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.

April 3, 2018 9:00 am

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


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


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


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


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


The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.