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Menswear style guide

How to Style Ankle Boots for Men

14 complete outfits with ankle boots, put together by MISE. In our looks they are worn most often with trousers, polos, chinos and black trousers. They work best for travel and the weekend. The pieces below go from €130 to €395, from Massimo Dutti, COS, Sandro and Castañer.

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
Brown Knit Polo, Black Slim
Brown Knit Polo, Black Slim
3 pieces, 3 stores, €449
Slim merino wool polo shirt
COS
€79
Slim-fit trousers in four-way stretch fabric
BOSS
€179.95
Oiled leather Chelsea boots
Massimo Dutti
€190
Burgundy Knit Polo, Brown Tweed
Burgundy Knit Polo, Brown Tweed
3 pieces, 2 stores, €1045
Extra-Fine Merino Knitted Polo Shirt in Bakelite
Sunspel
€275
Donegal Tweed Trouser in Dark Brown Melange
Sunspel
€395
Split leather Chelsea boots
Sandro
€375
Black Roll Neck, Flannel Brown
Black Roll Neck, Flannel Brown
3 pieces, 2 stores, €1090
Cashmere Roll Neck Jumper Black
Sunspel
€445
Wool Cashmere Flannel Trouser Light Brown
Sunspel
€395
Leather Chelsea Boots Black
Massimo Dutti
€250
Rust Half Zip, Black Trouser
Rust Half Zip, Black Trouser
3 pieces, 3 stores, €645
Extra-Fine Merino Half Zip Jumper in Chestnut
Sunspel
€295
Delaware Slim-Fit Trousers
BOSS
€159.95
Leather Chelsea Ankle Boots
Massimo Dutti
€190
Chestnut Knit Polo, Charcoal Wool
Chestnut Knit Polo, Charcoal Wool
3 pieces, 3 stores, €844
Extra-Fine Merino Knitted Polo Shirt in Chestnut
Sunspel
€275
Textured Wool Trouser in Dark Charcoal Melange
Sunspel
€370
Leather Chelsea Boots
COS
€199
Breton Stripe, Navy Cord
Breton Stripe, Navy Cord
3 pieces, 3 stores, €485
Long Sleeve Classic T-Shirt Ecru Navy Breton
Sunspel
€125
Slim Fit Corduroy Trousers Navy
Massimo Dutti
€80
Leo Suede Desert Boot Coffee
Castañer
€280
Slate Knit, Navy Cord
Slate Knit, Navy Cord
3 pieces, 2 stores, €754
Extra Fine Merino Crew Neck Jumper
Sunspel
€225
Corduroy Trouser
Sunspel
€330
Leather Chelsea Boots
COS
€199

Shop ankle boots

Split suede chukka boots
Massimo Dutti
Split suede chukka boots
€130
Split suede moc toe chukka boots
Massimo Dutti
Split suede moc toe 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
Oiled leather Chelsea boots
Massimo Dutti
Oiled leather Chelsea boots
€190
Leather Chelsea Ankle Boots
Massimo Dutti
Leather Chelsea Ankle Boots
€190
Leather Chelsea Boots
COS
Leather Chelsea Boots
€199
Suede desert boots black
COS
Suede desert boots black
€229
Square-toe suede Chelsea boots
COS
Square-toe suede Chelsea boots
€229
Leather Chelsea Boots Black
Massimo Dutti
Leather Chelsea Boots Black
€250
Leo Suede Desert Boot Coffee
Castañer
Leo Suede Desert Boot Coffee
€280
Split leather Chelsea boots
Sandro
Split leather Chelsea boots
€375

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: Massimo Dutti, COS, Sandro, Castañer.

Other colours

Black Ankle Boots for Men

More style guides

Trousers for MenT-Shirts for MenJeans for MenLoafers for MenKnitwear for MenDerby Shoes for MenPolos for MenBoots for MenShirts for MenChinos for MenSneakers for Men

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