3 fashion insiders share their secrets to looking chic when the winter turns bleak

Photography by Peter Stigter
Photography by Peter Stigter

After an unusual late start to winter, the cold season is officially upon us. With the temperatures taking a dip in subzero territory overnight, we find ourselves a little lost in the wardrobe department. So rather than scramble to wear the closest warm clothing piece within arm’s reach, we sat down with three of the industry’s power women (Net-A-Porter’s Sarah Rutson, Banana Republic’s Marissa Webb and Longchamp’s Sophie Delafontaine) to pick their brains on how to dress appropriately, while looking good all season long. From posh-meets-pragmatic outerwear picks to next-level layering tips, scroll through to find out how fashion’s leading ladies are staying warm this season.

fashion insiders winter guide marissa webb
Photography by Arian Camilleri

Marissa Webb
Creative Director and Executive Vice-President of Design, Banana Republic
Frost cause: Man-style toppers and next-level layering

Marissa Webb would make a bad weather girl. “I obviously have no temperature filter…leather & layers all year round,” she wrote in an Instagram posted on Sept. 4 in the midst of a heat wave in New York. Snapped wearing second-skin leather pants, a white button-down, and a textured blazer tied around her waist, the striking Korean-born creative director and executive vice-president of design at Banana Republic (she also designs an eponymous contemporary line) is the poster girl for seasonless dressing—even when the mercury plummets. “I really embrace layers during the cold winter months,” she says. “I’ll have a blazer under another blazer—there are so many different ways to layer.” Webb fills her closet with chic variations of this working girl staple, magically turning these so-called practical pieces into street style stars. With 105,000 followers on Instagram, she also qualifies as the latter—talk about worldwide Webb.

A tomboy at heart, the New York-based designer favours tailored menswear-inspired pieces, like a classic herringbone coat, when it comes to outerwear. Length plays a starring role, too, especially when the sun goes down. “It’s not about a day or night coat,” she says. “Having a longer silhouette that goes below the knee works nicely with a longer skirt or wide-leg trousers. Trench coat-inspired pieces that are longer and have a bigger sweep help, too.” Her jam-packed schedule—she shows two collections during New York Fashion Week—means drama is strictly reserved for clothes, not conversations. Somehow, despite fashion’s dizzying Tasmanian Devil vibe, Webb always manages to look effortlessly chic—kind of like the cool girl next door.

The secret to her style? She’s often a one-hue wonder. “I’m obsessed with monochrome looks,” she says. “They make me feel strong and it’s the fastest, easiest trick for looking like you’ve actually put thought into your outfit.” Red is one of her head-to-toe hot-ticket colours, though her bright ideas also travel down to footwear. “A yellow rubber boot is pretty cute; I’d wear it with a monochrome grey outfit,” she says. When the snow falls, she slips into a pair of super sleek (and legit) equestrian boots by Ariat—perfect for galloping along the city streets in style. “I spend a lot of time outdoors because I have puppies,” she says. “Troy, my Pomeranian mix, gets cold sometimes and likes to wear my little knit hat—we share it.” Clearly, great taste runs in the family.

Photography by Peter Stigter

Sarah Rutson
Vice-President, Global Buying, Net-A-Porter
Frost cause: Posh-meets-pragmatic outerwear and globe-trotting boots

In the fashion biz, practicality and luxury rarely run in the same circles, but Sarah Rutson believes haute heartedly they can happily co-exist. The vice-president of global buying at luxury e-tailer Net-A-Porter (and former fashion director at Hong Kong-based luxury department store Lane Crawford) approaches dressing with the sensibility of a school teacher—though her A, B, Cs include Altuzarra, Balmain and Carven. “I’m a practical working woman; I’ve got a mortgage to pay and kids to put through school, so there’s a checklist,” she says, referring to her shopping strategy. When it comes to big winter purchases like outerwear, the cool factor is only one part of the equation. “Can your coat take you through October to a blizzard in February? Can it fit over extra layers? When you are making purchases early in the season, think about those practicalities,” she says.

Quality over quantity might be one of her mantras, but peek inside this fashion heavyweight’s closets and you’ll find both hanging there, including an Alexander McQueen parka and a Sacai biker jacket—two recent purchases that likely made their debut during fashion month. Starting in New York, ending in Paris and hitting London and Milan on the way, the biannual international ready-to-wear shows keep Rutson racking up the frequent flyer miles while navigating the fluctuating trends—and temperatures. “I have skirts, dresses and knits that can be worn with a bare leg and a high sandal, or with a suede high boot from Isabel Marant,” she says. “They fold up to nothing in my bag.” For layering, she relies on Comme des Garçons sweaters.

When it comes to runway trends this season, nothing has swept the competition quite like the cape. “As we’re buying thicker, more detailed knitwear you have to take into consideration what goes over it,” she says. “A cape is a wonderful example—you can pile a hell of a lot under it or you can wear a silk blouse.” As for cold weather accessories, Rutson has cozied up to Rag & Bone’s felt hats. “They’re chic and have a fantastic brim. They take you away from being in a woolly beanie,” she says.

A self-described city girl, Rutson also enjoys the great outdoors. “I’m inside so much and on planes, so I like to be out in nature,” she says. Think McQueen parka (hood up) and a pair of high top sneakers—practical magic, indeed.

fashion insiders winter guide sophie delafontaine

Sophie Delafontaine
Managing Director and Artistic Director, Longchamp
Frost cause: Luxe fabrics and cozy après-ski essentials

“I’m always cold,” says Sophie Delafontaine, managing director and artistic director of Longchamp. The third-generation heir of this French luxury label (her grandfather, Jean Cassegrain, founded the company in 1948) keeps cozy during the winter months in Paris cloaked in the finest fabrics. “I love leather, cashmere and silk,” she says. “I pay attention to the quality of material so I’m sure to be very warm.” Chic and elegant are two words that Delafontaine has on repeat when discussing her ideal winter wardrobe—one could say, given her je ne sais quoi, that these adjectives also fit her to a tee.

Since Longchamp expanded its global accessories empire (10 of its iconic Le Pliage totes are sold every minute) to include ready-to-wear and footwear, Delafontaine has been focused on creating beautifully cut luxe urban staples like the perfect leather jacket. “You can start to wear it in the fall, and then in the winter under your coat,” she says. When it comes to taking outerwear from oh to ooh-la-la, accessories are a surefire way to up your game. “If I wear an A-line silhouette, I like to have a ladylike bag,” she says. “If I have an oversized coat, I like a little clutch with it—it’s about the proportions of the coat and the bag.” Her day-to-day uniform is heavy on noir but she gets flashy with footwear. “I’ll wear all-black with metallic shoes that change from pink to yellow to orange,” she says. “I like to pair fancy accessories with a basic silhouette.” Her stellar collection of stoles (one of her fave labels is Douce Gloire), ranging from graphic to tie-dye, help brighten a grey, chilly day. “I love very long, thin ones or big squares. You can wear them in many ways—I wear one every day,” she says. (Après-ski included.)

Delafontaine’s favourite off-duty winter destination is Courchevel, a posh ski resort in the heart of Les Trois Vallées in the French Alps, where jetsetters like Victoria Beckham and Pippa Middleton hit the slopes. Besides her ski suit, which is black—quelle surprise—she packs several Brunello Cucinelli cashmere sweaters, jeans (black, dark navy and grey), and a leather or fur coat. “Ski holidays are with family and friends; I’m not glamorous,” she says, though her packing list would suggest otherwise. “When I go to Courchevel, I don’t take any high heels.” Trust the French to turn something flat into something flat-out fabulous.

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