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Winter City Break Outfits

Warm coats, heavy knits, tailored trousers, and walking boots from independent boutiques for a weekend away in cold weather.

Winter city break outfits combine insulated outerwear, heavy knitwear, and walkable leather boots for traveling through cold streets on foot. Oversized coats over relaxed trousers establish clean lines while keeping wind out. Dense wool and down hold in heat on cold, wet days, in shades of black, blue, and grey.

Mackage began in Montreal in the late nineties with outerwear in leather, down and wool. Moose Knuckles, another Montreal label, makes down parkas and jackets. Guidi has tanned leather in Pescia, in Tuscany, since the eighteen nineties, and it began making its own shoes in the early two thousands by recreating old workers' shoes and hiking boots.

Pair a cropped puffer coat with pleated wool trousers and stacked sole boots, and layer cashmere sweaters under shearling outerwear for long gallery afternoons. Due West in Toronto brings most of this wall, with down parkas and jackets from Moose Knuckles, Mackage and Canada Goose, and COOR. WDLT117 in Toronto brings Guidi zip boots and MM6 Maison Margiela ankle boots, and Utopia in Toronto adds Goyard and Louis Vuitton bags for the trip, most of them pre owned.

MM6 Maison Margiela Anatomic Ankle Boots Black at WDLT117, Toronto
MM6 Maison Margiela
Anatomic Ankle Boots Blk
$977
WDLT117
MM6 Maison Margiela Anatomic Leather Ankle Boots Grey at WDLT117, Toronto
MM6 Maison Margiela
Anatomic Leather Ankle Boots Grey
$887
WDLT117
RUOHAN Skara Jacket Obsidian at WDLT117, Toronto
RUOHAN
Skara Jacket Obsidian
$1,914Last one
WDLT117
RUOHAN Skara Jacket Dune at WDLT117, Toronto
RUOHAN
Skara Jacket Dune
$1,050
WDLT117
Goyard Cap-Vert PM Bag Green at Utopia, Toronto
Goyard
Cap-Vert PM Bag Green
$2,826
Utopia
Goyard Cap-Vert PM Shoulder Bag White at Utopia, Toronto
Goyard
Cap-Vert PM Shoulder Bag White
$1,766Pre-owned
Utopia
Guidi 796ZI Back Zip Metal Heel Mid Boot Black at WDLT117, Toronto
Guidi
796ZI Back Zip Metal Heel Mid Boot Black
$1,484Last one
WDLT117
Guidi 796ZI Back Zip Metal Heel Mid Boot White at WDLT117, Toronto
Guidi
796ZI Back Zip Metal Heel Mid Boot White
$1,484
WDLT117
RUOHAN Umber Raas Coat at WDLT117, Toronto
RUOHAN
Umber Raas Coat
$2,279
WDLT117
RUOHAN Loess Cocoon Jacket Beige at WDLT117, Toronto
RUOHAN
Loess Cocoon Jacket Beige
$2,316Last one
WDLT117
Guidi PL1WZ Stacked Heel Front Zip Dk. Brown at WDLT117, Toronto
Guidi
PL1WZ Stacked Heel Front Zip Dk. Brown
$1,444
WDLT117
Guidi PL1WZ Stacked Heel Front Zip Cobalt Blue at WDLT117, Toronto
Guidi
PL1WZ Stacked Heel Front Zip Cobalt Blue
$579$1,409
WDLT117
UJOH Slit 6BW Jacket Black at WDLT117, Toronto
UJOH
Slit 6BW Jacket Blk
$1,299Last one
WDLT117
Mackage Womens Wind Jacket Mai - Black/Cream at Due West, Toronto
Mackage
Womens Wind Jacket Mai - Black/Cream
$841
Due West
Moose Knuckles Womens Down Bomber Debbie Shearling - Black/Natural at Due West, Toronto
Moose Knuckles
Womens Down Bomber Debbie Shearling - Black/Natural
$915Last one
Due West
Moose Knuckles Womens Down Bomber Debbie Shearling - Black/Black at Due West, Toronto
Moose Knuckles
Womens Down Bomber Debbie Shearling - Black/Black
$774$915
Due West
Mackage Womens Lite Jacket Patsy-BXZ - Black at Due West, Toronto
Mackage
Womens Lite Jacket Patsy-BXZ - Black
$954
Due West
Mackage Womens Lite Jacket Patsy-FZ - Black at Due West, Toronto
Mackage
Womens Lite Jacket Patsy-FZ - Black
$954
Due West
Goyard Anjou Tote Mini Green at Utopia, Toronto
Goyard
Anjou Tote Mini Green
$3,179
Utopia
Louis Vuitton Taurilon Leather Nano Steamer Bag Black at Utopia, Toronto
Louis Vuitton
Taurilon Leather Nano Steamer Bag Black
$1,272Pre-owned
Utopia
Mackage Womens Lite Jacket Patsy-BXZ - Cream at Due West, Toronto
Mackage
Womens Lite Jacket Patsy-BXZ - Cream
$954
Due West
Song for the Mute Flight Jacket W Camel at WDLT117, Toronto
Song for the Mute
Flight Jacket W Camel
$1,050
WDLT117
Louis Vuitton Keepall 55 Travel Bag Yellow Epi Leather at Utopia, Toronto
Louis Vuitton
Keepall 55 Travel Bag Yellow Epi Leather
$636Pre-owned
Utopia
Goyard Cap-Vert PM Bag Green at Utopia, Toronto
Goyard
Cap-Vert PM Bag Green
$2,120Lightly used
Utopia

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Common questions

What should you pack for winter city break outfits?
Pack a stormproof coat, heavy wool sweaters, relaxed trousers, and sturdy walking boots. Down and thick knitwear layer easily without adding much bulk in a carryall.
Which footwear works best for walking cold streets?
Choose thick soled leather boots treated against road salt and winter moisture. Guidi, which works in horse leather, makes front and back zip boots, including styles on rubber soles, which grip wet stone better than leather.
How do you style cold weather layers without looking bulky?
Anchor an oversized wool jacket with structured straight trousers and low profile knitwear. Balancing volume across your shoulders with tailored lines keeps the silhouette sharp through whole days outdoors.