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Menswear style guide

How to Style Ankle Boots for Men

31 complete outfits with ankle boots, put together by MISE. In our looks they are worn most often with trousers, polos, knitwear and black knitwear. They work best for the office and travel. The pieces below go from €90 to €830, from Ulanka, COS, BOSS and Massimo Dutti.

Charcoal Merino, Navy Wool Trousers
Charcoal Merino, Navy Wool Trousers
3 pieces, 3 stores, €560
Extra-fine merino crew neck jumper
Sunspel
€225
Elasticated Wool Trousers
Sandro
€245
Edward Brown Suede Chukka Boots
Ulanka
€89.99
Black Knit, Grey Trousers
Black Knit, Grey Trousers
3 pieces, 3 stores, €493
Zanone Cotton Crewneck Sweater Black
Zanone
€213.95
Cotton blend slim fit pants grey
Massimo Dutti
€80
Leather Chelsea Boots
COS
€199
Ecru Henley, Light Denim
Ecru Henley, Light Denim
3 pieces, 3 stores, €490
Slim Ribbed Henley Off-White
COS
€45
Slim-fit jeans light blue
Sandro
€195
Suede Chelsea boots
BOSS
€250
Navy Long Sleeve, Beige Gabardine
Navy Long Sleeve, Beige Gabardine
3 pieces, 3 stores, €529
Long Sleeve Heavyweight T-Shirt Navy
Sunspel
€150
Slim Fit Gabardine Trousers Light Beige
BOSS
€149.95
Suede Desert Boots Black
COS
€229
Black Turtleneck, Slate Chinos
Black Turtleneck, Slate Chinos
3 pieces, 3 stores, €554
Wool turtleneck sweater
Calvin Klein
€114.90
Slim-fit chino in slate blue
Sunspel
€210
Square-toe leather ankle boots
COS
€229
Black Roll Neck, Navy Wool
Black Roll Neck, Navy Wool
3 pieces, 3 stores, €489
Extra-Fine Merino Turtleneck Black
BOSS
€169.95
Wool Slim-Fit Straight-Leg Trousers Navy
COS
€129
Leather Blucher Ankle Boots
Massimo Dutti
€190
Black Tee, Brown Harrington
Black Tee, Brown Harrington
4 pieces, 4 stores, €847
Cotton Crew-Neck T-Shirt
Lemaire
€212.75
Merino Wool Harrington Jacket
COS
€129
Elasticated Straight-Leg Trousers
Sandro
€225
Leo Suede Desert Boot
Castañer
€280
Ecru Long Tee, Faded Jeans
Ecru Long Tee, Faded Jeans
3 pieces, 3 stores, €435
100% Cotton Long Sleeve T-Shirt
Massimo Dutti
€50
Slim-fit jeans light blue
Sandro
€195
Leather Chelsea Ankle Boots
Massimo Dutti
€190
Navy Knit Polo, Black Trousers
Navy Knit Polo, Black Trousers
3 pieces, 3 stores, €454
Long-Sleeved Knitted Polo Shirt
Sandro
€225
Wool Slim Fit Straight Leg Trousers
COS
€99
Split suede moc toe chukka boots
Massimo Dutti
€130
Olive Roll Neck, Grey Chukkas
Olive Roll Neck, Grey Chukkas
3 pieces, 3 stores, €479
Slim Wool-Jersey Roll-Neck Top
COS
€59
Elasticated Wool Trousers
Sandro
€245
Suede Chukka Boots
Pollini
€174.97
Cream Knit Polo, Sand Trousers
Cream Knit Polo, Sand Trousers
3 pieces, 2 stores, €939
100% Wool Knit Polo Sweater
Massimo Dutti
€70
Dylan Cotton Twill Trousers
A.P.C.
€229.14
Leather Lace-Up Ankle Boot
Our Legacy
€640.04
Charcoal Crew, Brown Straight Leg
Charcoal Crew, Brown Straight Leg
3 pieces, 3 stores, €834
Slim Merino Wool Crew Neck Charcoal
COS
€69
Straight-Leg 5-Pocket Trousers Brown
Sandro
€245
Leather Ankle Boot Dark Brown
Our Legacy
€519.93
Brown Knit Polo, Navy Trousers
Brown Knit Polo, Navy Trousers
3 pieces, 3 stores, €726
100% merino wool knit polo sweater
Massimo Dutti
€70
Wool trousers
Sandro
€245
Chelsea boot brown
Doucal's
€411.46
Grey Cashmere, Forest Chinos
Grey Cashmere, Forest Chinos
3 pieces, 3 stores, €1139
Cashmere crew neck jumper
COS
€179
Slim-fit chinos in stretch cotton
BOSS
€129.95
Church's leather chelsea boots
Church's
€829.91
Navy Merino, Brown Boots
Navy Merino, Brown Boots
3 pieces, 3 stores, €1144
Extra-Fine Merino Jumper in Navy
Sunspel
€225
Wool Suit Trousers
Sandro
€245
Calf Leather Square Toe Ankle Boot
Lemaire
€673.95
Black Merino, Navy Wool
Black Merino, Navy Wool
3 pieces, 3 stores, €1027
Extra-Fine Merino Crew Neck Jumper
Sunspel
€225
Wool Trousers
Sandro
€285
Leather Ankle Boot
Our Legacy
€516.64
Loden Long Tee, Camel Trousers
Loden Long Tee, Camel Trousers
3 pieces, 3 stores, €624
Long sleeve heavyweight classic t-shirt in loden green
Sunspel
€150
Elasticated wool trousers
Sandro
€245
Square-toe leather ankle boots
COS
€229
Loden Half Zip, Blue Slim Trousers
Loden Half Zip, Blue Slim Trousers
3 pieces, 3 stores, €605
Extra-fine merino half zip in loden green
Sunspel
€295
Slim-fit trousers in four-way stretch fabric
BOSS
€179.95
Split suede chukka boots
Massimo Dutti
€130
Taupe Cashmere, Suede Chukka
Taupe Cashmere, Suede Chukka
3 pieces, 3 stores, €720
Cashmere crew neck jumper, taupe
Sunspel
€410
Slim-fit trousers in four-way stretch fabric
BOSS
€179.95
Split suede moc toe chukka boots
Massimo Dutti
€130
Grey Cashmere, Slate Chino
Grey Cashmere, Slate Chino
3 pieces, 2 stores, €849
Cashmere crew neck jumper grey melange
Sunspel
€410
Slim fit chino slate blue
Sunspel
€210
Suede desert boots black
COS
€229
Taupe Cashmere Polo, Navy Suede
Taupe Cashmere Polo, Navy Suede
3 pieces, 2 stores, €1054
Cashmere Knitted Polo Shirt in Taupe
Sunspel
€475
Textured Wool Trouser in Truffle
Sunspel
€350
Square-toe suede Chelsea boots
COS
€229
Slate Tee, Espresso Chino
Slate Tee, Espresso Chino
3 pieces, 3 stores, €374
Long Sleeve Classic T-Shirt
Sunspel
€125
Cotton Straight-Leg Chinos
COS
€89
Split Suede Ankle Moc Toe Shoe
Massimo Dutti
€160
Stone Polo, Navy Chino
Stone Polo, Navy Chino
3 pieces, 3 stores, €705
Cotton Basketweave Polo Shirt
Sunspel
€365
Slim-Fit Stretch Trousers
BOSS
€179.95
Split Suede Ankle Boot
Massimo Dutti
€160
Blush Cashmere Polo, Black Slim
Blush Cashmere Polo, Black Slim
3 pieces, 3 stores, €950
Cashmere knitted polo shirt swansdown
Sunspel
€475
Cotton blend slim fit trousers black
Massimo Dutti
€80
Leather Chelsea boots black
Sandro
€395

Shop ankle boots

Edward Brown Suede Chukka Boots
Ulanka
Edward Brown Suede Chukka Boots
€89.99
Split suede moc toe chukka boots
Massimo Dutti
Split suede moc toe chukka boots
€130
Split suede chukka boots
Massimo Dutti
Split suede chukka boots
€130
Split Suede Ankle Moc Toe Shoe
Massimo Dutti
Split Suede Ankle Moc Toe Shoe
€160
Split Suede Ankle Boot
Massimo Dutti
Split Suede Ankle Boot
€160
Suede Chukka Boots
Pollini
Suede Chukka Boots
€174.97
Leather Blucher Ankle Boots
Massimo Dutti
Leather Blucher Ankle Boots
€190
Leather Chelsea Ankle Boots
Massimo Dutti
Leather Chelsea Ankle Boots
€190
Oiled leather Chelsea boots
Massimo Dutti
Oiled leather Chelsea boots
€190
Leather Chelsea Boots
COS
Leather Chelsea Boots
€199
Suede Desert Boots Black
COS
Suede Desert Boots Black
€229
Square-toe leather ankle boots
COS
Square-toe leather ankle boots
€229

How we style ankle boots

Ankle boots carry the outfit when everything around them is quieter. The pairing we come back to is trousers, with polos as the second option. Each look above is complete: open it to see every piece, the total price and where each one is sold.

Brands in this edit: Ulanka, COS, BOSS, Massimo Dutti, Castañer, Pollini, Our Legacy, Doucal's, Church's, Lemaire, Sandro.

Other colours

Brown Ankle Boots for MenBlack Ankle Boots for Men

More style guides

Knitwear for MenTrousers for MenT-Shirts for MenJeans for MenSneakers for MenDerby Shoes for MenLoafers for MenPolos for MenChinos for MenBoots for MenShirts for Men

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