What To Wear Caroling (or, How To Be Really Warm, Stylishly)

I love everything about the holidays…the smell of a lit fire warming a family’s hearth, the sight of brilliant and colorful lights lining neighborhood streets, and of course hearing and singing traditional holiday songs.  Yes, you may call me a dweeb. If you ask me to go door to door to sing holiday carols, I will.  I even join in local caroling sing-a-longs all by myself…yes, I embarrass my family.

It all started back in fifth grade. As part of the “neglected” generation of the mid-70s, a group of my friends and I decided to carol house to house. No parents joined us, nor did we think two seconds about it. We started caroling at a friend’s house, whose mother invited us in for hot cocoa and homemade cookies. I was in heaven, mainly because it was the first time I ever came in contact with a peanut butter blossom cookie…you know the one…the deliciousness of a peanut butter cookie topped with a Hersey Kiss!

For all I know it was an 80-degree California day and we were caroling barefoot. However, it is much too cold here! As an adult, it is all about keeping stylish, cozy, and warm!


No other color says holiday like red! Also, I actually view red as a neutral because it pairs well with many different colors. This red vest is down filled and covers your ass-ets…there is no better bun warmer! Wear a warm knit dress and tall boots to complete a stylish winter outfit.


Need to be a bit more on trend in your winter wear? Add velvet! If you are not enthralled with the idea of an entire velvet ensemble, simply add a touch. A terrific example is this top by Johnny Was. It sports velvet at the hemline and sleeves, plus has an intricate, embroidered design to lend a Bohemian flair. You can pair it with our red vest or go for black…both work! Add a scarf, hat, and mittens should you need extra warmth and protection from the night chill.


One of my favorite looks is winter white. It is crisp, clean, and sophisticated. Plus, it pairs well, if not perfectly, with many different colors. The silky and form-fitting ribbed knit turtleneck pairs effortlessly with this poncho/jacket combo, a chic departure from a traditionally styled coat.

Caroling or not, there are multiple ways to stay comfy, stylish, and warm as this winter holiday season!


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