You don't need another LBD
15+ ways to remix what's already in your closet for holiday dressing
‘Tis the season, y’all. The gift guides are circulating, Mariah is defrosting right on schedule, and your calendar just went from zero to unhinged. Cue the “what do I even wear to this?” panic.
The good news? For most holiday gatherings — the friends’ parties, family dinners, that low-key work thing — you’ve already got what you need in your own closet.
The pieces you reach for constantly can absolutely work for holiday moments. They just need a fresh perspective. Case in point: I shopped my own closet for a Friendsgiving and a charity dinner last week. I felt fantastic rewearing the wide-leg trousers I’ve been living in and a pair of jeans I completely forgot about.
So before you panic-buy a sequined something you’ll wear exactly once, I played dress-up in my own closet to show you what’s possible.
Heads up: This one’s too long for email and might get cut off. Read on the app for the full thing.
Button-Up Shirt
I wore my favorite Chava shirt with wide-leg jeans and pointy sling-backs to a charity dinner last week. No one knew I was channeling Nicole Kidman at Chanel, but who cares, I felt awesome. The dress code was “smart casual” — my tuxedo shirt and wide-leg jeans nailed the smart part, the heels took it past casual. I saw everything from corporate attire to black dresses to the quintessential SF tech/finance bro uniform (puffer vest with company logo over a button down).
I wore the same shirt to my birthday dinner last year and really wanted to show you the exact outfit, but I forgot to take a pic and now I can’t find my stirrup leggings. So we’re repurposing this collage from last year’s holiday style guide, ok?
This shirt will most likely make another appearance this season with an old Zara sequin skirt at a holiday thing (TBD…maybe the symphony?) sometime in December.
Or… maybe with a pair of lace pants (another old Zara) I found buried in my dresser.
By the way, you don’t need to buy a tuxedo shirt — a classic white shirt, oxford, or whatever you already own works just as well. The whole point is there are a gazillion different ways to remix an oversized button down.
Relaxed Trousers
This is what I wore to Friendsgiving last weekend. I’ve actually worn some version of a soft-waist pant and sweater combo almost every Thanksgiving. We have a no-hard-pants rule (non-negotiable) on this particular holiday. Plus, it just works, you know? It’s easy, comfortable, and with the right accessories, you can make it dressy and festive.
I like to pair something slim up top with wide-leg trousers to balance proportions, but a relaxed sweater also works if you want full comfort mode.
If you want to feel extra festive while staying comfy, try ~fancy~ pajama bottoms like these from Sleeper and swap the matching top for a Fair Isle sweater.
Mid to Dark Wash Jeans
Jeans and a cute top for a casual holiday thing? Skip the extreme fading, raw hems, or distressing.
For the “cute top,” think silk shirts or camis, anything with texture or detail that feels more special than your everyday shirt. A fine knit like this silk-cashmere turtleneck works too. Lately I’ve been loving monochromatic navy as a softer alt to stark black.
You can also add texture and interest through layering instead of just a straightforward top. Try adding a slim-fit turtleneck or a lace bodysuit under a shirt. Tuck everything in to highlight your waist.
Or skip the shirt entirely and wear a blazer as your top! A boxy, cropped style balances out the wide-leg jeans. No need for a belt since the cropped silhouette hits right around the waist.
An oversized blazer works too — make sure your base layer is fitted (also it doesn’t have to be sheer!) to create some definition.
Oversized Sweater
I’m really pumped that my hair is long enough for an Olsen tuck, which is my favorite cold-weather styling move: tuck your hair into a chunky turtleneck, add some big ass earrings. One and done. Oh, and your slip dress doesn’t have to hibernate until summer. Layer an oversized knit over it and now it works for winter holiday dinners. Comfortable, chic, completely unfussy.
If you don’t have an oversized turtleneck, chances are you have an oversized v-neck. Layering is where holiday dressing gets fun. The slim turtleneck underneath adds warmth and texture without bulk, and the v-neck lets it breathe. The slip skirt with lace trim keeps the whole thing from skewing too casual.
A metallic mule instantly dresses up what could easily venture into lounge territory. Swap them for boots and this works for a daytime thing. Keep the heels and you’re good for dinner.
Little Black Dress
Let’s reimagine the LBD. You probably have a few hanging in your closet.
I hate to break it to you, but wearing a dress over pants is back — and it’s nothing like the Y2K celebrity red-carpet looks.
I’ve had this knit maxi from Staud for 5+ years and I’m glad I never got rid of it. Wearing it as a dress on its own feels kinda stuffy, but worn open over jeans gives you coverage and structure without feeling too formal. Only button it through the top of your jeans — you want the dress to drape open and show the denim underneath. Leave everything unbuttoned from the hips down and let it move when you walk. Now your old black dress feels fresh and intentional.
What I love about a simple slip dress is you can wear it like a skirt and no one knows it’s actually a dress. I love a two-for-one deal. A cool jacket instantly gives your black dress a makeover. The embroidered silk adds texture and feels dressy enough for a holiday party but not so formal you feel overdressed.
Another layering example to give your LBD a second life. Adding a slim turtleneck underneath makes it works for colder weather and feels more interesting than wearing the dress alone.
A bold turquoise and silver collar over the turtleneck instead of a statement earring also feels more unexpected. Turquoise might feel like a summer stone, but I’ve always loved wearing it year-round (it’s my birthstone). I mean, doesn’t turquoise and black in winter just scream chic?? It also works beautifully with red and khaki…
Small details = Big impact
Ok, so you’ve got the outfit figured out. But now you want to take it from “you look cute” to “wait, where did you get that??” You probably already own at least a few of these game-changers.
A vintage brooch on your blazer lapel, your coat collar, or even clustered on a simple sweater. Instant upgrade. The more ornate and slightly off-kilter, the better. Take some inspiration from the reigning queens of brooches on Substack: Giulia C. and Sierra Goodhue.
I found a couple vintage options from Etsy: Reinad Lily Rhinestone Brooch // Rhinestone Brooch // Pearl & Rhinestone Brooch // Art Deco Onyx Brooch
Full disclosure: I’m not an expert at sourcing vintage finds. May I suggest some of my favorite secondhand curators: Katie Casper, Glenn Mae, Kendall Flavin. They’ve got you covered.
Not vintage but this Talia Perla brooch has been on my wishlist for almost a year now. Also loving this vintage-inspired Marlies Grace brooch and dripping fern brooch from Rachel Comey.
CAPITAL F: F-U-N shoes. Your shoes can make or break an outfit. Period. This is not the time to play it safe with footwear. Rhinestones, studs, grommets, any texture or embellishment — all of it works. Metallics catch the light and automatically read as festive, even when everything else is basic. I wore silver mules in almost every look I showed you because they just go with everything!
Here are some fabulous options: Metallic Mules Under $150 // Embellished Mesh Flats // Silver Slingback Flats // Sculptural Wedge Sandals // Calfhair Kitten Pumps (runs small, take a full size up) // Embellished Slingbacks // My dream Dries Van Noten heels (sadly not in my size) // Another fabulous Dries heel
A silly little bag. Ditch your everyday tote and opt for something smaller, more special.
Check out these silly little bags from: Marlies Grace // Le Sundial // Lizzie Fortunato // Liffner // Staud // Chaan Luu // Rabanne // Dries Van Noten
Textured hosiery. Opaque black tights are fine, but try some texture — ribbed, sparkly, or patterned — to up the ante. You don’t need to spend $$$ to make a skirt or dress feel more interesting. This is my friend Tina Boetto’s style signature.
If you’re wearing ankle-length pants, try adding sheer textured socks with loafers, pumps, or strappy heels. That little detail peeking through feels intentional.
Statement jewelry. Something with presence. Sparkly earrings pull the focus upward and make even a simple outfit feel finished. A shiny tennis necklace on your collar. A bold cocktail ring catches the eye when you’re clinking glasses. A metallic cuff over your sleeve.
You also need to consider hair and neckline when wearing bolder jewelry. Generally, you don’t want a statement earring and a statement necklace competing for attention.
Statement earrings + high neck = hair up (unless you have short hair ofc), skip the necklace but you can wear a cuff
Statement earrings + open neckline = hair down, skip the necklace (or opt for a simple one)
Statement necklace + open neckline = hair down, keep the earrings minimal (a simple stud)
Statement necklace + high neck = hair up if long, hair down works if shoulder-length or shorter
Some statement pieces to consider: Dorsey Odette Earrings // Lie Studio Ruby Earrings // Le Sundial Opera Earrings // Chaan Luu Drift Earrings // Agmes Stella Earrings // Ben-Amu Cuff // Jullietta Onyx Necklace
Hair/neck/arm/waist adornments. It’s that little pop of personality that makes people think you really thought about your outfit (even if you threw it together in ten minutes.)
A few outfit finishers to consider: Jennifer Behr headband // Jennifer Behr barettes // Jennifer Behr velvet scrunchie// Toteme fringed velvet smoking scarf // Le Sundial tassel belt // Agnelle Lace Opera Gloves // TWP beaded topper (throw it over a white button-down) // Rachel Comey embellished bandana
But What About the Actually Fancy Stuff?
Everything above works for casual holiday moments. But some of you have real dress codes staring you down. “Cocktail attire.” “Black tie optional.” “Festive formal” (??). The work gala, the charity dinner, your partner’s company party — jeans and a nice top won’t cut it.
You can’t statement-earring your way into formal attire. These events have rules, and showing up underdressed sucks.
I just started offering styling sessions for this. We get on a call, decode what the dress code actually means, and figure out your plan. Sometimes you need to rent something. Sometimes you need to buy something specific. And sometimes — this happens more than you think — you already own it but didn’t know it would work.
Book a consult or a 1-hour virtual styling session.
If you’ve got multiple events (low-key and fancy), I’ll make you a Custom Holiday Lookbook instead — 4 or 8 complete outfits with the full breakdown. Which shoes, what jewelry, how to rewear the same dress three different ways. It saves you from panic-buying the day before.
Purchase a Lookbook
Formal events are trickier. The dress codes actually matter, and there’s less room to wing it. Figuring out how to meet those expectations while still feeling like yourself — that’s where I come in.
Read more about my styling services below.
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Nothing a perfect white button down cant do! And taking major outfit inspo from every look!
You've inspired me to pull out my turquoise necklace and try to style it for the winter !! Also, impeccable style and you make me want to get a pair of silver shoes.