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Style # 29730
Timberland Men's Windchill Chukka Boot

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Timberland Men's Windchill Chukka

$129.99   price may vary based on color
Walk in the total comfort of the rugged Timberland windchill chukka boots. It features a full-grain waterproof leather upper with a comfortable, padded collar and a rubber lug outsole for superior traction and durability.

  • Waterproof leather upper with rustproof hardware
  • Padded insole
  • Superior traction lug outsole
  • Free returns to over 1100 stores! see details


    Ask a Question asked: Why did you choose this?

    • Barbara: "name brand and durable, gift"
    • Elika: "My honor student son gift, he love it"
    • MIGUEL: "I have been a big fan of Timberland Boot's ever since I wore them in my teen aged years so I've always loved the styling, quality, & durability of their products. Now, I just can't wait to rock them with some nice pair of of jeans!!!"
    • William: "We just ended a bitter winter. These boots were comfortable and warm. The collars are great... they do not cut into my ankles. The foreman of a tree pruning company inquired about them while completing a job on my property."
    • Jean M: "by brand"
    • Jessie: "I like the Timberland brand. I wish there were more types of chukka boots in size 14"
    • Sheri: "Because of the quality and style."
    • Paris: "because these are my favorite please never discontinune!"
    • Humberto: "I liked the look and because of the waterproofing."
    • Kenneth: "Good fit, water resistant, nice looking"
    • Patrick: "original looks great"
    • Margaret: "referred by brother"
    • susan: "b/c my son already has an old pair and wants a new pair. he likes them"
    • Matthew: "I liked the way they looked and felt. Its a very nice shoe"
    • Karen: "my son wanted them"
    • Jolita: "Good price, great quality shoe, size available, quick delivery"
    • Marci: "i have purchased them at your store before."
    • Paula: "My son wanted these shoes"
    • sandra: "Gift for son and plus they are awesome looking"
    • Jennifer: "Timberlands are the best!!"
    • Gail: "for my daughter. looked feminine"
    • beverly: "my grandson liked these boots"
    • Sue: "son likes them"
    • Maria: "Nice gift idea, low boot vs usual high boot"
    • H: "Is a great boot with awesome reviews"
    • anthony: "they look very,very cool"
    • S: "Christmas present"
    • colleen: "christmas gift for my son"
    • Elizabeth: "My son asked for them for Christmas"
    • Deborah: "I had this pair of shoes for the last 5 years and I love them. I am excited they are still being sold because I could not find them in local stores."
    • Bonnie: "son asked for them - timberland brand and 20% off"
    • Laurie: "quality"
    • P: "Only company that had the right size"
    • Pratik: "like it!"
    • Amy: "Present for my honey"
    • Kate: "Great Christmas present for my fiancé!"
    • Timothy: "Sons Request"
    • Karen: "i wanted one for my dad and my brother"
    • Erin: "on sale ;-)"
    • Satyarth: "I never had a pair in this color. I tried this in store and it felt solid and comfortable. They didnt have the right size for me so i ordered online. I realized that their size is different than regular brands. My size is 9 and i could fit in 8 in this one."
    • Carissa: "Husbands loves this brand."
    • Dorothy: "Asked for Xmas gift"
    • Jane: "christmas present for college bound student"
    • Catherine: "Grandson"
    • Claudia: "My boy likes them"
    • Erika: "Timberlands are a long trusted brand and worth every penny!"
    • Deborah: "My son loves these boots. They are comfortable and look great with jeans."
    • Somaly: "My husbands favorite pair of boots..."
    • M: "Style and for gift"
    • Elwin: "have a pair and like them"
    • Laura: "hard to find"
    • Daryl: "This is my 3rd pair in 6 years. They are easily my favorite footwear. Comfort and style is why I buy these boots."
    • ronnie: "cant go wrong with timberlands"
    • N: "Quality at a good price!"
    • Crystal: "not a very good fit, returned"
    • Dennis: "as my birthday gift"
    • Ruth: "Awesome looking Timberland..excellent product..the boot is a little hefty, but it is comfortable to walk in. It fits my foot snugly, but not too tight..good fit."
    • Anthony: "Fit great and I have bought these 5 times previously ."
    • erica: "I bought these for my fiance. He loves them! And they still look brand new just like the day I got them for him!!!"
    • sherrie: "Myself, wanted a pair for years and finally got them!!"
    • Christopher: "I bought the same pair about 2 years ago and have been looking for ever since, durable, comfortable, love Timbs!!"
    • Heidi: "Comfort, durability and fashion"
    • thomas: "i really like timbs i really like this style of boot"
    • Esteban: "really liked them"

    Sydney B asked: Does anyone know if boot sizing is the same as tennis shoe (Nike) sizing? Wondering if I need to get a larger or smaller size than what he wears in Nike's? I know the sizes are different for sneakers v. shoes/boots.

    • Andrew: "To clarify...I wear a 10.5 in Nike or Adidas, and I believe I wore a 10 in these...but the best bet would just be to have someone try them on and see how they scale and then use that to make the purchase...good luck!"
    • Andrew: "I wore them out and got rid of them a few months ago, so I can't guarantee for sure, but I'd like to say they ran about a half size smaller than what I wear in Adidas or Nike."
    • Shavone: "They do run bigger"
    • Jeanie: "I bought these last year, and I bought the same size as his tennis shoes...he love them! They fit perfect! "