Boots outfits

These looks are built around boots, worn with long skirts, trousers and layers. Each piece is named by its designer and sold by an independent boutique in Toronto. The newest looks come first.

Save to Pinterest

The pieces of Graffiti knee boots with a pleated mini

Graffiti knee boots with a pleated mini

The pieces of Camo Dr. Martens in a hallway mirror at night

Camo Dr. Martens in a hallway mirror at night

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 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 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 Canada Goose Langford parka on a snowy street

A Canada Goose Langford parka on a snowy street

The pieces of An orange Gucci x The North Face puffer over black

An orange Gucci x The North Face puffer over black

The pieces of Grey wool over black trousers

Grey wool over black trousers

The pieces of A cream parka on a park bench in Toronto

A cream parka on a park bench in Toronto

The pieces of A red parka on a snowy Toronto street

A red parka on a snowy Toronto street

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 A black Moncler in the chalet mirror

A black Moncler in the chalet mirror

The pieces of Black satin and a white mini for New Year's Eve

Black satin and a white mini for New Year's Eve

The pieces of Hiking boots and a balloon skirt

Hiking boots and a balloon skirt

The pieces of Knee high boots by the Meguro River

Knee high boots by the Meguro River

The pieces of A limestone parka in the lobby mirror

A limestone parka in the lobby mirror

The pieces of Patent boots and a denim panel

Patent boots and a denim panel

The pieces of Pink satin with grey suede boots

Pink satin with grey suede boots

The pieces of Sepia wool and grey pleats

Sepia wool and grey pleats

The pieces of Willow silk with faded boots

Willow silk with faded boots

The pieces of Bronze knit and purple red boots

Bronze knit and purple red boots

The pieces of Suede patchwork on an October afternoon

Suede patchwork on an October afternoon

The pieces of Tan corduroy in the fitting room

Tan corduroy in the fitting room

The pieces of A brown bunny knit on the plinth

A brown bunny knit on the plinth

The pieces of A brown Lovepuffer with wool flares

A brown Lovepuffer with wool flares

The pieces of A cardigan for New Year's Eve

A cardigan for New Year's Eve

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 Black Hybridge knit and coffee twill

Black Hybridge knit and coffee twill

The pieces of Black leather and a grey bow mini

Black leather and a grey bow mini

The pieces of Black tailoring with camouflage boots

Black tailoring with camouflage boots

The pieces of Black wool with blue glitter boots

Black wool with blue glitter boots

The pieces of Black wool and brown checks

Black wool and brown checks

The pieces of Black wool with a pearl bracelet

Black wool with a pearl bracelet

The pieces of Camel wool and brown tweed

Camel wool and brown tweed

The pieces of Charcoal knit and white boots

Charcoal knit and white boots

The pieces of Chocolate truffle red with brown trousers

Chocolate truffle red with brown trousers

The pieces of Coffee boots and a leather bomber

Coffee boots and a leather bomber

The pieces of Glen check wool and grey trousers

Glen check wool and grey trousers

The pieces of Padded wool and leopard boots

Padded wool and leopard boots

The pieces of Rosy brown with piped boots

Rosy brown with piped boots

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

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

Black discs catch the light on a Helmut Lang polo above sand UJOH culottes and blush Guidi boots. The complete outfit stands against a dark studio background.

Black shimmer and sand in toronto

Coperni pieces arranged on a New York outfit board.

Brown suede on a New York 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

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

Green crochet in an oxblood tray

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

Grey pleats and blue on a New York board

A lilac Carbone cardigan, swamp Masnada cargo trousers and black Guidi boots.

Lilac and swamp over cotton

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

Lime waves on charcoal felt

A moss UJOH blouse and light coffee trousers with white Guidi boots.

Moss and coffee over folded linen

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

Paisley and cobalt on a Tokyo board

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

Purple pleats and camel boots in Marylebone

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

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

Ivory Undercover jacket over a black tank and black wrap trousers, with grey block heel ankle boots in a charcoal studio.

White wool and black wrap trousers in still air

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

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 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 navy UJOH pocket jacket sits over a white ribbed tank, chocolate trousers and white Guidi Chelsea boots. The complete outfit stands against a dark studio background.

Navy pockets and chocolate in toronto

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

Brown stripes and blue boots for Nolita

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 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 brown Coperni plaid shirt with an attached hood, black Ruohan trousers and white piped Guidi boots in Toronto.

A brown hooded shirt and black trousers on Ossington

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

Yellow and stone pleats for Ebisu

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 a blue abstract Pleats Please top with beige pleated trousers and cobalt Guidi boots in Toronto.

Blue pleats and cobalt boots in the Annex

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

White jacquard and black pleats for Kuramae

A white LEJE crop top and Andersson Bell jeans with a double waist, worn with cobalt Guidi boots.

White crop and double waist denim on Queen West

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

Brown ties and dune trousers for Tribeca

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 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 Toronto showroom. A black Helmut Lang leather bubble dress meets orange Guidi ankle boots.

Black leather and orange in queen west

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

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 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 overhead tray of RUOHAN Patmos Dress Ecru, Guidi 310 Front Zip Boot Pink, BAOBAO Issey Miyake Valley Small Handbag Matte Black.

Ecru and blush for a Toronto gallery

An adult man wears a camel biker jacket, black knitwear and black corduroy trousers with suede boots in Toronto.

Camel leather and black corduroy on Bloor

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

A faceless display mannequin in a Toronto showroom. A pale blue RUOHAN dress falls in two long layers above white Guidi boots with silver heels.

Blue drape for a yorkville gallery

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 faceless display mannequin wears a grey Patou jacket, navy pleated top, ecru Helmut Lang jeans and white Guidi Chelsea boots.

Grey denim and ecru on Queen West

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 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

The pieces of Willow and charcoal on Ossington

Willow and charcoal on Ossington

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

Flat lay of a beige RUOHAN jacket, a light grey MM6 cardigan, ivory INTO THE EAST trousers and sand Guidi boots.

A cabin in January

Flat lay of a caramel Coperni dress, olive boots, a silver Chrome Hearts necklace and a black Bottega Veneta bag.

A cocktail party in Mayfair

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 a black Canada Goose jacket and a black Stone Island hoodie.

Black and oxblood for the cold

Flat lay of an olive MM6 Maison Margiela dress, red Guidi boots, a Louis Vuitton necklace and a dark oxblood bag.

Christmas Eve at home

Flat lay of a black Moncler jacket, a grey Undercover cardigan, black Issey Miyake trousers and black Guidi boots.

Winter in black and grey

Flat lay of a black Helmut Lang dress, a chocolate brown Nina Ricci jacket and dark oxblood Guidi boots.

A winter evening in leather and chocolate

Flat lay of a black Undercover jacket, black trousers, a black UJOH blouse, black Guidi boots and a black bag.

All black for a winter night

Flat lay of a black INTO THE EAST jacket, black shorts, a black Coperni top and burgundy Guidi boots.

Black velvet for a December party

Flat lay of a black Coperni jumpsuit, a black Undercover jacket, black Guidi boots and a Chrome Hearts safety pin.

New Year's Eve in black and silver

Flat lay of a black Mackage puffer, a black MM6 sweatshirt and black Song for the Mute jeans.

Winter streetwear for the snow

Flat lay of a black Mackage cape, a black Coperni gown, black Guidi boots and a black Chrome Hearts bag.

A black cape coat for the theatre

Flat lay of a Mackage jacket, a black Helmut Lang dress, black Guidi boots and a black Louis Vuitton bag.

A faux fur coat with western boots

Flat lay of a black Kody Phillips jacket, black Ellery trousers, black Guidi boots and a black COOR bag.

A leather bomber after dark

Flat lay of a black Mackage parka, a black Ottolinger skirt, black Guidi boots and a black Louis Vuitton bag.

A long black puffer in the rain

Flat lay of a black INTO THE EAST vest, black trousers and black MM6 ankle boots.

Black and gold for a holiday dinner

Flat lay of a black COOR jacket, a black Masnada sweater, black Helmut Lang trousers and black Guidi boots.

Black leather from gloves to boots

Flat lay of a graphite Helmut Lang jacket, black Chrome Hearts trousers and black Dr. Martens boots.

Black workwear with oxblood accents

Flat lay of a chocolate brown Ottolinger blazer, a chocolate skirt, dark brown Guidi boots and a brown RUOHAN bag.

Chocolate pinstripe for December

Flat lay of a black Coperni jacket, a Sies Marjan skirt, deep oxblood Guidi boots and a black Chrome Hearts bag.

Office siren in oxblood

Flat lay of a black Moose Knuckles parka, a black Moncler vest and a black Y-3 zip hoodie.

Three layers of black for January

Flat lay of a black Mackage jacket, black INTO THE EAST trousers, deep burgundy Guidi boots and a black Goyard bag.

A black wrap coat on a winter rooftop

Flat lay of a black Mackage bomber, a black UJOH skirt, black Guidi boots and a silver Serge DeNimes bracelet.

A bomber and western boots for the weekend

Flat lay of a brown COOR jacket, a black sweater and burgundy Enfants Riches Deprimes cargo pants.

A brown bomber for a weekend in the city

Flat lay of a black Supreme jacket, a black A.P.C. sweater, black COOR trousers and black Dr. Martens boots.

A faux fur hood for a winter rooftop

Flat lay of a black Mackage parka, black Helmut Lang trousers, blue Guidi boots and a black COOR bag.

A shearling parka for the holiday market

A leather jacket and red check for a concert

Flat lay of a black COOR jacket, a black sweater, black Amiri jeans and black Balenciaga boots.

Black jeans and a fishtail parka for a winter night

Flat lay of a black Coperni gown and dark oxblood Guidi boots.

A black gown and a rosary for Christmas

Flat lay of a black Kody Phillips jacket, a black Chrome Hearts sweatshirt and a black KIMHEKIM skirt.

A leather jacket for a fall date night

Flat lay of a black Mackage parka, black Nina Ricci trousers, oxblood MM6 boots and a black Glass Cypress scarf.

A long belted puffer for winter

Flat lay of a black G-Lab parka, dark indigo MM6 Maison Margiela jeans, red Guidi boots and a black COOR bag.

A waterproof parka for a rainy day

Flat lay of a dark navy Undercover shirt, a camel skirt, dark brown Guidi boots and a white Louis Vuitton bag.

Blue hour on the Corniche

Flat lay of an olive INTO THE EAST coat, a dark chocolate brown turtleneck and a pale gold skirt.

Dusk on the Beirut stairs

Flat lay of a black Coperni gown, a black Undercover jacket, black Guidi boots and a silver Tom Wood bag.

Opera night

Flat lay of a dark chocolate RUOHAN coat, a grey Nina Ricci sweater and dark anthracite MM6 trousers.

First snow in Yorkville

Flat lay of a camel RUOHAN jacket, an ivory Helmut Lang turtleneck, a camel skirt and beige Guidi boots.

Old Amman at golden hour

Flat lay of a black UJOH jacket, a silver UJOH shirt, a navy UJOH skirt, black Guidi boots and a grey Goyard bag.

Silver at the Kuwait Towers

Flat lay of a black Moncler jacket, a grey Undercover cardigan, charcoal trousers and black Dior ankle boots.

First snow in Toronto

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 an olive INTO THE EAST top, a brown RUOHAN skirt and dark brown Guidi boots.

Thanksgiving at home

Flat lay of a cream Moncler puffer, a taupe RUOHAN top, ivory INTO THE EAST trousers and white Guidi boots.

Après ski in Courchevel

Flat lay of a black Moncler puffer, a grey Chrome Hearts sweater and black Helmut Lang trousers.

Après ski in St. Moritz

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 chocolate brown INTO THE EAST jacket, a dark chocolate brown turtleneck and a black Litkovska skirt.

Ginkgo season in Seoul

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

October in Saint-Germain

Flat lay of an ivory INTO THE EAST coat, a cream MM6 top, ecru Helmut Lang jeans and off white Guidi boots.

Winter white in Zurich

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 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 beige MM6 jacket, a chocolate UJOH shirt, beige trousers, black Guidi boots and a Tom Wood ring.

A hotel bar, late

Flat lay of a black Coperni dress, an ivory INTO THE EAST coat, grey MM6 ankle boots and a grey Goyard pouch.

A winter wedding guest

Flat lay of a black INTO THE EAST jacket, a black Helmut Lang dress, black Guidi boots and a pale pink Gucci bag.

A Christmas party in the ballroom

Flat lay of a grey and beige Undercover blazer, a green Aime Leon Dore sweatshirt and brown trousers.

A weekend in the Cotswolds

Flat lay of a grey Nina Ricci sweater, a grey skirt, grey MM6 ankle boots and a pink Coperni crossbody bag.

A holiday party in Brooklyn

Flat lay of a camel Tiger of Sweden blazer, a black Balenciaga shirt and black Helmut Lang trousers.

A late dinner in Tribeca

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 brown Song for the Mute coat, a black UJOH shirt and dark charcoal Avavav trousers.

A brown coat for the theatre

Flat lay of a black Avavav dress, a black Moose Knuckles jacket and grey MM6 ankle boots.

A first date in faux fur

Flat lay of a black Moose Knuckles jacket, black Ottolinger jeans, oxblood MM6 boots and silver Maple earrings.

A shearling collar at a winter concert

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

October in Copenhagen