3 Little Black Dress Outfits Perfect for the Holiday Season – Charm

If you know me, you know that I’m a huge fan of holiday dresses. I’m a self-described magpie, in that I’m drawn to anything with sparkle and shine, so I’m always looking for an excuse to shop for something fun and festive. But that doesn’t mean I’m always wanting to spend money on something new. Sometimes, the perfect look is something that you already have in your closet. You just have to style it a little differently.

As an influencer and editor, I have a lot of clothing, so I truly know a piece is special if it’s something I just keep coming back to. This mini slip dress from plus-size designer label Gia/IRL is one such piece.

Gia/IRL

Delilah Mini Dress

To me, this is the perfect little black dress. Gia Sinatra, the founder of the brand, wears plus sizes herself; she created Gia/IRL to make what was missing in her own wardrobe. That type of personal experience is really evident in the fantastic fit and cut of this dress: It highlights curves without clinging, flows over a belly without adding extra volume, and just looks hot on. It’s so good, I’m constantly finding new ways to style and wear it.

When I was thinking about how to navigate all the events I have on my calendar this season, I realized this very dress was at the core of a lot of my styling ideas. Ahead, I break down how I’ll be wearing my favorite LBD to all different types of holiday parties, from the cozy gathering to the big night out—and how you, too, can breathe new, festive life into your go-to dress.

For a Cozy Soirée

Sarah Chiwaya wearing a little black dress, cream cable knit sweater, and tall leather boots

Knee-high boots and mini skirts are having a real moment right now. I’ve always loved the juxtaposition of a short hemline and a chunky sweater, so I decided to combine all of those elements for my first look—perfect for a Friendsgiving get-together.

This cable-knit sweater from Abercrombie is from last year and almost sold out, but the brand has a similar version this season with a cute angled twist on the classic pattern. The slight a-line on the Gia/IRL dress makes it well-suited for layering as a skirt, and the mid-thigh length gives it a flirty vibe without feeling overly exposed. If you wanted to add a little more coverage, you could add fleece-lined tights that give the effect of a sheer black pair, but are much warmer.

For boots, I went with my go-to leather pair from Duo (I wasn’t kidding when I said these are on heavy rotation!), and finished the look with a whimsical rose bow hair clip from designer Samantha Pleet. (This exact version is sold out, but a similar style is still available!) The overall effect is cute, cozy, and a little coy—and I love it.

Abercrombie & Fitch

Textural Stitch Cable Crew Sweater

Duo Boots

Haltham Standard Shaft Knee-High Boots in Black Leather

Samantha Pleet

Persephone Clip

For a Fashion-Forward Party

Sarah Chiwaya wearing a little black dress, sequined skirt, and silver boots

If you want to go for a maximalist, more-is-more vibe, try some proportion play by adding sheer skirt underneath a mini. Sheer items have long been a layering go-to, but there’s something particularly fresh about adding a cool see-through layer under a short hemline instead of over it, especially if it’s in a contrasting texture. I’ve seen great IRL street style examples of this with oversized tees, boxy blazers, and mini skirts, so I was intrigued to try it with a short slip dress.

I already had this mesh paillette midi skirt from ASOS in my wardrobe when this notion first occurred to me, and the combination made perfect sense in my head. It felt so right that I almost got a little scared—like, would this be one of those horrid times where it was only a look in concept? But the moment I put it all together, I was thrilled to discover it works just as well in practice. The curvy, body skimming silhouette of the Gia/IRL mini dress is still visible, and the black and silver paillettes look like a natural match when peeking out from under.

Paired with my favorite structured bag, the Brandon Blackwood Kendrick Trunk, and true wide-calf silver boots from Dolce Vita, I was smitten.

ARRANGE

Curve Sheer Grid Sequin Maxi Skirt in Black

Dolce Vita

Ryatt Extra Wide Calf Boots Silver Distressed Leather

Brandon Blackwood

Kendrick Trunk

A Hot Night Out

Sarah Chiwaya wearing a little black dress with a sparkly clutch and gold jewelry

Part of the reason I love this particular LBD so much is because it can really stand on its own. Hell, I wore it for my birthday last year with nothing but platforms and vibes. It doesn’t need much in the way of styling to be a hot outfit. But the holidays always call for a little sparkle, in my opinion, so if you really want to let it shine on its own, the best way to do that is by amping up the accessories.

I’m a big fan of the molten metal trend that’s everywhere lately, and I think designer Alexis Bittar does it best. It has long been one of my favorite brands for statement jewelry, specifically its signature bangles and unique lucite earrings in amorphous, organic shapes. For this holiday night-out look, I went with all of the above, with a mixed metal stack of molten bangles in large and small on each arm, and a bonus cuff to keep it from being too symmetrical. Importantly, every bracelet comfortably fit over my hands and on my arms with ease (not always the case when it comes to designer jewelry as a plus-size shopper!)

To keep the mixed metal theme going, I finished the look with a gorgeous lace-up detail clutch from the brand in a shimmery fabric that shifts from silver to gold with the slightest motion.