What To Wear: A Stylist’s Guide To Holiday Dressing

Words by Keven Amfo

19 June 2020

During the year's busiest social season, full days give way to evenings with parties, inevitably meaning a bit of chaos when it comes to appropriately planning what to wear. In anticipation of the busy weeks ahead, we consult with celebrity and editorial stylist Kerri Scales on how to simplify the planning—whilst being comfortable and maximising the impact of your look.

Do I need to adhere to the recommended dress code?

Says Kerri, "Yes! Dress codes are set for a reason, and it's the host's way of saying, 'this is what we'd like you to wear'—aka, this is the vibe of our party. My rule of thumb: it is always better to be overdressed than under."

If we've been invited for 'cocktails'… what is a good option that's a bit outside the box (for men and women)?

For women, holiday party dressing is generally a great time to experiment with new silhouettes. "Instead of a cocktail dress, opt for something more menswear-inspired, such as satin-trimmed tuxedo pants paired with a silk blouse; or even a two—or three!—piece suit in a dreamy satin hue," recommends Kerri.

A bit of sparkle, such as a sequin skirt (cooly paired with a T-shirt and blazer, or with a chunky knit), or an ethereal tulle skirt (paired with an oversized button-down and a party heel), are two enduring favourites that can be reimagined based on their styling.

The holidays can be a time for men to experiment a bit more as well. According to Kerri, "Corduroy is back in a big way. Embrace something rich in texture and vibrancy—corduroy, velvet, plaid—adding a bit of novelty to the look. To make it more cocktail-appropriate, dress it down a bit with a good rollneck or cashmere crewneck jumper, dark denim bottoms, and a classic Chelsea boot." Take a look at our formal attire guide for men to get some further inspiration.

It's cold, and I don't believe in wearing fur. What are some other options?

"My go-to outerwear for cold but dressy occasions is a floor-dusting hour-glass waistcoat—timely and timeless," Kerri says. Alternatively, oversized outerwear cut from heritage fabrics, such as herringbone and plaid, are not only warm but also elegant.

Is there anything that truly transitions from office to dinner to party?

"For me, transitional dressing comes down to two things: pairing the right fabrics and materials, and smart layering. A leather pant (as opposed to the typical tailored wool pant or dark denim) paired with an oversized silk blouse and a slingback kitten heel pump is appropriate for the office, while still being fun to wear to a dinner and party," Kerri recommends. "Layering—a slinky dress can be worn to the office with an oversized sweater, elongated blazer, and a loafer."

Do men have alternatives beyond the typical lounge suit?

"I love a clean and classic lounge suit in a dark hue, but men should feel more comfortable with trying out different colours and textures (especially for holiday dressing). A great place to start is sticking with the traditional dress code (suit and shirt and tie) but then having a little fun with one of the elements of that equation," Kerri relates.

Men can try swapping out their lounge suit jacket for a velvet smoking jacket, or pairing a two-piece suit with a tonal silk button-down and matching tie. Patterned or textured suits are both festive alternatives.

I want to wear something really special for New Year's Eve. Do you have any ideas?

Kerri says confidence is the key. "Wear items with impact that you feel comfortable in—nothing says 'special' more than a confidently dressed person, who is wearing the clothes (the clothes aren't wearing them). Also, accessories are a great way to add impact."

Look to the runway for inspiration. "My ultimate New Year's Eve look this year would pair a slouchy satin suit with a wool bustier—Prada has a great one that went down the runway over a printed button-down—and a crystal-embellished satin mule, with a standout clutch from Bottega Veneta."

I'm trying to shy away from buying and wearing things once. Are there any pieces I can wear throughout the season but then incorporate into my wardrobe in the future?

"My philosophy is to buy less and wear more. Well-made pieces easily transition from season to season," says Kerri. "Some wardrobe essentials that have carried me from season to season: Alexander Wang elongated black blazer, a great pair of leather (or faux-leather) trousers, cashmere sweaters from The Row, a bib-front cotton tuxedo shirt."

Suiting is timeless, polished, and extremely versatile. "This season's trendy slouchy two-piece suiting can transition from casual to formal, and be worn together or as separates," Kerri says.

For help acquiring the pieces recommended above, or for further advice, reach out to Kerri or Quintessentially's expert personal shopping team.

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