November 2020

Holiday dressing:
3 comfortable, festive outfits by stylist Conni Jespersen

Conni Jespersen is a personal wardrobe stylist based in San Diego. Conni teaches online style courses, offers virtual styling, and encourages women to build a thoughtful wardrobe based on wearable, versatile pieces for an everyday lifestyle. You can find Conni at and on Instagram at @artinthefind and her style classes at

This holiday, the trend is all about wearing outfits that feel comfortable with a little bit of festivity thrown in. Here are three holiday looks that are both festive and comfortable for the winter season.


Nothing says holiday more than velvet. That’s what makes this velvet blazer in a deep gold hue a comfortable yet put-together piece for celebrating at home. I paired it with a simple silk camisole, jeans, and a printed loafer to complete the look. Even if you’re venturing out to a small family gathering, this outfit works for day or evening. The blazer is relaxed with a hint of a structure. It also looks great with a pair of wide-leg trousers or skinny jeans, or even faux-leather leggings. Dress it up or down.


If you want to put together a simple, chic outfit for the holidays, monochromatic is the way to go. Keeping it simple with an effortless color combination takes little guesswork and makes a stylish impact. This recycled-cashmere sweater is slightly cropped with a dropped shoulder and subtle puffed sleeves.  It’s both beautiful and comfortable. Pair it with cropped wide-leg cords and a pair of spotted loafers. Add a pop of pattern to the outfit with the shoe or the sweater. This sweater comes in a few different colors as do the cords. This monochromatic outfit is an ideal look for a holiday brunch or festive afternoon lunch.


If dressing up is more your style, but the holidays are going to be a little more low-key this year, pulling together something a bit fancier might be as simple as throwing on a little block heel and a festive sequined duster. This cardigan is purposefully oversized, making it even more cozy. Pull the outfit together with a chic pair of white cords and silk cami. I love the way this block-heel shoe balances fun and function, making it an ideal option for this holiday outfit.

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