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Chukka Boots

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Sartorial Picks

Chukka Boots

The chukka boot sits in a slightly more relaxed territory than a Chelsea or ankle boot and it's that relaxed quality that makes it particularly useful for casual and smart casual dressing. It has two or three eyelets rather than the full lacing of a derby and that detail somehow makes it feel less formal in a way that's hard to explain but easy to see. We love chukkas in suede specifically because the material adds to that casual ease and the way suede wears and ages gives them a character that leather chukkas don't quite replicate. A tan or sand suede chukka with chinos and a simple knit is one of those combinations that looks like you know what you're doing without requiring any particular effort. They also work well with darker casual trousers when you want something a bit smarter than trainers but not as formal as a proper boot.

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  • 50 products Showing 16–30 of 50 results

  • Dr. Martens Brookline Chukka Boots in Black
    Buy from Schuh

    Dr. Martens Brookline Chukka Boots in Black

    $130.00
  • Dune London Men’s Minato Chukka Boots – Brown20%
    Buy from Sports Direct

    Dune London Men’s Minato Chukka Boots – Brown

    $119.00 Original price was: $119.00.$95.00Current price is: $95.00.
  • Farah Norland Chukka Boot – Brown69%
    Buy from Sports Direct

    Farah Norland Chukka Boot – Brown

    $69.99 Original price was: $69.99.$22.00Current price is: $22.00.
  • Firetrap Chukka Boots Mens – Beige70%
    Buy from Sports Direct

    Firetrap Chukka Boots Mens – Beige

    $99.99 Original price was: $99.99.$30.00Current price is: $30.00.
  • Grenson Chester, Men’s Chukka Boots, Brown Suede, Cigar Size: UK 10.5
    Buy from Grenson

    Grenson Chester, Men’s Chukka Boots, Brown Suede, Cigar Size: UK 10.5

    $325.00
  • Grenson Clement, Men’s Chukka Boots, Peat Suede Size: UK 6.5
    Buy from Grenson

    Grenson Clement, Men’s Chukka Boots, Peat Suede Size: UK 6.5

    $335.00
  • Grenson Keats, Men’s Chukka Boots, Toffee Suede Size: UK 12
    Buy from Grenson

    Grenson Keats, Men’s Chukka Boots, Toffee Suede Size: UK 12

    $190.00
  • Grenson Roman, Men’s Handsewn Leather Moccassin Chukka Boot, Waxy Brown Size: UK 9.5
    Buy from Grenson

    Grenson Roman, Men’s Handsewn Leather Moccassin Chukka Boot, Waxy Brown Size: UK 9.5

    $195.00
  • JEFFERY WEST Men’s Chukka Boots – Black29%
    Buy from Flannels

    JEFFERY WEST Men’s Chukka Boots – Black

    $280.00 Original price was: $280.00.$199.00Current price is: $199.00.
  • John Varvatos Men’s Varick Chukka Boots
    Buy from Bloomingdale's

    John Varvatos Men’s Varick Chukka Boots

    $308.20
  • Nicholas Deakins Chukka Boots – Brown50%
    Buy from Sports Direct

    Nicholas Deakins Chukka Boots – Brown

    $59.99 Original price was: $59.99.$30.00Current price is: $30.00.
  • Off The Hook ‘iggy leather chukka boots ankle moccasin mens boots in brown
    Buy from ASOS

    Off The Hook ‘iggy leather chukka boots ankle moccasin mens boots in brown

    $39.99
  • Off The Hook ‘sahara’ suede leather casual lace-up chukka boots in universe-Blue
    Buy from ASOS

    Off The Hook ‘sahara’ suede leather casual lace-up chukka boots in universe-Blue

    $39.99
  • OFF THE HOOK ‘SAHARA’ Suede Leather Casual Lace-up Chukka Boots-Grey
    Buy from ASOS

    OFF THE HOOK ‘SAHARA’ Suede Leather Casual Lace-up Chukka Boots-Grey

    $39.99
  • Off The Hook Jethro leather casual lace-up chukka boots in dark brown
    Buy from ASOS

    Off The Hook Jethro leather casual lace-up chukka boots in dark brown

    $44.99
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