How to Dress Comfortably and Still Look Chic at a Holiday Party

Hensley Metallic Long Sleeve Tunic, $1,295,
Courtesy Hensley
Galvan Lace-Trimmed Velvet Slip Dress, $2,495,
Courtesy Moda Operandi
Tosia Eden Dress, $825,
Courtesy Plan de Ville
Maggie Marilyn Silk Somewhere Striped Satin Shirtdress w/ Ruffled Frills, $960 and Maggie Marilyn Silk Somewhere Striped Drawstring Pants, $515,
Courtesy Maggie Marilyn
Markarian Grace Dress, $1,795,
Courtesy Markarian
Paper London Satin Jumpsuit, $392,
Courtesy The Outnet
Stella McCartney Rosie Silk Jumpsuit, $2,565,
Courtesy 24 Sèvres
Magda Butrym Sevilla Dress, $1,997,
Courtesy FWRD
Zimmermann Folly Kimono Dress, $850,
Courtesy Zimmermann
Alessandra Rich Printed Velvet Gown with Silk, $1,906,
Courtesy Stylebop
Cinq à Sept Serra Jacket, $495 and Alyssum Trouser, $395,
Courtesy Cinq à Sept
Johanna Ortiz Striped Button-Front Dress, $1,150,
Courtesy Saks Fifth Avenue
Raquel Allegra Cognac Velvet Drawstring Pant, $498,, Cognac Velvet Dolman Top, $450,
Courtesy Raquel Allegra
Sachin & Babi Taj Pant, $595,
Courtesy Sachin & Babi
Rebecca Taylor Violet Floral Satin Burnout & Velvet Dress, $595,
Courtesy Rebecca Taylor

It’s practically a fact that most holiday events are a minefield for uncomfortable situations. For example: being grilled by grandma about your dating life, keeping it cool while drinking eggnog alongside the CEO and running into that one-night stand under the mistletoe. Simply stated, we’re often invited to dress up and step out of our comfort zones a few too many times between Thanksgiving and New Year’s Eve.

So, why not dress in an outfit that’s the sartorial equivalent of a security blanket? We’re not talking about a sack made from fleece; there are a number of dresses, jumpsuits and pants that will at least guarantee your body feels comfortable in the midst of an awkward dinner party or festive cocktail hour. Luckily, the frocks of the season come with generous hemlines, forgiving silhouettes and are often delivered in the coziest fabric of all: velvet.

You can avoid showing too much leg, but still show off your personality in a zebra-print number from Alessandra Rich or dress in the most feminine tuxedo of all, with Cinq à Sept’s powder pink two-piece. We’re also partial to the very festive Johanna Ortiz shirt dress, that feels like a runway-ready candy cane. And if you really don’t want to change out of your PJs but you did RSVP yes, take a look at the Maggie Marilyn silk separates, that just might be the most stylish take on sleepwear we’ve ever laid eyes on.

Click through to see all 15 options for looking chic and feeling cozy throughout the holiday season.

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