Take 20% Off Travel Gear & Clothing. Exclusions Apply.

Detail Images

  • Red Wing Heritage - 3/4 Front
  • Red Wing Heritage - Front
  • Red Wing Heritage - Side
  • Red Wing Heritage - Side
  • Red Wing Heritage - Sole
  • Red Wing Heritage - 3/4 Back
  • Red Wing Heritage - Sole
  • Red Wing Heritage - 3/4 Back
  • Red Wing Heritage - Detail
  • Red Wing Heritage - Detail
  • Red Wing Heritage - Sole
  • Red Wing Heritage - Back
  • Red Wing Heritage - Detail
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Copper Rough & Tough Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Red Maple Muleskinner Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Olive Brown Roughneck Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Hawthorne Muleskinner Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Concrete Rough & Tough Leather
  • Red Wing Heritage - 3/4 Front -
  • Red Wing Heritage - Front -
  • Red Wing Heritage - Side -
  • Red Wing Heritage - Side -
  • Red Wing Heritage - Sole -
  • Red Wing Heritage - 3/4 Back -
  • Red Wing Heritage - Sole -
  • Red Wing Heritage - 3/4 Back -
  • Red Wing Heritage - Detail -
  • Red Wing Heritage - Detail -
  • Red Wing Heritage - Sole -
  • Red Wing Heritage - Back -
  • Red Wing Heritage - Detail -

Current Color

  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Copper Rough & Tough Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Red Maple Muleskinner Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Olive Brown Roughneck Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Hawthorne Muleskinner Leather
  • Red Wing Heritage - Weekender Chukka Shoe - Men's - Concrete Rough & Tough Leather

Red Wing Heritage Weekender Chukka Shoe - Men's

$229.95

Free 2-Day shipping on orders over $50. Learn More

Select a Size:

Select options
  • Select options
    • 8.0
    • 8.5
    • 9.0
    • 9.5
    • 10.0
    • 10.5
    • 11.0
    • 11.5
    • 12.0
    • 13.0

    Select a Color:

    Select options
  • Select options
    • Copper Rough & Tough Leather
    • Red Maple Muleskinner Leather
    • Olive Brown Roughneck Leather
    • Hawthorne Muleskinner Leather
    • Concrete Rough & Tough Leather
    4.5513

    13 Reviews

    Details

    Weekender Chukka Shoe

    Whether you're trying your hand at line-dancing at the local country bar or hustling youngsters on the pool table, the Red Wing Heritage Men's Weekender Chukka Shoe commands the attention and respect of any room it enters. The leather upper is the epitome of quality and craftsmanship, while the ComfortForce footbed ensures your dogs won't bark too early on into your night. Rounding this shoe out, a durable and grippy Hill outsole gives your foot just the right moves every time you slip them on.

    • Leather upper
    • ComfortForce footbed
    • Texon Board insole
    • Hill outsole
    • Item #HTG000J

    Tech Specs

    Upper Material
    leather
    Closure
    lace
    Last
    60
    Footbed
    ComfortForce
    Midsole
    Texon Board
    Sole
    Hill
    Recommended Use
    casual
    Manufacturer Warranty
    limited

    Tech Specs

    • Reviews
    • Q & A

    What do you think about this product?

    Have questions about this product?

    Boyfriend is stoked! Size down a half

    • Familiarity: I gave it as a gift but have feedback to share
    • Fit: Runs large

    I heeded other's reviews and purchased 1/2 size down. My boyfriend loves these shoes for everyday casual wear. They are comfortable, are breaking in more every day, and the tread is good and grippy for messy winter walks around town.

    Something went wrong

    • Familiarity: I returned this product before using it
    • Fit: Runs large

    Leather discoloration from the first minute I put boot on
    Very tight
    Smell of leather is overwhelming
    Worst then GI military boots

    Copper Rough & Tough. And it is rough and tough.But does not hold color. Take a look at photos other people had posted. If you take a really hard look you sill scratches and discoloration in several places. And why there is no lining? Such leather requires lining for comfort.

    Yeah so Copper Rough and Tough leather has what's called a "pull up". Which means every time you walk or bend any point of the leather you get distress creases. It's characteristic to our specific leather and ultimately is the reason why it's the #1 leather color we sell. Everyone loves it!

    Now if you look hard at any leather you should see scratches deep in the pigment, it's skin after all. The cattle get bug bites, barb wire scars, etc from just being out in the fields. It's especially apparent on organic free range cattle. They get lots of bites and rub up against barb wire to scratch or to find that coveted piece of grass on the other side of the fence.

    Best chukka on market

      Amazing chukka. Runs large. Size down half to full size. I wear a 10.5-11 in most footwear and a 10 in these was perfect. No break in at all. Out of box felt great. Buy these and you will not be sorry

      Perfect light weight boot

      • Familiarity: I've used it several times
      • Fit: True to size
      • Size Bought: 13
      • Height: 6'2"
      • Weight: 175lbs

      Right out of the box the leather was soft, but it hasnt lost its structure as the shoe has broken in. I dropped in super feet and use them almost daily.

      Quality Shoes

      • Familiarity: I've used it once or twice and have initial impressions
      • Fit: Runs large
      • Size Bought: 9
      • Height: 5'11"
      • Weight: 200lbs

      Was looking for a quality every day shoe that would last for years - think I found them. Great construction & material quality, really nice looking too (got the copper color). They do run a bit big if you ask me, I wear a 10 Nike but ended up with a 9. Would recommend this shoe to a friend.

      Love these shoes

      • Familiarity: I've used it several times
      • Fit: Runs large
      • Size Bought: 8.5
      • Height: 5'9"
      • Weight: 140lbs

      These are my go to shoes for everyday wear and walking to class. Very comfortable once they break in. I usually wear 9.5 but got 8.5 on sale and they're a little snug but stretched out just fine. I've had them several months now and they have no visible signs of wear other than scuffing and tread wear, so they appear very sturdily built.

      Size does matter

      • Familiarity: I've used it once or twice and have initial impressions
      • Fit: Runs large
      • Size Bought: 10
      • Height: 6'
      • Weight: 205lbs

      I ordered these without trying them on due to location. I wear a size 11 sneaker. Everything Ive read about sizing down suggested I get a 1/2 smaller than what I would usually get. I doubled down because I would only be wearing these with dress socks, at size 10 they fit perfectly. Once they break in they're a great shoe.

      Amazing Chukkas

      • Familiarity: I've put it through the wringer

      These shoes look and feel great. Really good shoe for fall and they have a great fit. I sized a half size down and they fit perfectly. I'd suggest getting a leather cleaning kit as well to keep them in good shape. Other than that you really can't beat the style and quality of these Red Wings.

      Classic Style

      • Familiarity: I've used it several times

      They run large. Normally, most shoes I’m a 9, but for this boot Im an 8. This boot will take a break in period, but worth it because of the nice fit that develops and the weathered look you get. I wear these on cooler days. They are durable, the leather is very high quality. The sole is minimal and anti-slip. The insole has some internal padding, which makes them easy to stand around in

      Forest Through the Trees

      Hailing from the banks of the mighty Ohio River, Django fell in love with Kentucky's Red River Gorge by way of rock climbing, however, the climbing didn't end with rocks. He decided sleeping "off the deck" was better than in a tent and with a little help from friends, he constructed a simple platform style treehouse 45 ft off the ground, where he ended up living for the next three years. Years later, his passion for building and being suspended transitioned into his life's work - The Canopy Crew.

      Red Wing Weekender Manufacturing

      Just because the Weekenders are not work boots doesn’t mean they aren’t built to be rugged companions. They’re hand-made right next to all of our other Heritage boots at Plant 2 in Red Wing, Minnesota. And the durable leather for their uppers is sourced from the S.B. Foot Tanning Company just down the road, where we’ve been getting our leather for over a century.

      Great Casual Shoe

      • Fit: Runs large
      • Size Bought: 9.5
      • Height: 6'0"
      • Weight: 165lbs

      I've had these shoes for about a week now and love them. The removable footbed is comfortable despite minimal arch support. An insert can fix that for those that need it. Unlike many red wing boots I've had over the years these boots require no break-in of any kind. They truly felt like I'd had them for years on the first wear. The leather is super soft and needs some protectant for sure. They show wear marks quickly but I like a little character anyway.
      Definitely worth noting is size. I wear a 10-10.5 in most everything. I ordered these in a 9.5 and they're still a slight bit loose. Red Wing recommends going a half size down from your normal size. Please order accordingly. I dont think you'll be disappointed.