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In winter, escaping the city for afternoon walks, outdoor fires and red wine poured well ahead of dinner helps soften the sting of chill in the air.

But bulky clothes appropriate for all those activities can be tricky to fit into an overnight bag. Here, a flight attendant, a boutique owner, a stylist and a designer explain how they pack for cold-weather weekends away.

‘Roll, don’t fold’

In her five years as an international flight attendant, Emma Shepardson has become something of an expert in packing.

“When it comes to weekend getaways, my biggest tips are to stick to one colour palette, focus on layers rather than bulky pieces and remember to roll, don’t fold,” she says. “It’s easier to compact everything and saves a lot of room.”

Shepardson wears her coat and boots on the plane since they take up the most luggage space and have the added benefit of being warm. “Domestic flights don’t have the luxury of blankets and planes are always cold,” she says.

She opts for versatile garments that cater to more than one activity whenever possible. Like this pair of pleat-front, tailored pants in technical thermal, poly-blend material by Lorna Jane. “They’re comfortable for the flight and still look stylish for dinner and drinks when you arrive,” Shepardson says.

‘Wear the same outfit all weekend’

James Smart’s all-black weekend packing list is best described as functional layering. “It’s only one weekend,” says the founder of Melbourne boutique Havn. “We’re thinking about an outfit – not outfits – with a number of layers that do the job for everything.”

The first thing Smart packs is a jacket. He suggests one made from a technical material such as a smooth, matt nylon that’s waterproof and functional, but in a cut that borders on professional – a mid- or three-quarter length with nice detailing through the cuffs and collar. That way, he says, “You can take it on a long walk outside but also wear it to the restaurant or the bar at night.” Similarly, he packs one pair of trousers that can take on the outdoors while looking stylish; think a “nice pair of jeans or a dense, twill pant that’s going to keep your legs warm but still look good in the evenings”.

If you “pretty much wear the same outfit all weekend, you don’t have to worry about unpacking your bags and shuffling around in your wardrobe and changing outfits,” he says.

The coat makes it

Julia McCarthy, the founder and designer of Friends with Frank, packs by the maxim: the coat makes the outfit.

She takes three coats with her when she travels in winter: a trenchcoat, a Barbour jacket and a classic wool coat. “It might seem excessive,” she says. “But once I have those coats or jackets right, then I can just add my in-between pieces as well.”

To fit everything into an overnight bag, she shares Shepardson’s method of wearing the bulkiest one (the wool coat) en route to her destination, folds up the trench and the jacket, then keeps her other packing lightweight.

She says the trench elevates casual outfits while the double-breasted black wool coat “will work with everything else”. The Barbour jacket is made from a heavy cotton drill that suits long walks on the beach, but “When I’m wanting to kind of look polished, I’ll zip that up and cinch the waist in and it kind of looks like a top.”

Plan to mix and match

When stylist Natalie Petrevski is packing for a weekend away, comfort is the first rule. “I love to not feel suffocated and like my body can breathe,” she says. “I’ve got some beautiful blended wool sets with a knitted polo and trousers for those moments when you’re hanging around the Airbnb with a tea and a book.”

As a stylist, modularity is her aim. Her packing list consists of cargo pants, tailored trousers in black or dark charcoal and oversized button-down shirts in cotton or cashmere blends that can be dressed up with jewellery for dinner. She takes one “long, vintage, wool and boxy” coat and then a softer bomber jacket. “I love oversized pieces in natural materials,” she says. “Things I can have on rotation and feel very put together in – and very warm.”

Load up on layers

To reduce bulk, lightweight garments in fine fabrics are high on all four interviewees’ packing lists. Shepardson includes simple, thin, long-sleeve tops that can be worn for walks in the countryside or paired with jeans and jewellery in the evening.

McCarthy favours long-sleeve brushed cotton tees and fine merino turtlenecks.

Smart starts with a merino wool T-shirt or thermal base layer, then adds a button-down cotton poplin shirt. He takes one heavier jumper – a sailor knit with a high neck and a quarter zip.

Stay strict about shoes

McCarthy and Petrevski limit themselves to a pair of sneakers and a pair of boots. Petrevski’s boots have a low heel, while her black-and-white Adidas sneakers match everything, she says.

McCarthy’s “really worn in” boots with a low wedge heel also “work with everything I have in my winter wardrobe”, she says.

Smart restricts his footwear even further. He brings a single pair of hiking boots that can take him from walks to winery lunches.