The short answer
Choose the Blundstone 500 if you want the leanest expression of the Original series. Pick the 550 for a warmer walnut-brown Classic with leather lining. Choose the Blundstone 585 Chelsea boots for the same comfort-minded Classic construction in the brand’s distinctive rustic brown finish.
All three share the easy pull-on Chelsea profile. The meaningful differences are the leather appearance, the underfoot feel, and how refined you want the interior to be.
The 500: direct and dependable
The Blundstone 500 is the benchmark: brown leather, dark elastic, and an uncomplicated interior. It starts slightly firmer than a Classic and suits anyone who likes a straightforward boot that can become entirely their own through wear.
The 550 and 585: Classic comfort
The Blundstone 550 uses a rich walnut upper, while the 585 arrives in textured rustic brown. Both belong to the Classics family and add a leather lining plus enhanced footbed cushioning. The result is a more finished feel from the first wear.
Rustic leather is intentionally varied, so the 585 looks relaxed and outdoorsy. The smoother 550 reads a little cleaner. Neither is universally better; choose the finish that works with the clothes you already own.
Editor’s quick picks
Field & Form is an independent editorial journal and is not affiliated with Blundstone. Product features can change; confirm current specifications with the manufacturer or an authorized retailer.