16 Pairs Of Boots/Chukkas For Bros That Are Stylish AF And Perfect For The Fall/Winter

It might still be warm wherever it is you live in America. With this warm weather it’s hard to imagine that in the next several weeks the temperatures will begin to plunge, days are going to get noticeably shorter, the leaves will be changing, and before you know it we’re going to get out first snow of the year. Fall/Autumn is knocking on our door and after that comes Winter, so NOW is the time so start thinking about your cooler weather footwear because the prices will go up in the near future (or if you’re looking for LL Bean’s Bean Boots they’ll be sold out). Below I’ve gathered together 17 pairs of boots and chukkas for you bros, all of them are stylish and will fit with about 85% of your every day wardrobe. I’ve included boots and chukkas of every style and price range because I prefer to be presented with all the best options when making a decision on shoes instead of being forced to choose from just a select few, and hopefully you bros will find a badass pair of boots below that will help you get through the next few seasons!

 

Men’s Bean Boots by L.L.Bean®, 6″ ($109)

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L.L. Bean Men’s Rugged Ridge Pull-On Leather Boots ($89)

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Oliberté Men’s Gando ($150)

  • Premium cow leather upper (Colour may vary due to natural properties)
  • 100% goat leather lining
  • Natural jagged outsole
  • Made in Ethiopia and Fair Trade Certified™
  • Fits ½ to 1 full size big (recommend sizing down)
  • Leather ages with wear
  • Vegetable tanned leather midsole
  • Natural jagged outsole
  • Men’s 6-inch combat boot
  • Traditional stitch-down around base
  • Water-based PU comfort insole with heel stabilizer
  • Flat cotton wax laces

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Oliberté Men’s Mogado Chukka ($140)

  • Premium natural leather upper (colour may vary due to natural properties)
  • 100% goat leather lining
  • Natural Rubber Wedge Outsole
  • Made in Ethiopia
  • Fair Trade Certified™
  • Fits true to size. Longer in the toe, but narrow at the width
  • Traditional stitch-down around base
  • Handstitched at front and back
  • Water-based PU comfort insole with heel stabilizer
  • Poly-cotton blend cord laces
  • Longer in the toe, but narrow at the width

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Sperry Top-Sider Dockyard Oxford Chukka ($84.99, Usually $140)

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Bass Hendrix Chukka For Men ($39, Usually $79)

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John Varvatos Mick Espradrile Chukka ($139, Usually $278)

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Clarks Desert Boot Men’s Chukka ($104, Usually $130)

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Men’s Bean Boots by L.L.Bean, 8″ Thinsulate ($139)

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Rubber Moccasin Men’s Bean Boots ($89)

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UGG Hulman Perforated Men’s Chukka ($89, Usually $150)

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Timberland Britton Hill Chukka ($127, Usually $160)

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Calvin Klein Price Men’s Chukka ($64.99, Usually $130)

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Levi’s® Shoes Banks UL ($34, Usually $50)

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Oliberté Men’s Ngola Chukka ($160)

  • Premium cow leather upper (Colour may vary due to natural properties)
  • 100% goat leather lining
  • Fits ½ to 1 full size big (recommend sizing down). Wider in width.
  • Made in Ethiopia and Fair Trade Certified™
  • Men’s 6-inch combat boot with double toe cap
  • Natural jagged outsole
  • Traditional stitch-down around base
  • This style is built on our GANDO last

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Oliberté Men’s Adibo Chukka Boot ($120)

  • Premium cow leather upper (colour may vary due to natural properties)
  • 100% goat leather dark brown lining
  • Natural rubber outsole with wedge
  • Fair Trade Certified™.  Made in Ethiopia
  • True to size. Narrow at the width
  • Traditional stitch-down stitching around base
  • Water-based PU comfort insole with heel stabilizer
  • Vegetable tanned leather midsole
  • Poly-blend laces
  • Leather ages with wear
  • Men’s 3-hole chukka boot
  • This style is built on our Adibo last

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Ball and Buck x New Balance 585 Sporting Gentleman ($238)

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The BroBible team writes about gear that we think you want. Occasionally, we write about items that are a part of one of our affiliate partnerships and we may get a percentage of the revenue from sales.

Cass Anderson BroBible headshot and avatar
Cass Anderson is the Editor-in-Chief of BroBible. Based out of Florida, he covers an array of topics including NFL, Pop Culture, Fishing News, and the Outdoors.