Plus Size Winter Casual Outfits

Two plus size winter casual outfits with basic and neutral pieces that can be used repeatedly throughout one’s wardrobe. 

And chances are you probably have these in your closet.  But if you don’t, you’ll find plenty of uses for them. 

Both of these looks are the same except that the first has leggings and over-the-knee boots and the second has boyfriends and booties.

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Plus Size Winter Casual Outfits

Plus Size Winter Casual Outfits - Plus Size Neutral Sweater - Plus Size Fashion for Women - Alexa Webb - #plussize #alexawebb

My Favorite Ponte Leggings

While any ponte leggings will do, I wanted to mention my favorite ones.

These leggings are stretchy enough to be comfortable but sturdy enough to maintain their shape. 

And they are thick enough to look smoother than a typical legging.  

Many readers have emailed me to say how much they love these leggings as I have been recommending them for years now!

However, if you are petite, try these.  For tall, try these.

Plus Size Tunic-Length Button Down

As I mentioned in a previous post, if you are in need of a button down shirt, which I think every woman should own, I highly recommend this customizable button down shirt from eShakti

Aside from the fantastic price and amazing quality, if you select the ability to get it customized and custom sized, for less than an additional ten bucks, you will have the best fitting garment you’ve ever had. 

I have ordered custom sized clothing from eShakti and was able to take all of the necessary measurements by myself. 

You can also choose the overall length and length of sleeve.  In this case, I’d order the “mid-thigh” length to wear with leggings.

Plus Size Winter Casual Outfits – Leggings

Plus Size Winter Casual Outfits - Plus Size Leggings, Wide Calf Over-the-Knee Boots - Alexa Webb - #plussize #alexawebb

Shop the Look

This second look is just the same with some neutral taupe booties and boyfriend jeans. 

Watch your proportions, you may have to wear a shorter button down with cuffed boyfriend jeans. 

You can read more about proportions here.

Plus Size Winter Casual Outfits – Boyfriends

Plus Size Winter Casual Outfits - Plus Size Neutral Sweater, Jeans, Booties - Plus Size Fashion for Women - Alexa Webb - #plussize #alexawebb

Shop the Look

Plus Size Boyfriend Jeans {sold out} (similar, less $ similar)

Booties (similar/wide, similar, less $ similar, less $ similar, less $/wide, less $/wide)

For more outfit inspiration check out my Pinterest boards and my Instagram!  Oh and please “like” my blog on Facebook!

Disclosure: This post may contain affiliate links, which means if you click on or purchase through certain links, I may receive a small commission.

12 thoughts on “Plus Size Winter Casual Outfits

  1. Would you say your favorite Ponte Leggings are sized normally? If I normally wear a 18/20 in most pants what would you recommend?

    1. They are true to size, here is the size chart. Although they’re leggings, they don’t have as much stretch as you might think. So if you lean towards a 20 or have large hips/thighs, I would go with the 20.

  2. This is really gorgeous. It’s a chilly morning here in Blighty (England) and I am definitely going to be pulling this out of my wardrobe today! Thank you for the inspiration ?

  3. Hi Alexa,
    You’re favorite ponte leggings are on sale today for $29 at Eloquii. Just ordered some, as well as a couple of dresses that were a steal. Also just bought your favorite jeggings from Torrid. Really nice fit and comfortable. Thanks for the recommendations!

  4. Hi I love a thick legging and I only found one that “used to” make them by 90 Degree. Are these thick? Hard to explain but the ones I love hold in all my jiggles. I have tried so many and can not find any like them. Also I went to the site to have a custom shirt made and they say it is out of stock. How can it be out of stock if it is custom? I am confused.

    1. Hi Mary,
      The leggings are very thick ponte knit. They have stretch but are firm to hold everything in.

      As for the custom shirt, sometimes they discontinue things or only offer them seasonally. It could just be that they are out of the fabric. I’m not sure. I hope they bring it back!!!

  5. I ordered the sweater and love it! It is on sale now!!! Only thing is that it is much darker than the photo. It is not a light cream, it is a lot more brown/gray! I did the white top under but as the day wore on was thinking next I would probably use the jean shirt I got from the same company!!!

  6. I love your suggestions. So glad I found you. For those of us with graying hair, ideas for
    coloring would be great and silver jewelry maybe?

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