Navigating winter travel requires a delicate balance: you need to stay warm against drafty terminals and snowy arrivals, but you also need to breeze through security without wrestling with complex layers. The secret lies in strategic fabrics, elastic waistbands, and statement outerwear that doubles as a blanket mid-flight. From polished monochrome sets to the ever-trending ‘shacket’, we’ve curated the ultimate editorial guide to jet-setting in style this season.
The Oversized Teddy Coat Statement
Nothing screams ‘cozy luxury’ quite like a plush teddy coat. It’s effectively a socially acceptable robe that instantly elevates a basic base layer. Pair this voluminous outer layer with sleek leggings to balance the silhouette. It’s perfect for chilly departures and provides a soft cushion for napping against the plane window.
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The Elevated Monochrome Sweatsuit
The matching sweatsuit has graduated from loungewear to legitimate street style. The key to making this look expensive rather than sloppy is sticking to a monochromatic palette—think creams, camels, or soft greys. Throw a structured trench over it when you land to go straight to dinner.
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The Puffer Vest & Hoodie Combo
If you tend to overheat rushing to the gate but freeze on the plane, the puffer vest is your best friend. It keeps your core warm without restricting arm movement for luggage wrestling. Layer it over a thick hoodie and pair with fleece-lined leggings for the ultimate utilitarian travel uniform.
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The Knit Midi Dress & Combat Boots
Who says you can’t wear a dress to the airport? A ribbed knit midi dress offers as much stretch as yoga pants but looks infinitely more polished. Pair it with sturdy combat boots to add an edge and make running for your connection easier. It’s a ‘one-and-done’ outfit that packs minimal bulk.
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The ‘Rich Mom’ Cardigan & Trousers
Channel effortless wealth with a pair of wide-leg knit trousers and a long, duster cardigan. This look is all about drape and flow. It’s non-restrictive for long-haul flights but looks sophisticated enough for a business class upgrade. Stick to earth tones to keep the vibe grounded.
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Leather Leggings & Oversized Knit
Faux leather leggings are the holy grail of winter travel. They wipe clean (spilled coffee happens), they hold you in, and they look instantly dressy. Balance the sleek bottom with a massive, chunky cable-knit sweater to play with proportions. Add a beanie for bad hair days.
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The Shacket & Turtleneck Layering
The ‘shacket’ (shirt-jacket) is ideal for transitional travel climes. Wear a fitted turtleneck underneath to lock in warmth without bulk. This combination works perfectly with straight-leg jeans or joggers. It’s the Pacific Northwest vibe that works globally.
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The Blazer & Hoodie Street Style
Inspired by off-duty models like Hailey Bieber, layering a structured blazer over a casual hoodie is the ultimate high-low fashion mix. It says ‘I mean business, but I also want to be comfortable.’ Pair with biker shorts if you’re heading somewhere warmer, or leggings for the cold.
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The Sherpa-Lined Denim & Joggers
Denim jackets are usually too cold for winter, unless they are lined with sherpa. This gives you that classic Americana look with actual insulation. Since denim is rigid, keep the bottom half soft with high-quality grey joggers. It’s durable, casual, and timeless.
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The Poncho Wrap & Skinny Jeans
A poncho is essentially a socially acceptable blanket that you can wear. It makes getting through security a breeze—just lift it off—and it keeps you enveloped in warmth on the flight. Since the top is voluminous, pair it with skinny jeans or fitted trousers to maintain shape.
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The Bomber Jacket & Cargo Pants
Utility meets fashion. Cargo pants are trending hard right now, and their pockets are genuinely useful for stashing boarding passes and lip balm. Pair with a satin or padded bomber jacket for a look that is cool, edgy, and incredibly practical for winter transit.
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The Blanket Scarf & Trench Coat
The classic beige trench is a travel icon for a reason—it resists water and wind. But for winter, you need to accessorize it with a massive blanket scarf. This adds texture and vital neck warmth. Keep the layers underneath light so you don’t overheat when you land.
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The Cashmere Crew & Maxi Skirt
For those who prefer not to wear pants, a heavy jersey or knit maxi skirt is a comfortable alternative. It allows for full freedom of movement and feels like wearing pajamas. Elevate it with a soft cashmere crewneck sweater for a look that feels artisanal and bohemian yet cozy.
