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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.

Guidi PL1V Rubber Sole Front Zip Boot Black at WDLT117, Toronto
Guidi
PL1V Rubber Sole Front Zip Boot Black
$1,444Last one
WDLT117
Guidi NB07 Lace-up Back Zip Boot Black at WDLT117, Toronto
Guidi
NB07 Lace-up Back Zip Boot Blk
$1,358
WDLT117
Louis Vuitton Taurilon Leather Nano Steamer Bag Black at Utopia, Toronto
Louis Vuitton
Taurilon Leather Nano Steamer Bag Black
$1,272Pre-owned
Utopia
Louis Vuitton Keepall 55 Travel Bag Yellow Epi Leather at Utopia, Toronto
Louis Vuitton
Keepall 55 Travel Bag Yellow Epi Leather
$636Pre-owned
Utopia
Guidi Shoulder Bag Blk CA03 at WDLT117, Toronto
Guidi
Shoulder Bag Blk CA03
$1,376
WDLT117
Coor Multi Pocket Crinkle Leather Bag - Black at Due West, Toronto
COOR
Multi Pocket Crinkle Leather Bag - Black
$456
Due West
MM6 Maison Margiela 2-in-1 Knit Cardigan Dark Grey at WDLT117, Toronto
MM6 Maison Margiela
2-in-1 Knit Cardigan Dark Grey
$974Last one
WDLT117
Louis Vuitton Black Damier Signature Crewneck Knit Wool Sweater at Utopia, Toronto
Louis Vuitton
Black Damier Signature Crewneck Knit Wool Sweater
$424Pre-owned
Utopia
Goyard Boston 50 Bag Black at Utopia, Toronto
Goyard
Boston 50 Bag Black
$5,299
Utopia
Goyard Cap-Vert PM Bag Green at Utopia, Toronto
Goyard
Cap-Vert PM Bag Green
$2,120Lightly used
Utopia
MM6 Maison Margiela Tweed Blazer Black at WDLT117, Toronto
MM6 Maison Margiela
Tweed Blazer Black
$1,662Last one
WDLT117
MM6 Maison Margiela Bomber Jacket Brown at WDLT117, Toronto
MM6 Maison Margiela
Bomber Jacket Brown
$796$1,307Last one
WDLT117
Louis Vuitton Claudia Shoulder Bag MM Brown White Canvas Leather Murakami Multicolore Monogram at Utopia, Toronto
Louis Vuitton
Claudia Shoulder Bag MM Brown White Canvas Leather Murakami Multicolore Monogram
$1,060Pre-owned
Utopia
Goyard Belvedere PM Grey at Utopia, Toronto
Goyard
Belvedere PM Grey
$3,038Lightly used
Utopia
Song for the Mute Unisex Puffer Jacket Caramel at WDLT117, Toronto
Song for the Mute
Unisex Puffer Jacket Caramel
$579$1,692
WDLT117
Song for the Mute Unisex Puffer Jacket Black at WDLT117, Toronto
Song for the Mute
Unisex Puffer Jacket Blk
$579$1,692Last one
WDLT117
Goyard Boeing 25 Toilet Bag Sky Blue at Utopia, Toronto
Goyard
Boeing 25 Toilet Bag Sky Blue
$1,413Lightly used
Utopia
Goyard Boeing 25 Toilet Bag Green at Utopia, Toronto
Goyard
Boeing 25 Toilet Bag Green
$1,625
Utopia
Guidi 310 Front Zip Boot Black at WDLT117, Toronto
Guidi
310 Front Zip Boot Black
$1,376Last one
WDLT117
Les Deux Wool Rib Roundneck Sweater - Ivory at Due West, Toronto
Les Deux
Wool Rib Roundneck Sweater - Ivory
$197
Due West
MM6 Maison Margiela Logo Motif Balaclava White at WDLT117, Toronto
MM6 Maison Margiela
Logo Motif Balaclava White
$380Last one
WDLT117
Song for the Mute Fleece Relaxed Lounge Pants Mauve at WDLT117, Toronto
Song for the Mute
Fleece Relaxed Lounge Pants Mauve
$648New
WDLT117
Louis Vuitton Tailored Technical Wool Track Pants at Utopia, Toronto
Louis Vuitton
Tailored Technical Wool Track Pants
$707Lightly used
Utopia
MM6 Maison Margiela Numberic Patch Ribbed Scarf White at WDLT117, Toronto
MM6 Maison Margiela
Numberic Patch Ribbed Scarf White
$467
WDLT117

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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.