Win it: The Made in Italy Astorflex Chukka

Astorflex Chukka in Dark Chestnut, Dark Khaki, or Whiskey – $145

Note: If you’re a first time customer to Huckberry, use the code DAPPERED20 which is good for 20% off almost entirely site wide (there are a few exclusions here & there). That drops these boots to $116.00. Code expires 4/30/16. Sold only in US whole sizes, they suggest sizing down if you’re in between. If the winner’s size isn’t available, Huckberry will provide the winner store credit in the amount of the Chukka’s price instead.

The obvious question that many are gonna ask will be: “Why not just get a pair of Clark’s instead?” Sure, Clark’s are cheaper. And they’re legendary. But if you’re the type who doesn’t mind paying just a little more for something made just a bit better from more impressive materials, then the Astorflex is going to be worth a good long look.

Traditional shape. Handstitched construction. Built well. Nice & comfortable.

Made in Italy from responsibly sourced materials, these things honestly do look, feel, and wear just that much better than the good ol’ Clark’s DB. They even smell great, right out of the box.

They’re certainly more structured feeling than the Clark’s DB. But make no mistake, it’s still a softer style desert boot. These are not in the same category as the Loake Kempton.

Made with an emphasis on being eco-friendly. Terrific materials both inside and out.

The exterior suede is nice and soft with a good nap that shows shade distinctions when you run your hands across it. The interior is lined in a buttery leather that hugs your feet. You could wear these barefoot if you wanted. (Not sure why you’d want to, but, you could.) The soles are a brownish latex crepe that won’t show dirt and grime anywhere near as easily as the original Clark’s DB does. And while it’s a small detail, the laces that these come with are nice and sturdy feeling. Clark’s laces can feel like you could tear em’ in half if you pulled hard enough.

Sizing feels pretty true. Maybe a tiny bit on the large side. A size 10 fit my 10.5 feet just fine right out of the box, and they’re sold only in US whole sizes. The stamp on the tongue says these are a size 43 in Euro sizing.

Italian made but traditional, casual boot silhouette. Not overly pointy or slim.

They might be Italian, but the toes on these things are not sleek. This is a traditional, rounded boot toe. One that’ll work best casually with jeans or more rugged looking chinos. The welt is hand-stitched, and feels nice and flexible right from the start. So you’ll have some durability but not any stiffness fighting back when you first lace them up.

Plenty of guys will stick to their Clark’s. And that’s completely understandable, being that you can get a pair of dark brown sueded Clark’s DBs for half the price. But if you’re the type to invest a little bit more in something that stands out from the rest, even subtly, in terms of style and quality? Then these Astorflex chukkas could be a go-to casual companion for many, many years to come.

Enter here to win a pair of Astorflex Chukkas from Huckberry. One entry per person. Deadline for entry is 12:59 PM ET on 4/13/16. Again, if the winner’s size isn’t available, Huckberry will provide a gift card/store credit instead. Good luck!

Update: Congrats to J. Draffkorn who won the drawing for the chukkas!