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Chelsea Boots

What makes a Chelsea boot? Named for the Chelsea neighbourhood of London in which they were popularized throughout the 'mod' scene in the fifties and sixties, these booties are a slip on ankle bootie with elastic side panels. Now they're a wardrobe staple, and have been reinvented over and over in a range of styles. Shop our Chelsea boots in their classic refined silhouette or in a more modern and edgy look on a chunky sole.

Becka

C$270.00

In stock

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Article code Becka-Brown Oiled-41

Round toed chelsea boot in dark brown oiled pull up leather with a clog construction on a wood grain rigid polyurethane sole featuring traditional staple finishing plus textile accent tabs, with Dansko's signature cushioned arch support

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Woden

Siri Waterproof

C$189.95 C$94.98

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Stylish urban rain bootie made from a waterproof natural and recycled rubber blend in two-tone grey and black plus fish leather accents on a platform track sole

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Woden

Siri Waterproof

C$189.95 C$94.98

ALOHAS

Armor

C$360.00 C$234.00

In stock

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Article code S00034-25-37

Cool and casual pull-on mid bootie in black leather with elastic panels for a snug fit and a platform track sole for an edgy (but comfortable) look

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ALOHAS

Armor

C$360.00 C$234.00

Feners

Le Jour

C$258.00 C$167.70

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Article code JOURNOIR-36

Modern chelsea boot in black leather with detailed stitching and a fitted elastic shaft on a rounded toe and chunky lugged rubber sole

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Feners

Le Jour

C$258.00 C$167.70

Miista

Flabia

C$380.00

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Article code Flabia-Black/Grey-36

Edgy pull-on mid calf boot in black leather with grey heel burnishing details and an elastic calf panel on a boxy toe and chunky block heel (by Miista's diffusion brand E8 by Miista)

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Dansko

Becka

C$270.00

In stock

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Article code Becka-Black-37

Round toed chelsea boot in black oiled pull up leather with a clog construction on a wood grain rigid polyurethane sole featuring traditional staple finishing plus textile accent tabs, with Dansko's signature cushioned arch support

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Sister x Soeur

Gemma

C$298.00 C$193.70

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Article code Gemma-Black Hi-Shine-36

Chelsea boot with a taller, fitted shaft in high shine polished black leather with a chunky but refined lugged sole and rounded toe

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Gemma

C$298.00 C$193.70

Woden

Siri Warm Waterproof

C$189.95 C$94.98

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Stylish rain bootie made from a waterproof natural and recycled rubber blend in colour blocked pale lavender and black plus fish leather accents on a platform track sole with cozy pile textile lining

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Woden

Siri Warm Waterproof

C$189.95 C$94.98

Sister x Soeur

Phelby

C$328.00 C$213.20

In stock

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Article code Phelby-Black Patent-41

Rounded toe chelsea boot in black genuine patent leather with moccasin-inspired stitch detailing on an ultra chunky track sole

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Sister x Soeur

Phelby

C$328.00 C$213.20

Sister x Soeur

Pippa

C$298.00 C$193.70

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Article code Pippa-Grey Patent-37

Round toed chelsea boot in light grey genuine patent leather on an ultra chunky track sole

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Sister x Soeur

Pippa

C$298.00 C$193.70

Wonders

G-6705

C$320.00 C$208.00

In stock

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Article code G6705-5000014-36

Pull-on ankle boot in black pebbled leather with a stylish high shine leather overlay panel along the back, on a lightweight but chunky sole and block heel

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Wonders

G-6705

C$320.00 C$208.00

Ateliers

Baxter

C$210.00 C$136.50

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Article code Baxter-Black-41

Chunky chelsea boot in black leather with a taller shaft and lugged sole

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Ateliers

Baxter

C$210.00 C$136.50

Bos. & Co.

Brunas

C$320.00 C$208.00

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Article code 30813-OL-36

Ankle boot in olive green leather with a taller elastic panelled shaft on a chunky sole and heel, winterized with a waterproof inner membrane

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Bos. & Co.

Brunas

C$320.00 C$208.00

Shoe the Bear

Iona Chelsea

C$219.95 C$142.97

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Article code Iona Chelsea-Black-37

Easy, cool everyday chelsea boot in black leather with contrast stitch details on a lugged platform sole

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Shoe the Bear

Iona Chelsea

C$219.95 C$142.97

Shoe the Bear

Posey Chelsea

C$259.95 C$168.97

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Article code STB2251-110-39

Chunky chelsea boot in black leather with a rounded toe on a lightweight platform track sole

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Shoe the Bear

Posey Chelsea

C$259.95 C$168.97

Woden

Siri Waterproof

C$189.95 C$94.98

In stock

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Article code WL957-Dark Olive-40

Stylish urban rain bootie made from a waterproof natural and recycled rubber blend in olive green with pops of orange plus fish leather accents on a platform track sole

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Woden

Siri Waterproof

C$189.95 C$94.98

Woden

Magda Track Waterproof

C$179.95 C$89.98

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Article code WL904-020-38

Perfect urban walking boot for the rainy season in a waterproof natural and recycled rubber blend with fish leather accents on a lugged rubber sole for great comfort and grip

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Woden

Magda Track Waterproof

C$179.95 C$89.98

Homers

Siena 21101

C$469.00 C$304.85

In stock

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Article code 21101-Black-36

Casual but cool chelsea boot in black pebbled leather with contrast stitch details on a chunky but lightweight lugged sole

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Homers

Siena 21101

C$469.00 C$304.85

Homers

Lys 21165

C$439.00 C$285.35

In stock

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Article code 21165-Black-36.5

Chelsea boot with personality in black genuine patent leather on a chunky lugged platform and heel, featuring white contrast stitching and a cute knitted accent back tab

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