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.