The Best Deal You’ll Ever Get on Footwear That’ll Last a Lifetime

Oak Street rarely puts on a sale this big. So act fast.

The Best Deal You’ll Ever Get on Footwear That’ll Last a Lifetime

The Best Deal You’ll Ever Get on Footwear That’ll Last a Lifetime

By Michael Nolledo

If you’ve long been a follower of InsideHook Chicago, you should know our fondness for Chicago-bred company Oak Street Bootmakers — not only because we love to root for the home team, but because the brand makes some of the most rugged, gentlemanly US-built footwear around. 

By timeless standards, they’re an easy brand to love. The label is responsible for your correspondent’s most beloved boots, which are dependable, easy to style and carry a certain heft and quality that begs to be tested, not cradled. That’s thanks to impeccable construction and sourcing of the best materials in the world, Chicago’s own Horween Leather Company among them.

Being followers for some time, we can tell you that its of rare instance that Oak Street decides to slash prices, which makes its End of Season sale all the more special.

Up now on the site, you’ll find a collection of Oak Street’s handmade shoes and boots marked down up to 60%. You’ll find some of our favorites below. 

Black Double Sole Wingtip
A “working man’s” wingtip that’s comfortable enough to be your new daily go-to. $462 $323.40

BUY IT HERE

Tobacco Stampede Marine Field Shoe
A military-inspired field boot with handsomely speckled Vibram Nitrile Cork soles. $462 $277.20

BUY IT HERE

Navy Beefroll Penny Loafer
A loafer with hand-stitched moccasin construction and buttery navy Horween Chromexcel leather. $328 $262.40

BUY IT HERE

Snuff Suede Lakeshore Boot
Every man needs a little bit of suede every now and then, and these snuff suede numbers fit the bill. $498 $373.50

BUY IT HERE

Bourbon Calfskin Campus Chukka
A clean chukka boot that can be dressed up or down. $462 $346.50

BUY IT HERE

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