Cheryl Shops

I knew several months ago that, for the first time in my 42 years, I wouldn't be spending Christmas in Chicago with my mom. We had instead made plans to drive down to L.A., rent a house in Venice Beach, and have an outdoor, socially distant Christmas with Sean's family. But earlier this week, after realizing that restaurants are closed for outdoor dining, parks and beaches may be next, hospital ICUs are at capacity, and the governor's orders basically prevent interacting with anyone outside of your immediate household, we decided to postpone our trip to February or March. I had been looking forward to our trip for many reasons—a change of scenery, seeing friends and family, traveling somewheres, anywhere—and I'm surprised I'm not more upset about having to cancel it, but I know that it's the right thing to do, and that this is hopefully a one-time-only concession. This year has definitely had its share of disappointments, but I'm trying to look on the bright side. For one, we don't have to deal with jacked up travel expenses, crowded airports, novice travelers, awkward conversations with relatives who have opposing political viewpoints, and so on. For another, it's an opportunity to create our own new traditions. I'm thinking we'll order extravagant takeout from a local restaurant for Christmas Eve dinner, then open a nice bottle of wine and open presents. And as for what I'll be wearing, it will probably be much more low-key than my usual, but (hopefully) still somewhat festive. Here are some ideas, from dressiest to most casualest. 

Little black sweater dress

Oh man, I miss wearing this dress—it's one of my winter work go-tos. That said, it's really comfy and can accommodate a decent-sized food baby, should you be indulging in eggnog, a feast of seven fishes, or what have you. The boots are good in case you need to go outside, even in inclement weather. 

OUTFIT DETAILS: COS sweater dress (current season here) | Isabel Marant Chess boots  

A turtleneck and leather skirt

The leather skirt makes this outfit look much dressier than it actually is, and the oversized turtleneck keeps you nice and warm. Oh, and the boots are one of the comfiest pairs I own. 

OUTFIT DETAILS: Free People sweater (current season here) | very old Zara skirt (similar here) | Balenciaga city bag | Calla suede boots (c/o) (similar here) 

T-shirt and black slip skirt

This black slip skirt is a Cheryl Shops bestseller for 2020 (I own it in two colors), and even though I'm wearing it with a vintage-style tee and sneakers, the outfit still feels adequately dressy for California. 

Silk blouse and gray jeans 

We're getting into pretty casual territory here, although the silk blouse makes things feel a little dressier than a cotton shirt would. I would not advise wearing this to a big meal, however, if you're a sloppy eater like I am. 

OUTFIT DETAILS: Zara jacket (similar here) | Everlane shirt | Frame le high straight jeans | Golden Goose superstar sneakers 

A knit blazer and sweatpants 

This was one of my most popular outfit posts this year, and I definitely still wear it on the regular. The knit blazer makes it look slightly more dressy than it should be, but it's definitely all about comfort. 

OUTFIT DETAILS: J.Crew Sophie blazer | Free People scarf (current version here) | Rag & Bone striped tee (similar here) | Lou & Grey signaturesoft sweatpants (c/o) | Ugg boots (current version here) 

Just pajamas 

If you're not going anywhere, why bother changing out of your pajamas? This looks is from an Instagram collaboration I did with Cuddl Duds and while I was slightly embarrassed to be wearing it in public, I was comfy AF. 

OUTFIT DETAILS: Cuddl Duds stretch thermal top (c/o) | Cuddl Duds stretch thermal leggings (c/o) | Everlane cashmere beanie | Vans sk8-hi sneakers