I Cracked the Code to Holiday Dressing With These Chic Outfit Formulas

Holiday dressing in New York requires strategy. Between the weather swings, the marathon of evening stops, and the many hats we wear at once, getting dressed can quickly become its own puzzle. How do you feel polished yet comfortable? Festive yet appropriate across a dozen dress codes in a single night?

From air-conditioned set days to warm dinners—and the constellation of holiday parties in between—these are the outfit formulas I return to repeatedly because they make getting dressed feel effortless, elegant, and enjoyable.

The Striking Capes

Part romance, part armor, a cape brings just enough drama to make a cold December night feel cinematic. It’s a layer you can keep on from the first stop to the last. I often pin a brooch or drape a shawl over the neckline for extra flourish. Wearing one instantly transports me into a softer, more romantic era, and occasionally, that borrowed fantasy is the motivation I need to leave my house during the winter season.

Here, I layered a leopard-print cape over a Naked Cashmere turtleneck, and slipped into a pair of sheer black tights and knee-high boots. As for accessories, I opted for my large DeMellier suede tote, which can easily cosplay as a laptop bag for office days and post-work dinners. Complete with an “Olsen Tuck,” this outfit gives off an effortless appeal.

While the cape pictured above is vintage, Colleen Allen makes an alternative that’s just as good. Fastened with a retro brooch—and styled alongside a velvet hat, silk pants, and suede heels—it’s the perfect ensemble for a holiday party.

Whenever I need a look that’ll transition from meetings to date nights, I turn to this polished formula. Follow my lead and wear Alix of Bohemia’s Kensington Onyx cape over Gemsun’s Alise jumpsuit. Finish things off with Le Tanneur’s Emie clutch and The Row’s suede heels.

The Secret Pajamas

Over the last couple of years, I’ve been embracing what I like to call “secret pajama outfits” (i.e. sleepwear that’s polished and intentional). As you’ll find on my Substack, I’ve worn versions of “secret pajama outfits" for dinners, evenings out, and travel, and I’ve noticed that my most complimented outfits are usually the ones that make me feel most comfortable.

Try one of the effortless looks below, and you’ll feel completely at ease and totally put-together. Start with base layers in silk, cashmere, velvet, or jersey. Next, add accessories that frame and elevate the silhouette.

Don’t forget to complete your outfit with at least one vintage piece to personalize the look.

For an extra cozy feel, pull on WNU’s silk button-up and Leset’s satin pants. Elevate the look with cap-toe heels, shimmering pearl earrings, a Deco-inspired bag, and a beaded necklace.

I find a suit to be the ultimate “secret pajama” when done right. Here, I styled a velvet hat with a pearl hatpin, a Brooks Brothers shirt (men’s shirts typically have more pronounced collars and cuffs), a Me+Em tux blazer, and Leset satin pants. Then, I tied it all together with a brooch and two-tone shoes.

I created the foundation for this look with a fitted top, a navy skirt, and tights. I topped it off with a heavy silk coat, a Le Sundial necklace, and a Casa Ayllon pouch.

I recently wore this outfit during a night out, and I truly felt like I was getting away with something. I floated through the entire evening as if I were in a nightgown.

The Finishing Touches

As previously written in my “Opera House” story, the waist has become a place for ornaments this season. Whether it’s a cashmere scarf, a silk stole, or a cummerbund, these accessories are the finishing touches on my holiday outfits.

I recently wore my vintage YSL velvet coat as a dress and embellished it with a cummerbund to complete the silhouette (a styling trick I highly recommend trying with Kallmeyer’s Louis Duster). Prada boots and a Le Sundial tassel necklace pull the look together with ease.

Consider wearing this Gigi Burris velvet hat with an All Three Studio top and Ashlyn pants. A vintage Chanel necklace, a pair of polished heels, and a red Gemsun pareo tied at the waist will set the tone for this outfit.

Overall, this look channels the playful feel of Chanel’s recent runway show and the iconic elegance of Diana Vreeland.

I’ve been reminding myself to experiment more with colors and patterns this season in order to tap into my whimsical side. So, I chose this vibrant printed dress styled with a YSL sash, a drawstring pouch bag, and suede shoes. Since my Missoni dress is sold out, try this option from Mango below.

This snug look is basically a “secret pajama outfit.” Copy this exact formula with a Malina evening jacket, a pair of Ashlyn pants, a set of two-tone Manolos, and a silk cummerbund.

The Main-Character Coats

This is my go-to formula for cold days when my calendar is packed with errands, meetings, and evening plans. Here, the coat becomes the outfit, worn with something simple underneath should I need to unravel once indoors.

The key is choosing a coat that doesn’t easily pick up lint—a textured weave, a subtle pattern, or a forgiving colorway will help your coat of choice to remain pristine throughout the day.

I love adding a nice flair, whether I'm cinching a scarf to my shoulder with a brooch, threading a necklace through the buttonholes, or popping the collar high to guard against the wind. This approach never fails me; it looks polished, lasts for hours, and keeps the day moving with ease.

This House of Dagmar coat is further embellished with J.Crew’s cashmere wrap and a vintage Chanel necklace draped through the buttonholes. I finished the look with cap-toe shoes and black tights. It’s an outfit that’s warm and ideal for a day that moves quickly.

A timeless look comes to life with WNU’s trench coat, knee-high boots, and Jimmy Fairly sunglasses.

For a decorated evening outfit, style a faux fur coat with a cashmere wrap and shimmering brooches. Then, throw charming heels, sheer tights, and a navy skirt into the mix.

The Evening Jackets

Evening jackets are a vital part of my holiday wardrobe. I wear them year-round, of course, but December offers the perfect excuse to bring out their festive charm. They’re ideal for moments when you’d rather not assemble a full outfit. Simply throw one over a pair of tailored trousers, a skirt, or well-loved denim, and you’ll feel instantly pulled-together. Needless to say, an evening jacket is a worthwhile investment in every sense.

For a look that carries beautifully through an entire night, style a velvet evening jacket with Ashlyn’s Blaine pants, chic shoes, a LIÉ Studio bracelet, and a Casa Ayllon ring. I recently wore this to a family celebratory dinner and then straight to a meet-up with friends afterwards.

The starting point for this look was my grandmother’s vintage belt, which gave a Marina Moscone jacket an even more sculptural waistline. The crushed slip Tibi skirt and Manolo suede heels kept the silhouette long and streamlined.

I styled a structured Malina evening jacket with Ashlyn's Blaine pants and vintage two-tone Manolos. Adding a brooch and a printed bag brought a bit of whimsy to the look.

This may be contentious, but I find this Saint Art leather jacket dips its toe into the evening-jacket category. I dressed it up with draped necklaces worn as a belt, tailored trousers, and tights for extra warmth.