Dressing for the holidays is supposed to be fun. It has words like “festive” and “cheer” in it, after all. But I know what it’s like to be a bit fraught, wondering what to wear so you stand out but fit in at the same time. There is a key nuance to the worry here, though, that most of us overlook: it’s actually about showing up at an event looking the opposite of everyone else, in tone and vibe (and that just sucks). I don’t want to just have my style look good…I love the satisfaction of knowing that I nailed it. Not the “look for the event” but interpreting my style perfectly for the event.

And to top it off, we’re Creative Pragmatists. So, the overarching goal is to show up, no matter the theme or locale, as ourselves. Because when we don’t, that’s when we feel most off. Not because we didn’t look great, but because we looked like someone else.

I’ve studied the many DM’s I’ve received about the places you’re headed to over the season and your thoughts about what’s got you stuck. I’ve separated them into groups, by general situation, key considerations, and the tools that will help you problem solve. You’ll see below that what to wear when little Noame is tapping her way across the stage bears the same consideration for what you’ll wear to meet your boyfriend’s family for the first time at a holiday dinner out. When you break situations down through this lens, you’ll see it’s not about age, geography, or other general demographics. It’s about having the right tool set in place that speaks to your personal style and applying a mindset to any situation that is at once creative and pragmatic. Ok?

Formality without the Formal

The Scene: These events require a certain amount of decorum. These are corporate holiday parties at venues with wood paneling and many people with three or more names. Think: lots of lawyers, martinis and jokes that require that you really hone up on that half-laugh. The vibe is formal in manner but not to be confused with true formal attire.

The Solution: Have tools on hand that allow you lean into a bit of irony and holiday creativity at the same time. The play on the banker’s shirt, the smoking tuxedo vibe, the classic but unstuffy pump and sheer hose all put you squarely in the right-clothes-in-the-right-place, but with proportions and interest fully on point. The over-the-top earring and the interesting skirt complete the vibe.

Sexy (not my word, theirs) Festive with Friends

The Scene: When color, glitter, and platforms, all at once, are on the roll call, but they’re not part of your vibe. This can be as simple as a holiday dinner and bar hopping with friends, but everyone’s committed to “getting dressed.” Your friends want you to cut loose and wear the plunge sequin dress, so you “stop hiding your body.” You’ve explained that your style is chill and modern; it’s not about hiding, it’s about reflecting an ease with yourself, and they still don’t get it. And that’s ok, we’re all different. You want to show up for the occasion but still feel like yourself.

The Solution: You’ve got those pieces in your closet that you live in. When you put them on, they’re inextricably you: the big but refined and tailored cutout sweatshirt or the tall crocodile boot, for example. These mainstays, mixed with true festive items, give you balance every time. The chic skirt, the bling on the ears or fishnet and silver sandals–the full look is clearly set for going out. Going out as you.

The True Holiday Spirit Event - At Home

The Scene: You’re celebrating at home with those closest to you, lighting the candles, sitting by the tree, enjoying treasured traditions. You want to be in the moment, but you’re also in your house and it should be cozy but holiday.

The Solution: Reach for items that read cozy, but don’t think that you’re headed to the couch for a binge of Curb Your Enthusiasm. Tools that work here are ones with tremendous ease but are still refined, materials that are soft but with structural interest, and a shoe that’s got shine but is just perfect for running around in the kitchen and enjoying time at the table with family. And always, always, a pair of earrings that indicate something special is happening, a really dressy layer that belies all the ease.

The True Holiday Spirit Event - Outside the Home

The Scene: These events hold a special place for you during the holidays–think the Nutcracker, your kid’s dance rehearsal, or any sentimental ceremony where you want to feel special. But it’s not an “all eyes on you event,” it’s about the moment, the celebration. It’s kind of like you’re dressing specially to honor the idea that going to the ballet or watching your kid on stage feeds the soul.

The Solution: Items that feel beautiful, warm, and easy all at the same time are the pieces I reach for: the draped dress with ruched sleeves or a rich sweater and a heavy satin skirt, paired with a hair clip that’s got holiday written all over it but isn’t screaming for you to look over my way. The boots are important here, ones that are functional but refined. I don’t look as if I’m headed for a hike, but they still manage to take things down just a notch.

Superman Events - the office party.

The Scene: Some events require a quick change-up, hence the Superman reference—get it? He had to change into his costume in a phone booth… Anyway, this is the office party. You’re going from desk to event and sometimes it feels as if your only choices are polarizing. You’re either an ornament ball at your desk all day, or the one at the pasta station who looks like you’re about run through a PowerPoint. The idea here is you want to feel right—at work and at the event—and not required to pick either or.

The Solution: Pieces that can be layered easily with a jacket during the day, like the silvery grey ruched top or black bustier here. What makes them easy for layering? They’re fitted to the body, or they’re sleeveless. And they’re a statement on their own and in full holiday vibe when paired with a glittery shoe and a fabulous earring. You can also lean into irony here: a sharp button down unbuttoned in a louche manner, paired with layers of necklaces, something sheer like this pair of socks, and a metallic sandal, giving festive spirit with a wink to the boardroom.

The Holiday Event - with a temperature twist.

The Scene: It’s Christmas Eve, New Years, or any festive get together, but you’ve got climate concerns outside of your norm to contend with. Super-hot locales confound many at this time of year. Watch any holiday movie, the host isn’t usually serving eggnog in flip flops.

The Solution: Pieces in your closet that nod in color and richness to the celebration at hand, but in weights that are versatile. Think slip skirts in a spirited red coupled with a knit that can be wrapped easily around the waist or put on or off as air conditioning or an evening wind dictates. A gold ballet slipper seems to be the key tool in the closet for this time of year_—you can see it working in myriad situations. Mixing in jewelry with freshwater pearls gives a subtle nod to your locale. A heavy silk dress in a deep green paired with a simple gold mule is undoubtably perfect for this need, almost as if the designer herself knew she’d be in Key West over the holidays (facts).

Holiday Meal at Home

The Scene: It’s the dinner where you’re not wanting to be dressed up…to an extent. It’s family and it’s about them and being in the moment and something feels incredibly awkward about heels in your kitchen or little Charlie being forced to wear a collar or tie at the table. But it’s a special night, a t-shirt or work out leggings just don’t cut it.

The Solution: Rich luxury like heavy cashmere that’s modern in proportion and can be dialed up with the addition of sparkles in the form of exaggerated diamond earrings and a watch that’s making a big statement while being discreet at the same time. Slippers top off the opulent shine of the pull-on satin pants or give a serious level up to the sculpted Calder in a polished sweatsuiting material.

So, here’s the takeaway: I’ll never be able to cover every permutation of an event that you’ll have in your life. But I have shown you how to think about events through the lens of critical thinking. Identifying what problem you’re really trying to solve (how do I meet the situation’s parameters but show up as myself?), determining what factors are most important (comfort, respect, high spirit), assessing what items you have or need, and identifying various solutions that can be mimicked in your closet or found in the real world. Especially at Tibi, but I’m clearly biased. Happy Holidays!