A holiday season outfit brainstorming journey

Avec moi

Quick reminder to fill out my survey about what you obsessed over this year, if you have a few minutes. I’ve had sooo much fun reading through the answers that have been submitted so far. I can’t wait to share them.

---

The month of December is really the only stretch of winter when I actually enjoy thinking about what to wear. Come the New Year, I know I’ll confront the impossible friction between staying warm and looking like myself, but not yet! December is sacred: there are other, more important motivations involved. Festive ones.

Doên cardigan (sold out in most sizes, but similar ones here and here) and SEA dress. Since the skirt is supposed to be kind of crinkly and textural, I haven’t found the synthetic fabric component to be an issue here personally (the upper portion of the dress is 100% wool). You could also create a very similar look with a tank like this (mind that it’s an extra 50% off with the code CHEERS) and a bubble-hemmed skirt like this, this, this, or this — all of which are made of natural fibers. My tights are these and they are THE ONLY TIGHTS I regularly wear. Fleece-lined forever!!! The shoes are Suzanne Rae, and the necklace is Dorsey.

For example, I’ve been fantasizing about pairing this red cashmere cardigan with this black, bubble-skirted mini dress — an outfit I’ve specifically envisioned in the company of poinsettias and pigs in a blanket. Now that holiday party season has arrived, I finally have the right occasion, which is thrilling.

The cool thing about an outfit that makes you excited to get dressed is how it can often unlock other, tangential outfit ideas when you pause to dissect what makes it sing. In this case, I was struck by the different possibilities of styling black with a punch of red. The combination felt notably festive, but not in a way that could seem too on-the-nose like, say, red and green, or black and gold might.

Same SEA dress, which you can see here in full glory. The pants are High Sport. I’ve now found two pairs (including the ones I’m wearing here) for under $375 secondhand, which I mention as a point of encouragement because I know they’re so expensive at retail. It takes patience to find them secondhand at a more reasonable price, but it IS possible. Here they are in purple in a size L for $375 👀. Or in red (long inseam version), size XS for $490. I also have these pants from J.Crew that are on sale for $86.50, and the fit is satisfyingly “crisp” much like the High Sport ones. Keep in mind the fabric of the J.Crew pants is heavier, so less appropriate for warmer months. Shoes are Suzanne Rae, necklace is vintage, and purse is Prada (lots of similar Prada nylon avail secondhand as well).

I experimented with swapping out the tights for my red pants and liked the resulting outfit just as much. (In my last Sticky Note, I wrote about how I’ve been hyper-fixating on the proportional harmony of a mini dress or tunic paired with kick-flare pants, so that was probably another contributing factor to my styling impulse here).

Doên top from a prior season but you can find it secondhand by searching for “Clarette Top” — see here, here, and here. Pants are Balenciaga which I found on Poshmark years ago thanks to some of my favorite secondhand holiday shopping keywords (crystal, rhinestone, gabardine, etc.) I paid $299 for them new-with-tags and they were originally $1,650, which feels less brag-worthy now that I’ve found them ON TRR FOR $275!!! If you’re a size M please buy. They really are the ultimate festive winter pants. My shoes are Dolce Vita, and my necklaces are from Athens Protasis, Renato Cipullo, and Arielle Ratner.

If the actual components of the outfit were festive in their own right, it seemed likely that the black/red juxtaposition wouldn’t have to work quite as hard. I tested this theory with crystal-studded pants and a ruffle-sleeved top, which indeed did more than enough heavy lifting for red to manifest as more of an accent than a punch in the overall look.

Same Doên top, vintage wool skirt, and heels from Twinset that are some of the only non-flat shoes in my closet. I’ve hung onto them because per question #6 in my closet clean-out guide they’re a key component of some of my go-to formal/festive occasion winter outfits. They’re also very extremely comfortable, and look exactly like the Prada bicolor sandals for a true fraction of the price.

Illustrated again here with the same top, plus a skirt and velvet platform heels.

Wearing a Piazza Sempione blazer that I got on TRR. The pants are Silk Laundry and they are a winter eveningwear staple for me. The bow is from Etsy — here’s a similar one. Same necklaces and shoes as above.

And again with silky pants and a coordinating velvet blazer and bow.

Reformation cardigan, Doên T-shirt (also love this one), same Balenciaga pants as above, and Ann Mashburn flats (also found these here on Poshmark).

When something relatively evergreen serves as inspiration (in this case, a color combo), it leaves more room for the interpretation of festive dressing to be less literal, and therefore more versatile. The last stop on this journey brought me back to the crystal-studded pants, this time more casually styled with a plain red T-shirt, black cardigan, and leopard ballet flats — an outfit I’d just as soon wear out to work meeting in the middle of February as I would to Christmas Eve dinner with my in-laws.

If you’re harboring any particular holiday outfit ideas or fantasies this month, I hope you’ll give us the rundown below.

xo Harling