I’ve read a lot of holiday style advice over the years, and most of it assumes you’re excited, well-rested, and attending events you actually want to be at. It assumes you’re looking forward to dressing up. That you have energy. That you’re feeling festive in a way that’s uncomplicated and photogenic.
It assumes December is a fun puzzle to solve with the right outfit.
For a lot of women, that’s not the month they’re having.
December is often the most compressed, emotionally crowded time of year. Work doesn’t slow down, it just pretends to. Social obligations stack up. Family dynamics resurface. The days are darker, the weather is worse, and the margin for discomfort suddenly shrinks.
And yet, the holiday fashion advice keeps coming:
Have fun with it.
Try something sparkly.
Just throw something on.
As if the problem is a lack of creativity.
What this advice rarely accounts for is how many invisible negotiations women are making when they get dressed this time of year.
You’re not just choosing clothes, you’re deciding how visible you want to be. How much energy you’re willing to expend and whether you want to signal change, continuity, success, ease, effort, or none of the above.
You’re also dressing for people who know you well. And for people who think they do. For rooms that carry history, sometimes more history than you’d like, and you’re dressing knowing there will be photos, and that you won’t get to control the angle, the lighting, or the story those images tell later.
That’s a lot to ask of a sweater.
When women tell me they’re suddenly overthinking what to wear in December, they often assume something is wrong with their wardrobe. That they need a “better” holiday outfit. Something special. Something new. Another thing to add to the pile of never ending responsibilities this time of year.
But more often, what’s changed isn’t finding the perfect outfit, it’s about tolerance.
Tolerance for tight shoes.
For scratchy fabrics.
For outfits that only work if the night goes exactly as planned.
For performing cheer when they’re tired.
For leaving the house at all when it’s cold, dark, and all you really want is to stay home under a fuzzy blanket with no expectations.
At this point in the year, many women don’t want to be more stylish.
They want to be more supported.
SO WHAT DOES “SUPPORTIVE” DRESSING ACTUALLY MEAN RIGHT NOW?
Supportive dressing in December isn’t about upgrading your wardrobe. It’s about reducing friction.
A few ways to do that — without turning getting dressed into another project:
1. WEAR WHAT ALREADY WORKS
If something has gotten you through long days before, trust it again. Unless you’re up to it, this is not the month to audition new silhouettes, new shoes, or new versions of yourself. Free up your bandwidth and prioritize what’s really important.
2. LOWER THE PERFORMANCE BAR
Not every outfit needs to feel festive, memorable, or “worth the effort.” Neutral, understated, and emotionally quiet is often the most honest choice this time of year.
3. DRESS FOR THE LONGEST PART OF THE DAY, NOT THE HIGHLIGHT
If the event is two hours but the day is twelve, choose clothes that support the full span. An outfit that only works for the moment tends to demand too much from you.
4. LET ONE THING DO THE WORK
One familiar piece you feel good in, a piece of jewelry, a shoe, a scarf, a top, can carry an otherwise simple outfit. Everything else can stay understated.
5. GIVE YOURSELF PERMISSION TO REPEAT
Repeating outfits is not a failure of creativity. It’s a sign you’ve found something that works under real conditions.
You don’t need a perfect holiday outfit.
You need clothes that let you stay present in the room instead of inside your head.
Sometimes the most honest holiday outfit is the one that lets you stay present instead of preoccupied, even if it wouldn’t make a great roundup post of covetable looks.
I don’t think holiday dressing is hard because women don’t know what to wear.
I think it’s hard because December asks us to show up in too many places at once, physically, emotionally, historically, and clothes are expected to quietly manage all of it.
If getting dressed feels more complicated than usual right now, that doesn’t mean you’re doing it wrong. This isn’t a style problem. It’s a December problem.
Wise words! I’ve struggled to put into words how challenging it is to dress for the many demands of the season. This post beautifully explains it.
Here’s today’s solution. I’m meeting a friend for lunch, then going to physical therapy with a tight break in-between, then doing a video call.
So, no red/green outfits and jewelry that’s seasonal but not clearly holiday.
My pants are blue jersey and my shoes are blue street sneakers for therapy that still works for lunch and lets me change out my pink cashmere top for a tee in a hurry. A pendant tassel necklace is glitzy and comes off and back on fast. Lipstick and eye makeup carry the load. Living out of town means I spend much time traveling and learned to mix and match my you’niforms for a wide variety of occasions. Who says velour pants can only be for parties?
Good thoughts, Bridgette!
Yep! Some sparkly jewelry and a bold lip and bam! You are now Holiday Ready!
I love this because YES. I have a Wonder Woman Christmas sweater for whimsy (drinks at the pop up Christmas Dive Bar), a burgundy sweatshirt dotted with rhinestones for comfy but still festive (worn to an open house/ to see the Christmas boat–under a jacket of course), and a 15 year old merino cardigan from Eddie freaking Bauer of all places, that has some heat stamped metallic geometric designs that have zero to do with the holidays but is just sparkly enough to work at the school holiday choir concert and to go see Post Modern Jukebox (props to the women there in art deco sequin dresses but it was raining sideways and I Could Not.) All worn with various washes of denim and my faux-fur lined Doc Martens. (OK, so no fancy company parties for me but I really don’t mind, and the holidays with the in-laws next week will likely feature weather in the 60s and very casual hangouts, so…) I love all the photos of sequin skirts Iscratchy and cold) and velvet heeled boots (everyone’s house is shoeless these days) and faux fur (too warm for inside, not waterproof enough for outside) but it’s all wishful fantasy nonsense for me. Where are you going in that, indeed.
Great post
This is one of the best holiday blogs I’ve ever read. Thanks for reminding us to slow down, be intentional, find joy (gladness + gratitude) in the small things.