One of the reasons I love dressing up is because it feels so…festive. Which is why, especially around the holidays, I find myself gravitating towards something with a bit of drama. And the dramatic piece I turn to (year after year) the piece I have the most fun wearing, the piece I actually find the most comfortable, too….is a giant princess skirt.

NOTE: This story originally ran in 2018, and has been updated for 2021. Not only am I still rocking this combo, but I’m clearly not the only one; there are now a bunch of these really fun skirts in stock. Looking for holiday outfit inspo for 2022? Run (don’t walk, sellout risk is real) to our holiday style page.

Classic Holiday Outfit Idea: A Fancy, Sweeping Maxi Skirt

I’ve styled up giant skirts in years past. In fact, the mint green tulle skirt featured is the one that started my obsession (and that old article has some solid styling tips), and I’m still wearing ShopBURU’s dramatic tiered skirt (first featured last year).

But the one dramatic skirt that should not be overlooked (among the layers of tulle, shimmery metallics and silky prints) is a sweeping black princess skirt. Unlike a black pencil skirt, this one is never boring. It elevates almost any top (silk cami, cashmere sweater, even a t-shirt) into something party-ready.

similar cami | similar skirt | similar boots | earrings

And let’s all recall the true genius of the giant princess skirt: it’s WARM. You can layer tights underneath, boots, legwarmers, snowpants — nobody knows. It’s the skirt of secrets.

similar cami | similar skirt | earrings

The day we shot this outfit, I paired my giant skirt with tall statement boots because if there’s one thing a princess skirt wants out of life, it’s blue snakeskin boots. (Or maybe just a reminder not to take yourself TOO seriously.)

on Me: similar cami | similar skirt | similar boots | earrings

On My Mom:  similar top | sequin leggings

On My Sister: similar dress

On the Guys (big and little): Our husbands are wearing Bonobos (more pics here), and the little guys are wearing Appaman.

Shop Dramatic, Ball-Gown Maxi Skirts

These skirts are all-out drama: full-length maxi skirts, done in some sort of fancy fabric (tulle, silk, etc.,). The advantage to these skirts (in addition to feeling like a princess) is that you can layer tights, leggings, tall boots, OTK boots — anything — underneath. It’s hard to not feel amazing (and comfortable) in a skirt like this.

Wear with: fleece tights (try Nordstrom brand or Plush), or semi-sheer tights (try Falke) and any sort of tall or OTK boot for maximum warmth.

Shop Holiday Midi Skirts

If you don’t want the length, there are plenty of statement-making midis. They have the drama of the maxi skirt, but are, admittedly, a little easier to walk around in.

Wear with: Bare legs and these sock booties (comfy even without socks). Too cold? Add these socks or Falke’s sheer tights. Obviously, tall boots (or OTK) boots can be worn for max warmth.

xo,
S