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Wondering what to wear this winter? Here are five stylish, cold-weather outfits ideal for Canadian winters. Styled to fit mild temperatures, the polar deep freeze, or anything in-between, these looks are fresh and inspired by chic street-style trends we’re loving. From outerwear, bottoms, shoes and accessories that are everywhere right now, here are this season’s coziest, fashion-forward looks you can actually wear and feel great in.
1) Monochromatic in merlot: The Super Puff Long + wrap sweater + velvety lace maxi skirt
Yes, monochromatic dressing is still a trendy, easy way to pull your look together. Pick a colour and build in shades and hues around it (it’s totally fine if they aren’t a perfect match, so long as they are visually in the same family). The trick with monochromatic looks is to play with textures to add dimension to your look. We’re especially loving this deep burgundy-merlot colour that’ll add richness and luxury to any grey day.
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Aritzia’s longer Super Puff delivers peak winter performance and is already part of a cult favourite lineup. Engineered for warmth to –40°C/–40°F, its signature maximalist silhouette traps serious heat while looking effortlessly stylish. This cold-weather essential keeps you super warm exactly where it counts.
This V-neck wrap sweater pairs a flattering tie-waist silhouette with luxurious comfort. Knitted from Aritzia’s SoftSpoke™ merino wool–cashmere yarn, it feels plush and exceptionally soft. Finished with ribbed trim and a smooth Jersey-stitch drape, it delivers an elevated, effortlessly cozy layer for everyday winter wear.
This stretch-lace piece is crafted with velvety detailing and finished with delicate scalloped, fringed edges. A silky, stretch-jersey partial lining adds comfort without losing its sheer elegance, while the straight fit and inner elastic waistband create an comfortable-yet-flattering silhouette, perfect for dressing up this winter.
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These classic pumps deliver all-day comfort with a flexible outsole and rebound footbed that adapts to your every step. Memory-foam cushioning and advanced shock absorbers protect your heel and forefoot, while breathable lining keeps things ventilated. With interlock stability technology, non-slip traction and a high-density flexible innersole, they’re built for endurance – no matter where your day or night take you.
This seamless two-in-one necklace solves all your stacking struggles, pairing dual chains with a luminous natural opal pendant. Crafted from 94% recycled sterling silver and finished with thick 18K gold plating, it’s both hypoallergenic and elevated – an easy, polished piece that adds instant shine to any winter outfit.
2) Cozy chic: Wide leg lounge pant + bold hoop earrings + classic tall chalet UGG
Dazzle in the snow even as you protect your peepers from the brightest winter days. White is no longer taboo past Labour Day or during our long winters. By styling it specifically to suit the season, you can embrace both the look of the coziest days and still look effortlessly stylish.
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This faux-fur jacket by Aussie brand ELLIATT features faux-leather accents, a front zip and a relaxed silhouette with a ruched waist still giving it that cinched look. The plush texture and edgy details delivers a statement-making look with effortless, high-glam appeal.
Comfortable as they are stylish, the extra-wide leg pant comes in a lovely egret colour, perfect for lounging around a chalet or venturing out into the snow over a cozy weekend. It’ll fit inside any capsule wardrobe because it’s made to last with the Varley brand’s high-quality fabrics, taking you not just through this season, but to others that follow.
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These tiny statement earrings offer the look of double hoops in one seamless design. Ultra-light and comfortable to wear, they add shine without weighing you down. Finished in 14k gold, they bring a modern, minimalist touch to everyday style – perfect for effortless stacking or worn alone.
Add this classic Herschel Elmer beanie in a soft blush to complete the look while keeping warm.
These cozy UGG boots channel mountain-side charm with their plush sheepskin upper and criss-cross lacing. Soft UGGplush™ lining keeps every step warm, while the lightweight sugarcane EVA outsole adds cushy comfort. Perfect for après-ski moments, chilly strolls and everything in between, they’ll bring you dreamy winter comfort to everyday wear.
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Don’t overlook those sparkling peepers: These Michael Kors aviator sunglasses feature an olive-tinted transparent frame with matching mirrored lenses for a sleek, modern look. Designed with a Universal Fit, they offer better grip and comfort on a wide range of face shapes. With full UV protection and a protective case included, they’re a stylish, practical winter accessory.
The Michael Kors Cyprus sunnies are another great option to complete this look.
3) Colourblock for contrast: Bright puffer jacket + Lime green beanie + Stretch barrel jean + Classic Chelsea boot
Bring bright colours into dark, dreary days by playing with colourblocking – a design technique whereby you combine two or more colours that call each other out. You can play with complementary colours (colours that are directly opposite to each other on the colour wheel), analogous colours (colours that are next to each other on the colour wheel), or even triadic colours (three colours, evenly spaced on the colour wheel).
This cropped puffer pairs a relaxed, easy fit with serious cold-weather performance. Made from water-resistant, RCS-certified recycled polyester, it’s fully quilted and insulated for dependable warmth. The wide quilting, concealed zipper, stand collar and adjustable hem create a clean, minimalist look that styles effortlessly with high-waisted winter staples.
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For an even bolder winter look, we absolutely adore this Beach Riot Jojo Bow Puffer Jacket from Anthropologie as well (now on sale for $130).
This versatile knit beanie brings cozy warmth with its double-layer, thermal design and stretchy fit that adapts to most head sizes. Wear it cuffed, slouchy or fisherman-style for different looks. With a range of colours and easy pairing with winter layers, it’s a go-to accessory for cold-weather outings and everyday wear.
The Bella Stretch Barrel Jeans elevate everyday denim with a high-rise waist and structured barrel leg for a modern, flattering silhouette. Made from premium, organic-cotton denim, they offer comfort, support and an incredibly soft feel. Stylish and versatile, these jeans are a go-to wardrobe staple you’ll reach for season after season.
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These heeled Blundstone Chelsea boots blend classic style with modern versatility. Crafted from genuine leather with side elastics and a removable cushioned footbed, they deliver comfort and effortless wear. The embossed non-skid sole and included extra pair of soles make them practical, while the 2″ heel adds a polished, fashion-forward touch.
This open-design Mejuri ring celebrates intentional, flowing movement, with each curve reflecting a unique angle. Crafted from 95% recycled sterling silver, it’s hypoallergenic, strong and highly durable – a minimalist yet striking piece that effortlessly elevates any winter accessory rotation.
4) An Olympian Effort: Team Canada Women’s Wunder Puff + oversized hoodie + ultrasoft high-rise leggings + beanie
Winter is our sport. Before the watch parties pick up, support Team Canada in the 2026 winter games and invest in a piece of Canadian history.
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To be worn by Team Canada on the podium, this premium down jacket combines performance and style. Water-repellent and windproof, it features 600-fill-power RDS-certified goose down for exceptional warmth. Its relaxed, layer-friendly fit allows for customizable comfort, making it a winter essential for both outdoor adventures and everyday cold-weather wear.
The Team Canada Women’s Wunder Puff Large-Hood Jacket Shine is another great option you have here and complete the look with the Team Canada Future Legacy Warm Revelation Beanie, scarf and crossbody bag.
This oversized hoodie adds to your look without overcomplicating the styling. Made from a soft cotton-polyester blend with fleece lining it’ll keep you warm, while the kangaroo pocket adds practicality. With a classic, unisex design, it pairs easily with casual pants or leggings, making it a versatile essential for everyday wear and outdoor activities.
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We also love Aritzia’s Cozy Sweatfleece Mega Hoodie option here, if you have room in your budget.
Designed to do double duty – both for yoga and and as casual pants – these crossover waist leggings are made from Lulu’s performance sueded fabric to deliver softness and warmth when outside is anything but.
This handcrafted Mejuri ring is a chic good-luck charm and ideal stacking piece. Made from 94% recycled 14K solid gold, it’s hypoallergenic, water-resistant and built to last. Elegant and meaningful, it adds a touch of refined sparkle to any winter accessory collection.
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5) Wild about winter: Cashmere coat + leopard pleated skirt + tall leather boot + gloves
Add a touch of Parisian elegance to the mix with Aritzia’s Maxine Coat. It pairs refined tailoring with winter-ready warmth. It’s crafted from soft wool-cashmere with a herringbone weave and it features a double-breasted wrap silhouette, structured shoulders and trench-inspired details for ultimate comfort. With an ultra-thin suede interlining for wind protection, it’s a luxurious, stylish layer for cold-weather sophistication.
We also do like Aritzia’s Chalice UnReal Leather coat to complete the outfit (and – bonus – it’s currently on sale).
The leopard skirt brings effortless luxury to your wardrobe with its lightweight, fluid chiffon and silky built-in lining. Featuring a comfortable covered elastic waistband, this sheer, flowing skirt adds a touch of Scandi elegance and playful leopard print to any winter outfit, making it a versatile statement piece.
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The Sarria Tall Boots from Simons x Maguire combine sleek design with everyday wearability. Crafted from smooth genuine leather with an inner-side zip and padded footbed, they offer comfort and ease. Made in Spain, the 12″ shaft and 2″ heel deliver a polished, versatile look perfect for elevating winter outfits.
UGG’s Luxe Gloves combine soft cashmere-blended wool on the back with supple leather on the front for warmth and style. They’re fully lined, feature a brushed polyester interior and a signature leather logo clip. Elegant and practical, these gloves are a winter-ready accessory that pairs effortlessly with any cold-weather outfit.
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Women’s Long Winter Down Coat – $79.99
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Men’s Windproof Winter Jacket – $89.99
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