Winter city break outfits

These looks are for a few winter days in a city like Paris, London, Tokyo or New York. Each piece is named by its designer and sold by an independent boutique in Toronto. The newest looks come first.

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The pieces of A plaid wool jacket and wheat boots on a black form

A plaid wool jacket and wheat boots on a black form

The pieces of A striped rugby polo on a London mews

A striped rugby polo on a London mews

The pieces of A rose wrap coat in a London hallway mirror

A rose wrap coat in a London hallway mirror

The pieces of A red Nuptse and black Timberlands in the SoHo snow

A red Nuptse and black Timberlands in the SoHo snow

The pieces of A cream puffer and a knit balaclava in a New York lobby

A cream puffer and a knit balaclava in a New York lobby

The pieces of A grey double breasted coat over a cream cricket sweater

A grey double breasted coat over a cream cricket sweater

The pieces of A Patou camel jacket on a Paris morning

A Patou camel jacket on a Paris morning

The pieces of A pleated black blazer in a Paris hotel mirror

A pleated black blazer in a Paris hotel mirror

The pieces of A denim jacket with a shearling collar in Tokyo

A denim jacket with a shearling collar in Tokyo

The pieces of A printed Undercover jacket in a Tokyo lift mirror

A printed Undercover jacket in a Tokyo lift mirror

The pieces of A camel wool hooded jacket on a Copenhagen canal

A camel wool hooded jacket on a Copenhagen canal

The pieces of A camel puffer in a Vienna hotel mirror

A camel puffer in a Vienna hotel mirror

The pieces of A black blazer and green loafers in Marylebone

A black blazer and green loafers in Marylebone

The pieces of A brown bomber by a Tokyo window

A brown bomber by a Tokyo window

The pieces of Black faux fur and a ruffle mini in the West Village

Black faux fur and a ruffle mini in the West Village

The pieces of Knee high boots by the Meguro River

Knee high boots by the Meguro River

The pieces of A brown Lovepuffer with wool flares

A brown Lovepuffer with wool flares

The pieces of A navy Vernon with black wool

A navy Vernon with black wool

The pieces of A quilted trench for the city

A quilted trench for the city

The pieces of An ashen parka and a blue pouch

An ashen parka and a blue pouch

The pieces of Green wreaths and Grinch Kobes

Green wreaths and Grinch Kobes

The pieces of Paisley rugby and painter jeans

Paisley rugby and painter jeans

A dark brown RUOHAN knit meets wide UJOH trousers and pale aqua Guidi shoes. The complete outfit stands against a dark studio background.

Brown knit and aqua in London

Fine stripes and long UJOH sailor ties fall above an oak brown RUOHAN skirt and kiwi Guidi boots. The complete outfit stands against a dark studio background.

Sailor ties and oak in tokyo

Grey Masnada coat over a pale shirt and swamp cargo trousers, with birch and charcoal Hoka loafers against a pale studio wall.

A grey coat and swamp cargos in still air

An adult man wears a teddy knit and grey piping in New York.

A teddy knit and grey piping in Chelsea

MM6 Maison Margiela, Coperni, Toga Pulla jacket, skirt and pink shoes laid flat.

Anthracite and pink laid out in Tokyo

A black Patou top, white Nina Ricci tweed skirt and burgundy Guidi boots.

Black and tweed on brushed aluminium

Black paillette polo, taupe wrap cargo trousers and white piped boots on an ivory mannequin and silver disc.

Black paillettes and taupe wrap cargos on silver

A brown RUOHAN top, purple Issey Miyake skirt and burgundy Guidi shoes.

Brown drape and purple on green stone

Coperni pieces arranged on a New York outfit board.

Brown suede on a New York board

Helmut Lang, Yume Yume pieces arranged on a London outfit board.

Dune and smoke blue on a London board

A cream RUOHAN shirt sits above the uneven panels of an olive grey UJOH skirt and white Guidi boots. The complete outfit stands against a dark studio background.

Dust beige and olive folds in new york

An adult woman wears ecru and purple folds in Tokyo.

Ecru and purple folds in a Kiyosumi gallery

Davi, Sies Marjan, MM6 Maison Margiela pieces arranged on a London outfit board.

Floral cotton and teal on a London board

A green Carbone crochet shirt, dark khaki pleated trousers and white Guidi boots.

Green crochet in an oxblood tray

An adult woman wears green technical tailoring at a shoreditch canopy in London.

Green technical tailoring at a Shoreditch canopy

Homme Plisse Issey Miyake, Guidi pieces arranged on a New York outfit board.

Grey pleats and blue on a New York board

Grey printed pleated shirt, dark khaki pleated trousers and black Clarks shoes on a clay mannequin in a split alcove.

Grey pleats in a split clay alcove

An inky grey Homme Plisse shirt, pink Andersson Bell trousers and black Guidi derbies.

Inky pleats and pink on steel

Lime and grey Serapis sweater, teal corduroy trousers and cream Asics trainers on a silver mannequin and steel plinth.

Lime waves and teal corduroy on brushed steel

A lime Serapis sweater, navy Sulvam trousers and purple red Guidi boots.

Lime waves on charcoal felt

An adult man wears milk white pleats at an aoyama courtyard in Tokyo.

Milk white pleats at an Aoyama courtyard

An adult man wears navy seams and verdigris at a bloomsbury studio in London.

Navy seams and verdigris at a Bloomsbury studio

INTO THE EAST, Guidi pieces arranged on a Tokyo outfit board.

Paisley and cobalt on a Tokyo board

A dusty pink COOR cord jacket frames an ivory knit above black UJOH work trousers and grey Guidi derbies. The complete outfit stands against a dark studio background.

Pink cord and charcoal in new york

An adult woman wears purple pleats and camel boots in London.

Purple pleats and camel boots in Marylebone

An adult woman wears red cutouts and folded denim at a noho studio in New York.

Red cutouts and folded denim at a Noho studio

A cropped UJOH pinstripe jacket meets a black Helmut Lang midi dress and deep red Guidi boots. A woman stands against a dark studio background.

Sand tailoring and a black midi in london

Grey PRONOUNCE jacket and trousers with cream buttons and brown brogues on a dark sculptural mannequin above a cobalt pedestal.

Grey tailoring with rows of cream buttons

White folded MM6 camisole and black ribbed flared trousers with beige boots on a porcelain mannequin.

White folds and black ribbed flares on porcelain

A white Ellery dress, pale kiwi Guidi boots and a black Bao Bao handbag.

White frills in a blue ceramic tray

White woven panels run down a COOR shirt above curved charcoal trousers and Guidi shoes with metal heels. The complete outfit stands against a dark studio background.

White guayabera and charcoal in tokyo

Pale yellow LEJE dress with star straps and an asymmetric frill, with kiwi Guidi boots on a green mannequin.

Pale yellow frills against a green monolith

A yellow LEJE dress with asymmetric frills, black Guidi boots and an ivory backpack.

Yellow frills on black lacquer

Homme Plisse Issey Miyake, Guidi pieces arranged on a Tokyo outfit board.

Yellow pleats and green on a Tokyo board

Silver clasps fasten a dark brown COOR bomber above ice blue jeans and black Guidi derbies. The complete outfit stands against a dark studio background.

Brown bomber and ice denim in london

An ochre camel COOR leather jacket meets black knit, wide UJOH pleats and black Guidi boots. A man stands against a dark studio background.

Camel leather and black pleats in new york

A fango Masnada cardigan, brown Homme Plisse trousers and beige Guidi loafers.

Fango and brown on travertine

A plain Sunspel tee, Sies Marjan striped wool trousers and printed boots by both on a metal tray.

Beige cotton and wool on a London tray

A brown striped COOR polo, washed indigo jeans and metallic blue Guidi boots.

Brown stripes and blue boots for Nolita

A black COOR sweater, indigo jeans and burgundy Dr. Martens penny loafers on pale concrete.

Black knit and indigo in the East Village

A sage A.P.C. shirt and trousers with black Dr. Martens shoes with straps.

Sage cotton and black straps for Islington

A cream COOR cardigan, grey cargo trousers and Dr. Martens brogues in brown and grey leather.

Cream rib and grey cargos for Bloomsbury

An adult woman wears a short white Patou knit dress with a blue Telfar bag and python print Toga Pulla heels in New York.

A white knit dress and blue bag in Tribeca

A white MM6 jacquard top, Nina Ricci skirt with a black hem and blush Guidi boots.

White folds and a black hem for Chelsea

An adult woman wears a sage Magliano cardigan, navy Undercover cargos and cream Veja trainers in Tokyo.

A salvia cardigan and navy cargos in Daikanyama

An adult woman wears a brown Ujoh shoulder tied blouse with a willow Ruohan skirt and beige to aqua Guidi boots in London.

A brown tied blouse and willow skirt in Islington

An adult woman wears a white Acne Studios tee, washed grey Marine Serre jeans and cream Veja trainers, carrying a small blue Telfar bag on her shoulder in London.

A Stockholm tee and grey denim in Soho

An adult man wears a red tee with a white back print, black track trousers and cream running shoes in New York.

Red graphic and black nylon in Brooklyn

An adult man wears a black circle graphic tee, faded dark bootcut jeans and green suede loafers on a London street.

A circle graphic and dark denim in Dalston

An adult man wears a black circle graphic tee, pale blue cargo jeans and white trail shoes on a New York street.

Hand drawn black and blue cargo in Soho

A yellow Homme Plisse shirt, brown trousers with a stone print and metallic blue Guidi boots.

Yellow and stone pleats for Ebisu

A faceless display mannequin in a Tokyo showroom. An ivory COOR knit meets black Helmut Lang zip trousers and black Guidi derbies.

Ivory knit and black zips in Aoyama

A blue Pleats Please top, black pleated skirt and white Guidi booties.

Blue round pleats for Kagurazaka

A faceless display mannequin in a New York showroom. A pale yellow COOR cardigan sits over a white ribbed tank, black trousers and Guidi derbies.

Yellow argyle for a brooklyn studio

An adult woman wears a white Marine Serre tank, black Coperni cargos and white Veja trainers in Tokyo.

White ribbing and black cargos in Shimokitazawa

An adult woman wears a pale open knit over a white tank, brown and olive patchwork trousers and orange Guidi boots in London.

Bronze and rust in Hackney

An adult woman wears an olive Ujoh gathered dress with white Guidi shoes and a burgundy bag in New York.

An olive gathered dress in the West Village

An adult woman wears a white Leje denim crop top, black Ujoh culottes and fuchsia Toga Pulla heels in New York.

A white crop top and black culottes in Soho

An adult woman wears a brown Undercover polo and ivory trousers with silver Veja trainers in London.

A brown polo and white trousers in Marylebone

An adult woman wears a loose olive Ruohan slip dress with pink Veja trainers and a burgundy Bao Bao bag in New York.

Olive silk and pink trainers in Chelsea

An adult woman wears a charcoal Pleats Please high neck dress with white Guidi boots and a grey Bao Bao tote in Tokyo.

Charcoal pleats and a grey bag in Aoyama

An adult woman wears a long ecru Ruohan dress with beige and aqua Guidi boots and a grey tote in London.

An ecru dress and faded boots in Bloomsbury

A faceless display mannequin in a Tokyo showroom. A red COOR checked shirt meets faded carpenter jeans and black Guidi boots.

Red checks and work denim in koenji

A faceless display mannequin in a New York showroom. A brown UJOH pinstripe shirt sits above navy trousers with silver snaps and Guidi shoes with metal heels.

Chocolate and navy for a village dinner

A faceless display mannequin in a London showroom. A cropped grey UJOH shirt meets matching trousers with a black belt and black Guidi derbies.

Blue grey cotton for a soho showroom

A white MM6 jacquard top, black Pleats Please cocoon trousers and orange Guidi boots.

White jacquard and black pleats for Kuramae

A charcoal Pleats Please dress, pale blue Guidi shoes and a black Bao Bao handbag for a Ginza afternoon.

Charcoal pleats and a black bag for Ginza

A brown UJOH blouse, dune Helmut Lang trousers and grey Guidi boots for a Tribeca afternoon.

Brown ties and dune trousers for Tribeca

An adult man wears a dark khaki pea coat, black tee and beige sarouel trousers with pale green trainers in Tokyo.

Khaki and sand layers in Kuramae

An adult man wears a pale band collar shirt, light purple pleated trousers and black tassel loafers on a Tokyo street.

Flint and purple pleats in Jimbocho

An adult man wears a brown suede jacket, black tee and washed indigo jeans with yellow trail shoes in New York.

Brown suede and washed indigo in Chelsea

An adult man wears a pale blue denim jacket and cream corduroy trousers with brown boat shoes on a London lane.

Blue cotton and cream velour in Hampstead

A faceless display mannequin in a New York showroom. A white Coperni smock top drapes over black cargo trousers and grey Guidi derbies.

White smock and black cargo in chelsea

A faceless display mannequin in a London showroom. An ivory RUOHAN knit dress falls over deep red Guidi boots.

Pale drape and red for marylebone

A faceless display mannequin in a London showroom. Brown stripes run down an ivory COOR knit above dark jeans and black Guidi derbies.

Ivory collar and black denim in soho

A faceless display mannequin in a Tokyo showroom. Long shoulder ties fall from a brown UJOH blouse over mocha trousers and white Guidi shoes.

Brown ties and mocha for nakameguro

An adult man wears a grey down jacket and beige trousers with brown leather brogues on a London street.

Grey down and beige in Fitzrovia

An adult man wears an ecru stand collar jacket, black tee and grey pleated trousers with black tassel loafers in Tokyo.

Ecru and grey layers in Yanaka

An adult man wears a brown cotton jacket, khaki wool cargo trousers and low white strap shoes on a London street.

Brown cotton and khaki wool in Soho

An adult man wears a pale blue denim jacket, white tee and olive canvas trousers with black and cream trainers in New York.

Blue denim and olive canvas in Noho

A faceless display mannequin in a New York showroom. Three denim flowers sit across a Coperni mini dress above pale pink Guidi boots.

Denim flower and blush in soho

A faceless display mannequin in a Tokyo showroom. A black Coperni mini dress has a twisted neckline above white Guidi Chelsea boots.

Black twist for a daikanyama evening

An adult woman wears a black, blue and cream Daily Paper knit tee, blue Nina Ricci jeans and pale green Asics trainers, carrying a burgundy Bao Bao bag in Tokyo.

Striped knit and burgundy in Koenji

An adult woman wears a white red heart tee and black Amiri cargo flares with white and pink New Balance trainers, holding a small blue Telfar bag in New York.

Cargo flares and a blue bag in Nolita

An adult woman wears a charcoal Avavav graphic tee, blue Coperni spiral jeans and silver Veja trainers while holding a pink heart bag in Tokyo.

Spiral denim and a pink heart in Shibuya

A grey cropped tank and black cargos in Soho

An overhead flatlay of Homme Plisse Issey Miyake Basic Pleated Polo Shirt L.Grey, Homme Plisse Issey Miyake In the Shadow Pleated Trousers Shadow Black, Guidi 310 Front Zip Boots Metallic Blue.

Grey pleats and blue boots for Aoyama

An overhead flatlay of a cream COOR cardigan, washed black A.P.C. jeans and white Dr. Martens shoes with straps.

Cream rib and black denim for Marylebone

An overhead flatlay of Coperni Twisted Cut-out Jersey Dress Blk, Guidi 788Z Back Zip Mid Boots White, Guidi Mini Backpack DBP05.

Black jersey and white boots for Hackney

An adult man wears a black blouson, grey argyle cardigan and pale blue jeans with orange detailed trainers in New York.

A black blouson and grey argyle in Tribeca

An adult man wears an olive pleated jacket, grey polo and dark green pleated trousers with black trail shoes in Tokyo.

Army green pleats for a Nakameguro walk

An adult man wears a patchwork wool coat, navy tee and brown striped trousers with dark tassel loafers in London.

A patchwork coat and brown trousers in Islington

A faceless display mannequin in a New York showroom. A cropped black COOR knit meets faded indigo jeans and open back Guidi derbies.

Black knit and indigo for tribeca

A faceless display mannequin in a London showroom. A grey beige RUOHAN knit dress meets deep burgundy Guidi boots.

Ecru knit for a bloomsbury afternoon

A faceless display mannequin in a New York showroom. An olive brown RUOHAN slip dress meets dark brown Guidi ankle boots.

Olive silk for a tribeca supper

An adult man wears a brown graphic tee, khaki patchwork trousers and blue suede shoes on a Tokyo lane.

Brown graphics and khaki for Shimokitazawa

A tray holds a brown belted Coperni suede mini dress, a pair of blush Guidi boots and a small black Bao Bao bag.

Brown suede and blush for Hackney

A flatlay of a mint and green checked Pleats Please top and skirt with a pair of pale kiwi Guidi boots.

Green gingham pleats for Kagurazaka

A flatlay of a white striped UJOH sailor collar top, navy asymmetric skirt and a pair of white Guidi boots with metal heels.

Sailor stripes and navy for Bloomsbury

The pieces of Brown leather on an early SoHo morning

Brown leather on an early SoHo morning

The pieces of Green tailoring by a Bloomsbury square

Green tailoring by a Bloomsbury square

The pieces of Shadow pleats on a Jimbocho morning

Shadow pleats on a Jimbocho morning

An adult man wears a long grey coat, a pale blue striped shirt and charcoal trousers with brown brogues in London.

A grey coat and blue stripes in Marylebone

An adult man wears a black nylon biker jacket, ivory sweater and textured black trousers with low black strap shoes in New York.

Black nylon and ivory in the East Village

An adult woman wears a black Helmut Lang jacket, ivory Pleats Please top, olive flight trousers and white Veja trainers on a New York pavement.

Black shell and olive on a Nolita morning

An adult woman wears cream and blue Pleats Please layers, black cocoon trousers and pale blue Guidi shoes in a Tokyo courtyard.

Blue fold lines in Kiyosumi

Blue grey pleated tailoring and a pale grey polo are laid out above cream tassel loafers on pale stone.

Blue grey kersey pleats in Aoyama

A faceless grey mannequin wears a gold and green track jacket, wide brown track trousers and cream woven trainers.

Gold and green knit on the Lower East Side

An adult woman wears a powder blue RUOHAN dress and blue Yume Yume heels, holding a small black Bao Bao handbag in a New York gallery entrance.

Powder blue before a Chelsea gallery

An adult woman wears a praline Patou jacket, parchment cross front top and brown pleated skirt with white Guidi boots near a London stone entrance.

Praline and brown near Marylebone

An adult man wears a racing green jacket, ivory zip knitwear and curved beige trousers with brown boat shoes in London.

Racing green and beige at Broadway Market

A faceless grey mannequin wears a taupe coach jacket, grey sweater and cropped black trousers with brown running shoes.

Taupe coach layers for a Kuramae walk

Flat lay of a black Coperni jacket, a silver UJOH shirt, sand trousers and black Guidi derbies.

A business trip to Milan

Flat lay of a brown RUOHAN jacket, an off white Sulvam knit, blue Nina Ricci jeans and black Guidi boots.

A rainy evening in Paris

Flat lay of an umber RUOHAN coat, a pale greige Issey Miyake dress and dark oxblood Guidi boots.

A snowy night in SoHo

Flat lay of an onyx RUOHAN dress, a black Coperni jacket, black Coperni flats and a silver Chrome Hearts chain.

A night at the opera in Vienna

Flat lay of a black Y-3 jacket, a black UJOH top, black trousers and dark brown Undercover sneakers.

Japanese designers in black wool

Flat lay of a grey Denim Tears sweatshirt, grey track pants, blue Jordan sneakers and a grey Goyard pouch.

Outside the shows in Paris

Flat lay of a beige MM6 coat, a black Marine Serre top, a black Undercover skirt and grey Guidi boots.

Rain in Knightsbridge

Flat lay of a black Undercover jacket, a black Chrome Hearts hoodie and black trousers.

Tokyo at night in December

Flat lay of a rust Song for the Mute sweater, chocolate UJOH trousers and brown Burberry slippers.

Christmas dinner in London

Flat lay of a black Coperni dress, a black jacket, black KIMHEKIM sandals and a black Louis Vuitton bag.

Dinner in the West Village

Flat lay of a Sies Marjan coat, an ivory RUOHAN top, black Guidi boots and a pale gold Dior tote.

The Christmas market in Vienna

Flat lay of a chocolate brown MM6 shirt, black Nina Ricci trousers, black ankle boots and a lemon Stalvey bag.

Date night in the Marais

Flat lay of a black Helmut Lang dress, a black MM6 blazer, slate grey Guidi boots and a black Dior bag.

New Year's Eve in London

Flat lay of a black Issey Miyake jacket, a black sweater, black trousers, black Guidi loafers and a Tom Wood ring.

New Year's Eve in New York

Flat lay of a brown RUOHAN jacket, a grey MM6 cardigan, a black INTO THE EAST skirt and burgundy Guidi boots.

October in Saint-Germain

Flat lay of a sand UJOH blouson, a brown sweater, blue MM6 jeans and milk Rick Owens sneakers.

October on the Canal Saint-Martin

Flat lay of a camel Song for the Mute jacket, an off white Issey Miyake top and taupe RUOHAN trousers.

Sunday brunch in Daikanyama

Flat lay of a brown COOR coat, a brown sweater, charcoal Kody Phillips trousers and black Guidi derbies.

Chocolate brown at the members' club

Flat lay of a grey COOR coat, a black thom/krom shirt, black Avavav trousers and black Louis Vuitton derbies.

Opening night at the opera

Flat lay of a black Stutterheim jacket, a blue COOR sweater, black C.P. Company cargo pants and black boots.

A black raincoat for a rainy day

Flat lay of a black Y-3 jacket, black Walk in Paris jeans, black Nike sneakers and a black Dior bag.

A black track top for an October Saturday

Flat lay of a dark grey DIESEL jacket, a white Sunspel T-shirt, black Nudie Jeans and black Dr. Martens boots.

A grey biker jacket for a night out

Flat lay of a chocolate brown Nina Ricci jacket, black trousers, a black Goyard tote and black Guidi derbies.

A Saturday on Avenue Montaigne

Flat lay of a grey Issey Miyake dress, a black cardigan, black MM6 ballet flats and a yellow Louis Vuitton bag.

A flight to Paris

Flat lay of a black Issey Miyake blazer, a grey UJOH shirt, grey trousers and black Louis Vuitton sneakers.

A Monday in the City of London

Flat lay of a light taupe and brown Issey Miyake coat, an off white Sulvam knit and black Undercover cargo pants.

A snowy morning in Copenhagen

Flat lay of a dark navy Undercover jacket, an ecru Helmut Lang sweatshirt and indigo Gallery Dept. jeans.

A Sunday at Columbia Road

Flat lay of an olive Issey Miyake quarter zip, black trousers and grey New Balance sneakers.

An early flight out of Haneda

Flat lay of a brown COOR jacket, a black Sunspel T-shirt and black Acne Studios jeans.

A first date in shearling

Flat lay of a black Mackage jacket, a black C.P. Company sweater, black Y-3 trousers and black sneakers.

A late flight out of London

Flat lay of a beige RUOHAN jacket, an ivory Helmut Lang turtleneck, dark indigo MM6 jeans and black Guidi boots.

October in Copenhagen