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The Hill-Side Sneaker Giveaway – Vote For Your Top Choice!

The last month has seen us run a series of contests, awarding one lucky winner with a Freenote Cloth Waxed Riders JacketLeft Field NYC bundle, or Tanner Goods “Worth Holding Onto” Kit. For our latest giveaway, which just closed on Friday night, we teamed up with the good people at The Hill-Side and are looking to hook someone up with a pair of their made-in-Japan Heavyweight Covert Twill sneakers.

Although we had originally planned to simply pick the most beat up, well-worn shoe and call it a day, it turns out doing so was easier said than done. There were just too many strong contenders amongst the dozens of submissions, so we thought why not pick a few of our favorites, then turn to you to help us decide?

Take a look at the five models below and let us know which worn shoe is your top choice by Saturday, November 21st, 5:00PM EST. By casting your vote, you could win an Indigo Pima Cotton Knit Cap, another heavy-duty staple from The Hill-Side!


1. Rising Sun Cadet Boots (1 Year, 8 Months)

Courtesy of Charles D., apart from carpentry work, this pair of rugged Rising Sun Cadet haven’t been worn for any particular activities. Although they have loads of life left in them, they’re already showing beautiful wear; most notably the indigo crocking on the rough out leather.

No longer available.


2. Converse x Comme Des Garçons Play Chuck Taylors (2 Years)

Chucks seemed to be the prevailing sneaker of choice amongst contest entrants, but few achieved the so-dirty-it’s-good look as Michael S. (@_smithstagram on Instagram). By means of biking, concert-going, and even a few hikes, he certainly put his Comme Des Garçons makeups through their paces; so much so that he had to glue parts of the outsole to prevent the shoe from falling apart.

Available for $125.00 from Nordstrom.


3. RRL Denim Espadrille (2 Years)

Courtesy of Salvatore R. (@dirtydenim on Instagram), what was once a special shoe worn only with specific outfits became an all-day-every-day house slipper. Make note of the sashiko stitching near the top, this may well be the first set of toe fades we’ve seen too.

Available for approximately $150.00 from Rakuten.


4. Clarks Desert Boots (4 years, 4 months)

We received quite a few of Clarks Desert Boots, but this pair from Konstantin M. of Vacations-On takes the cake (note: if you’re interested to learn more about footwear soles, read our guide, “Know Your Soles: The 8 Most Common Options“). An everyday shoe for Konstantin, they’ve pounded the pavement of numerous European countries over the years and undergone biannual Nikwax treatments. With the help of Saint Petersburg’s Afour Custom, he recently had the crepe outsole replaced with an eye-catching Vibram Morflex sole.

Available for $130.00 from Nordstrom.


5. Vans Authentic (5 years, 6 months)

From Thomas P. (@verschaald on tumblr) comes another classic sneaker recognizable to many, the Vans Authentic. After a year and half of daily wear as his go-to choice for gigs, festivals, nights on the town, and everything in between, they’re now demoted to dirtier tasks and chores. Besides swapping out the laces for a leather pair–which have patinated nicely–they haven’t been repaired or mended at all. Instead, Thomas opted to replace them with a brand new pair in the same color way, pictured side-by-side above.

Available for $50.00 from Need Supply.


Update: Congratulations Konstantin M. and Jordan T. on winning the Heavyweight Covert Twill sneakers and Indigo Pima Cotton Knit Cap, respectively!