I Get Stressed By Holiday Dressing—These 5 Fun Outfits Have Made It Easy

It’s the time of year where there just seems to be more than 101 events you have to go to: a catch up with old friends who are in town for the weekend, last-minute dinner parties, holiday movie marathons. I find myself putting pressure on myself to be dressed for each and every one. I suspect you might feel the same way.

So, in the interest of spreading the holiday outfit inspiration, I styled five looks for extremely specific occasions—you might not have these exact events on your calendar, and you don't have to dress exactly like me, but I hope these get the fashion wheels turning and empower you to look at your closet a little differently. And, for goodness sake, WEAR YOUR FANCY CLOTHES. A random Tuesday is a great day for sequin pants. Just saying.

For tobogganing, movie marathons, or any activity I’d file under “Cool Aunt/Uncle”

You're hanging out with the small people in your life! Definitely not the time for a fussy outfit, but you always want the kids to know how cool you are. (Just me?) Outfit requirements here: comfort, warmth, fun.

I think a great coat is always a must in the Northern Hemisphere—how else do we make it from November to April? (Mine's from Sittingsuits.) Personally, I scour eBay for quilted pants because they feel like a very silly updated version of sweats. You could do knit or French terry pants. Then, grab your coziest sweater for maximum snuggles and easy shoes for running around.

For being a plus-one

This is for those "I need to look presentable but I don’t know how dressed up people will be at this thing” events. I feel a suit with a shirt untucked, fun but sensible shoes, and a conversation starting-tie (mine’s a silk vintage Tamagotchi find!) mean you won’t fade completely to the background. Additionally, you can let your date shine!

This would work for dinner with extended family you haven’t met, a friend needing a date to work thing, or just a last-minute invite that requires dressing up. Variations of this look are a nice pant and a great sweater, or a go-to medium fancy-ish dress.

For seeing old friends—or when you need to look both cool and hot

You know the text: “I’m in town for a couple days—lets get a drink!” You want to look great, obviously, but you don’t want it to look like you were trying extra hard. Maybe this is a me problem? I get in my head when I haven’t seen folks for a long time. Perhaps it’s because I work in fashion, I feel there's an expectation for me to turn up in a look, but I don’t want to stunt too hard at brunch.

Pick up that dress that’s a little flirty, pair it with a cool, casual jacket and flat boots, and you're set. I’d also wear a design-forward button-down (think Nena Hansen and the like) with great barrel or loose-fit jeans to this outing.

For when you know you'll be eating a big-ass meal

Depending on your role, this might be the outfit you show up in to Friendsgiving or a holiday dinner, since you already made the cranberry sauce last night. Or maybe it’s what you swap into once you know the turkey is just about ready. You need to think about comfort again, but you also want to look cute and take pictures. Who doesn’t love holiday photos where you ate great food, had great company, and felt gorgeous?

No hard pants! Nothing too precious! Yes to layers for watching a Hallmark movie after dinner (or having a music video watch party). This one I’ll leave up to you to interpret, but what I focused on was: pretty, comfortable, easy but visually exciting. Shout-out to early '90s-inspired lace dresses and adjustable belts—oh, and a bag big enough to tote some leftovers.

For general fancy revelry

Maybe my favorite of the bunch: an outfit for when you just want to get dressed up. We all have varied definitions of what that might be—maybe it’s wearing a shirt that actually has a collar, maybe it’s a full gown, maybe it’s a faux-fur jacket and some sparkly pants. Whatever you pick up here, the point is to have a MF-ing good time. (BTW, my dress is from Elsom.)