Soft Surroundings for a Cute, Comfy & Cozy Holiday Season

November 11, 2026

The holiday season is HERE and I couldn’t be more excited. To me the holidays are all about cozy time with family and friends, and Soft Surroundings has so many cute and comfortable looks exactly right for the kind of holidays I love.

Thanks to Soft Surroundings for gifting me this cute, cozy, and comfortable outfit for the holiday season!

Shop this Look!

While some gals are pulling out all the stops with sparkle and glam, I really prefer a more comfortable approach to the holiday season. This cute red and black Had Me at Plaid dress is warm and oh so comfortable. With a generous flow to the dress, you can eat all you want without having to even think about sucking in your tummy. Ha! It even has pockets. I’m also wearing a Shelf Bra Cami underneath for a bit of extra modesty. Continuing the comfortable vibe, these Spring Step Zaya Riding Boots are super soft and easy to wear for a full day of cooking, decorating, or walking around looking at lights, or whatever else the holiday might bring. But there has to be a bit of sparkle to a holiday look, right? I added that with a Suzette Snowflake Charm necklace, something more maximalist than I usually would go for, but hey, tis’ the season! Here’s a short video with all the shopping links!

Check out this look and other Soft Surroundings offerings this holiday season. And let me know, do you tend toward a comfortable holiday wardrobe or something more glam? Or a bit of both? Let us know in comments.

Also on the blog recently, this cute fall outfit for a coffee date and these cute sparkly slip-ons would be a cozy addition to a holiday look!

Love effortless and flattering outfit ideas? Let’s stay in touch. You can follow me on IG, sign up for my newsletter and/or follow me on the free and fun LTK app for exclusive content (like Get Ready With Me videos, fun collages showcasing trends, sales alerts, and more!

Fun & Fashion,

Dawn Lucy

About the blog: Fashion Should Be Fun is just me talking to you! With trial and error, I’ve learned to create a wearable, workable wardrobe that really suits me and my lifestyle and now I want to share that with you. Follow me for effortless, minimalist style, outfit ideas, and honest clothing reviews. I’m age-positive, body-positive, and having fun with fashion and life!

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