A woman in a cozy sweater leaning on the arm of a couch

Last holiday season, I wish someone had told me to soak it all in. I would have hugged everyone a few seconds longer. I would have eaten more cookies at my family’s annual cookie decorating contest. I would have stayed at all the gatherings until I was the last one there and the host was giving me all the cues to leave. 

If I had time traveled to 2020 this time last year, I wouldn’t have believed my eyes. Virtual holiday family gatherings? I still can’t believe sometimes that this is the reality of our circumstances. 

However uncomfortable and awkward these circumstances are, I am choosing to make the most of them. If this pandemic has taught me one thing, it’s that no one is promised tomorrow. I want to embrace these times we are living in and be able to tell my grandchildren one day about the memories that were created virtually. 

If this pandemic has taught me one thing, it’s that no one is promised tomorrow.

The fashionista that I am wants to celebrate the uniqueness of this season the best way that I know how—through what I wear. If “dress well, test well” has been scientifically proven, I see no reason why “dress well, celebrate well” can’t be true as well. 

What you choose to wear for those virtual holiday family gatherings can make all the difference. Here are some suggestions on what to wear to virtual gatherings this holiday season. 


Hats are a trend that I am loving at the moment. I am especially loving fiddler hats. Since virtual gatherings typically display the top part of the body, head accessories are a must. A hat is an easy way to make it look like you put more effort into the outfit than you actually did. You could be wearing a cute sweater and a wide brim felt hat with pajamas bottoms and no one would know. The hat would get all the attention, and you will look trendy and stylish.


Speaking of head accessories, headbands are another option. I am a fan of chunky statement headbands, similar to what Kate Middleton is famous for. Pair a headband with a simple dress and you will look ready for any virtual gathering. 


Scarves make me think of winter and the holidays. They feel like a blanket around your neck, making anyone feel so cozy. This season, I am obsessed with bright colored scarves. Throw a lime green or fuschia pink scarf over any neutral outfit.

My favorite way to wear my scarves is just to drape it over my neck. I don’t do the fancy twists and ties, but feel free to experiment and try new things.


Layers are my favorite! My go-to outfit at the moment is layering a sweater vest or a sweater over a plain white Oxford. It is so preppy chic!

If you have a favorite holiday sweater, then throw it over an Oxford to switch things up. Add some accessories mentioned above. Layering really can’t go wrong, just try not to mix too many colors. I recommend layering neutrals and maybe one pop of color. 


My last recommendation for virtual gatherings are festive earrings. Earrings can help you achieve any look. If you want to feel classy, then throw on a pair of pearls. If you want to feel sleek, then wear gold hoops. If you want to be really festive, then DIY a pair of earrings.

Most craft stores sell basic earring hooks. Add some pom poms to the hooks or even small ornaments and you will have yourself a statement accessory and a great conversation starter. 

What are you planning on wearing to your virtual holiday gatherings? Leave more suggestions in the comments below. 

Image via Angi Welsch, Darling Issue No. 7

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