost to you), so thank you. Also, as an Amazon Associate, I earn from qualifying purchases. I appreciate your support.

7 Casual Winter Outfits – An Idea A Day

I hope this inspires you to go into your closet, check out what you have, and then make a few new outfit combinations. It’s a great time of year to take inventory, so to speak, and see if you need to replace some things while they are on sale.

Faux leggings with a sweater

Ok, I think that faux leather leggings are something that every woman wears. Now we are lucky that Spanx makes them in petite sizing. Not only do they offer the original, but now they have the pantent leather and the moto version. So if you love your leggings you now have choices. You can pair any of these with sneakers, boots, or loafers.

Also if you really need to stay warm, then add a pair of these fleece-lined leggings to your wardrobe. They will do the trick.

One of my favorite cozy winter sweaters is from Dudley Stephens. I prefer the Park Slope because I can also tuck this length into jeans. If you like a little more coverage over your back side, then you might want to consider the Cobble Hill. These fleece launder beautifully and you can always find a color option that looks great on you. They always offer their tops in 10 or more colors each and every season.

Sweater blazer/coat with column of color

A sweater blazer is a great layer in the winter. J.Crew has been making the Juliette and Emilie or similar for a while now. They aren’t as dressy as a true blazer and you can choose what type of layering you need for the day. It could be a t-shirt, a turtleneck, or a striped shirt. Probably the easiest way to wear one of these is with denim, all white, or all black.

I know I pull my version of this sweater blazer out from time to time and come up with so many different ways to wear it. Truly a closet classic. The other thing is that it packs beautifully for trips. I just turn back the sleeves so that they are not too long or I push them up on this type of sweater blazer.

sweater dress

There is nothing easier than throwing on a black sweater dress with a pair of booties or knee boots. Add a few accessories and you are good to go. You can easily dress them up or down, depending upon your choice of accessories.

It is difficult to find sweater dresses in true petite sizing. I am always on the lookout because they are just a great staple. The dress that I have on in the photo above works for petite bodies because it is not too long. I wear it with boots and booties. It’s so good that I also have it in the brown option.

If you are looking for a shorter black sweater dress, then this is a great option. Tommy Bahama dresses tend to run petite-friendly year-round. They are a go-to for me in the summer for linen dresses.

If you are looking for a cashmere sweater dress, then my favorite option is always Aqua at Bloomingdales. They always have a good selection of styles. I really like this shorter fit and flare and this turtleneck dress. Both would be great with tights and boots to stay warm this winter.

Faux fur vest with sweater and jeans

One of my favorite things to wear in the winter is a faux fur vest. Since I live in the south and many days our weather is rather mild it’s really all you need. The other great thing about them is if you are in and out of a car they are not so bulky. Any faux fur vest will elevate a simple sweater and jeans.

I wear this vest so much that I now have it in black and brown. Here are some fun vest options to add to your coat closet.

Joggers With A Cute Jacket Or Sweatshirt

Who would have thought that joggers would become so popular and worn in so many different scenarios. You see the style in everything from soft fabrics to sequins. For an everyday outfit, I love my Vuori joggers. This is probably one of my most frequently worn casual winter outfits. I work from home and sit at my computer for several hours a day so I like to be cozy and comfortable, but still look nice if I go out to run an errand or meet a friend for coffee/lunch.

These pants are so soft that you feel like you are in your PJs, but with a cute jacket or sweater blazer like I mentioned above they become a true casual pant. Just don’t put your gym sneakers on with them when you want to wear them casually. Try a few different scenarios.

I also find that these Zella joggers will work for my petite body. We can also always count on Athleta to give us a few petite options for joggers. I really like this mid rise style with the flat waist band.

Black pants and a sweater

Sweater (similar color, same sweater | Pant

Probably the easiest standby any of us could ever have is a great-fitting pair of black pants. Or maybe two or three. I have been enjoying these super stretchy back zip pant all winter. The other pant that has been on rotation this winter is this straight-leg pant that is in a four season stretch fabric. It’s not too heavy and not too light.

Now if you are looking for a pair of black pants that will make your legs look longer than you can ever imagine this pair of flare pants is the ticket. I am wearing them in the photo above with the white coat.

Comfortable, Fun Pajamas

Pajamas (use code SASFORSHORT for 10% off sitewide)

Who doesn’t love a “PJ all day” day every once in a while to stay cozy in the winter? I think they are the best days when it’s snowy or icy out. My idea of one of the perfect casual winter outfits for staying inside and cozy. You’ll laugh. I will get showered, fix my hair, put my makeup on, and then put my pajamas on with a pair of thick socks with rubber grippers on the bottom.

PrintFresh pajamas are a favorite of mine and they make petite sizing in some styles. Their fun colorful prints are so unique. A friend of mine refers to them as “wearing a work of art”. The patterns are so good. The good news is that you can use my code SASFORSHORT for 10% off any order from PrintFresh.

When it comes to flannel pajamas in petite sizing you can’t go wrong with LL Bean. Once you know which of their styles really fit you you are in luck. They make many of the same styles year in and year out.

Now as for my socks, I love these Merino wool socks. They are a little pricey, but once you wear a pair of them you will understand why I have several pairs. If it’s really cold, then I pull out these soft slippers with rubber grippers. See a pattern here with the grippers?


Thanks for stopping by my blog today. I hope this inspired you to find some new combinations in your closet for some casual winter outfits or to find some good staples for your closet that are on sale. It’s such a good feeling to have basic pieces that we can easily pull together so that we feel put together.

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