A Stylist’s Rules for Feeling Like Yourself at a Holiday Party
What to wear and how to style it when you want to feel festive and like yourself.
The holidays can bring out the strangest expectations around how we “should” look — shinier, tighter, glossier, and somehow more perfected than the people we’ve been the rest of the year.
And especially in motherhood, there’s this added layer: I love being an active participant in making the holiday magic. There’s something about it that drops me right into the delight of the season. (But if this isn’t your thing, do not stress — I promise you’re nailing another area of parenting I’m absolutely below average at. No one is meant to be good at all of it. That’s a myth invented by Pinterest and patriarchy.)
But the whole month can start to feel like a mad dash of sparkle, unrealistic expectations, and an event, school program, party or dinner every single night. It’s like December asks us to become hyper-optimized, overextended versions of ourselves — and for some reason, we just go with it, even though we’ve spent the other eleven months building a way of being that feels grounded and real.
So when it comes to holiday event dressing, it’s easy to assume we need to “elevate” by transforming — or, honestly, abandoning — our actual style. But in my experience, the outfits I love most, the ones where I feel present and connected, are always the ones that feel like me, just… lifted a little. Illuminated. Not transformed. Not disguised.
Somewhere along the way, we were sold this Cinderella-esque idea of event dressing — the big “wow” moment, the dramatic reveal, the fantasy of showing up as a noticeably different version of yourself. But here’s the thing: looking unrecognizable isn’t the goal. When you stray too far from your own aesthetic, it stops feeling like style and starts feeling like costume. And it disconnects you from the very body and life you’re actually trying to celebrate.
Holiday dressing, at its best, isn’t about spectacle.
It’s about coherence.
Texture.
Ease and play.
Curiosity.
Point of view.
And showing up as the version of you that feels the most true — even in a sequined room.
Below are the principles I’ve found myself leaning on after years of styling — the ones that help me stay anchored in who I am during the holiday stretch. Take what serves you, skip what doesn’t. My hope is simply that something here gives you a little more ease, a little more room to breathe (metaphorically and literally), and helps you feel a bit more like yourself in the middle of all the December swirl.
1. Start with your real aesthetic — the holiday version is just a zhuzh.
December has a way of nudging us out of our natural style lanes. Play, yes — absolutely — but if you’re a color person, you don’t need to betray yourself by slipping into the obligatory LBD. If you’re a neutrals person, stay in that palette and let texture do the festive work. If your style is ease-forward, don’t abandon that in the name of “dressing up” — begin with ease and build from there.
Holiday dressing isn’t a makeover; it’s continuity with a little extra glow.
It’s taking the threads that already make you you and letting them shimmer slightly.
Think of the holiday version of your style as an echo — familiar, recognizable, just resonating at a slightly higher frequency.
2. Build your look with a three-part balance: sharp + easy + refined.
One of the simplest ways to make an outfit feel intentional (without slipping into costume territory) is to balance your look across three qualities:
sharp, easy, and refined.
You don’t need all three maxed out at once — in fact, that’s where things start to look overly done. You just need to make sure each shows up somewhere in the overall picture. It’s less of a formula and more of a feeling: the harmony between structure, softness, and polish.
Here’s what it can look like:
Dramatic dress (sharp) + undone, air-dried hair (easy) + soft, feminine makeup (refined)
Sleek bun (refined) + architectural earrings (sharp) + flowy, forgiving dress (easy)
Minimal outfit (easy) + bold, sculptural shoe (sharp) + clean, glowing skin (refined)
It doesn’t matter where each element goes — hair, makeup, clothing, accessories — as long as you’re mixing the three. That’s what keeps a holiday look feeling like you: grounded, dimensional, and not trying too hard in any one direction.
When everything is polished, nothing stands out.
A little imbalance is what makes you look interesting.
My friend Chelsey — whose makeup advice and industry experience I trust (and who just wrote a great explainer on holiday event make up) — said something this week I haven’t stopped thinking about: “If everything is highlighted, nothing is.”
It applies perfectly here.
Let one thing be sharp, one thing be easy, one thing be refined.
That’s the sweet spot
3. Create tension — that’s where your point of view lives.
My favorite outfits always have friction in them. A suede jacket over something formally “correct.” A slip skirt with a wool turtleneck. Sculptural wedges under an otherwise simple dress. A beaded or velvet bag with denim. The wrong-ish shoe that ends up being exactly right.
Tension is what keeps a look from feeling overly decorated or overly deliberate. It’s the difference between “I got dressed” and “this is my style.” It makes an outfit interesting.
If you’re ever unsure, ask yourself:
Where is the contrast?
Color, texture, proportion, formality — something needs to push against something else. A look with no contrast feels flat, like a showroom mannequin.
Contrast is what gives it soul and depth.
4. Let your hair create the tension your whole look needs.
Your hair is such an easy place to create balance in your overall look.
If you’re wearing something elevated — a dress with structure, shine or drama — undone, air-dried hair keeps everything grounded. It softens the edges and makes the whole thing feel lived-in instead of “big night out.”
If your outfit is leaning more minimal or textural, or the dress has a lot of flow and movement, give yourself some visual lift with a clean bun that follows your jawline. And by that, I mean: let the bun sit where your jawline would naturally extend. I discovered this by accident and it was honestly the difference between looking like myself and looking like a founding father. I would evangelize this tip to anyone with a head.
If your outfit is already edgy, that’s when you can let your hair have some volume or bounce. A sleek bun or super straight here would make everything feel too sharp — like you’re auditioning for a role you didn’t mean to sign up for.
My version of celebration is hair that feels a little undone or intentionally pulled back — never fussy, never complicated.
A “big” dress wants undone hair.
A soft dress wants structure.
Polished hair + polished outfit almost always reads costume.
It’s the tension that makes it feel like you.
I’m just going to keep saying tension again and again, okay?
5. Comfort is not anti-glamour.
I can’t be present if I’m constantly adjusting or tugging or trying to hide a bra strap that’s plotting against me. I tried on my contouring SKIMS before an event recently and decided, right then, that those are now a thing of the past for me.
Beyond the full-contact sport of getting them on and off all night, I’m just not into the idea of contorting my body into a sensory torture chamber for a night that’s supposed to be about being with people I love or celebrating something good or showing up in a way that feels connected.
And as a stylist, I genuinely understand shapewear has its place.
But for holiday gatherings — where I’m hugging people, eating real food, laughing, refilling my wine glass, standing for long stretches, bending down to talk to kids — it’s just not worth it for me anymore.
Holiday events are warm, social, chaotic and full of movement: chatting in circles, taking photos, helping in the kitchen, sitting on someone’s too-soft couch in a dress that doesn’t want you to bend. You’re talking to old friends, meeting new people, trying to hold a conversation in a room that’s way too loud and balancing a plate of appetizers you actually want to enjoy.
Comfort shouldn’t come last — it’s self-regulation.
It’s how you stay in your body instead of hovering outside of it, analyzing how you look to some imaginary peanut gallery. Or worse, literally trapped in shapewear.
Your sensory “yes list” should guide you as much as the dress code.
If a fabric or shoe makes you brace, it’s a no.
If something causes you to think about your outfit more than your actual night, it’s a no.
To me, no level of “pulled together” is worth being pulled out of the moment anymore.
6. Rent for the plot — not to erase your wardrobe.
There was a season where I rented clothing monthly, thinking I was expanding my style. I actually ended up feeling like I was wearing a series of costumes — nothing lived in, nothing familiar, nothing mine.
Now I rent for plot points only: the specific wedding, the gala, the one glittery dinner.
For everything else, I ask how to elevate what I already own or what I can buy with range and longevity.
7. Rewear, but let the styling evolve.
The real creativity doesn’t happen when you buy the piece — it happens every time you reach for it again. Choosing the dress or the top is just the base layer; the fun is in how you style it differently each time.
One piece can have five completely different lives if you let curiosity lead:
• a cropped jacket one night
• a turtleneck layered underneath
• an oversized blazer
• slingback pumps
• flats with an anklet
• a leather jacket thrown over a slip
Rewearing isn’t boring — it’s actually where your taste sharpens.
It’s the practice of seeing the same item through new eyes, letting it stretch and shift with you, and noticing what details make you feel most like yourself each time you put it on. It’s not repetition — it’s refinement
8. Materials matter more than sparkle.
Sequins can be great, but they’re not the only way to signal “holiday.”
Delicate lace, calf hair, feather trim, draped silk, matte satin, velvet, sheer chiffon — these are just as festive and often more sophisticated. They’re also usually more comfortable for sensory systems.
9. Let your coat be part of the look, not an afterthought.
Holiday parties are coat-forward occasions. Most people will see your outerwear before they see anything else, which means the coat matters just as much as whatever sparkles underneath it.
I walked into a gala the other night with my suede bomber thrown over my sparkly Hervé Léger, and at the end of the night — standing in line at coat check — mine was the only worn-in brown jacket in a sea of dark wools and glossy silks. An earlier version of me would’ve worried it wasn’t “appropriate,” but I actually felt the most like myself in that moment. It was stylish, it was true, and it grounded the rest of the look in a way nothing new could have.
A vintage oversized wool coat over a formal dress? Yes.
An old leather jacket over something delicate? Even better.
A great winter coat says, This is still me — even at a party.
It becomes the anchor — the first impression and the last
10. Add a detail with meaning.
I always think an outfit feels more alive when there’s at least one piece with a story — your flea-market purse, estate-sale earrings, your grandmother’s ring, the belt you found on a trip, the thing you’ve had for a decade and never stopped reaching for.
If you bought an entire look off a mannequin, it might be “correct,” but it wouldn’t be interesting. It wouldn’t have any layers. No history. Nothing to catch the eye or the heart.
Style works the same way a home does: it becomes richer when it’s built over time, not all at once. When the details come from different eras of your life, different seasons, different conversations. When they weren’t all purchased on the same afternoon or under the same fluorescent light.
Meaning adds dimension.
11. Let texture do the heavy lifting, not reinvention.
Texture is the easiest way to feel festive without abandoning your personal style. It adds dimension without demanding a whole new persona for the night.
Think draped silk, puddled velvet, gathered satin, lace that breathes or sheer panels that catch candlelight when you move. Even pairing a chunky sweater with a slinky skirt shifts the whole mood — suddenly it feels intentional and celebratory without being literal.
You don’t need a personality transplant.
What you need is texture, movement, depth — layers that let the light bounce a little.
12. Use silhouette to guide your confidence.
The “Big / Slim / Skin” rule from the Creative Pragmatist is truly undefeated. It’s one of those principles that just… works. Not because it’s trendy, but because it creates balance — and balance is what makes an outfit feel grounded instead of like it’s wearing you.
For me, it’s this simple: mix something big with something slim, and show just a touch of skin so the whole look can breathe — a rolled-up sleeve, an open neckline, a bit of ankle. Anything that leans too hard in one direction can start to feel flat, a little costume-y, or like it’s missing your point of view.
So if you’re showing skin, ground it with structure or length.
If you’re oversized up top, let the bottom be sleeker or sheer.
If the bottom is slim or slinky, add weight or volume somewhere else.
The architecture of your outfit is what helps your presence land.
It keeps the look intentional and balanced
13. Reinvent what’s already been done before buying anything new.
A couple of years ago, I grabbed the safety scissors from my kid’s backpack and cut the lining out of a pair of decade-old J.Crew lace pants. Suddenly they were sheer, a little strange, somehow modern — alive again.
That moment reminded me that holiday dressing doesn’t require newness; it invites creativity. Most pieces have a second (or third, or fifth) life in them if you’re willing to experiment a little.
Reimagine. Alter. Adjust. Layer.
Sometimes the most interesting outfits come from small tweaks — not new purchases.
I love looking at old event photos, archived runway shows, or vintage styling for inspiration too. Someone, at some point, decided opera gloves could make a comeback (and honestly, they’re such a smart way to change up something you’ve already worn).
Holiday dressing doesn’t ask for more things.
It asks for more play.
14. Choose pieces with life beyond December.
This is the part most people forget. If you’re buying something new, ask yourself: Will this still make sense in January? March? Next year?
The holiday season tricks us into thinking we need “special occasion” pieces — but the truth is, the best festive items are the ones that can slip right back into your everyday wardrobe once the lights come down.
Think:
• satin wedges
• a beaded bag or shiny tassel bucket bag
• velvet or feathered touches
• a great slip skirt (this one is $35 at J. Crew)
• a satin blouse you’ll wear to work just as easily
• a textured clutch or sculptural earring
All festive. All rewearable. All with range.
You don’t need holiday clothes. You need dimensional pieces that happen to shine under twinkle lights — items that feel like your real style, just shown through a slightly more luminous lens. Those are the things that earn their keep well past December.
15. Holiday dressing is a creative practice — not a performance.
Getting dressed is how I stay connected to myself: a tiny act of curiosity and intention that says, “I know who I am, and I’m bringing her with me.”
Holiday outfits don’t ask you to be someone else.
They ask you to show up as yourself — perhaps with a little shimmer, a little contrast, a little heart.
The goal is not transformation.
The goal is recognition.
A truer version of you, in a room that feels a little brighter because you walked in.
There’s a kind of glimmer that has nothing to do with sequins or shine — it’s the feeling of being coherent with yourself. Of slipping into an outfit and realizing, oh, this feels like me. It’s being comfortable in your skin, present in the moment, able to actually enjoy the night instead of managing it.
And you don’t need to be older, wiser, or more seasoned to access that feeling. You just have to be willing to:
• notice what genuinely delights you
• trust your sensory yeses and nos
• dress from curiosity instead of caution
• let your point of view lead
• choose pieces with a story over pieces meant to impress
• keep yourself recognizable to… yourself
If you were into this, tap the heart or pass it along. And if you’re craving more of this kind of content, you’re invited to join me as a free or paid subscriber — but truly, I’m grateful you’re here.
Jessica
Well if this isn’t just CHOCK FULL of gems!
EXACTLY what I needed to hear before a party I’ve been struggling to know what to wear to THIS Friday!