• True Classic x Timberland Pro Chelsea Boots, brown leather, elastic panels, pull-tabs.
  • True Classic x Timberland Pro Chelsea Boots with black elastic panels.
  • True Classic x Timberland Pro Chelsea Boots with safety toe features.
  • True Classic x Timberland Pro Chelsea Boots, brown leather, elastic panels, pull tabs.
  • True Classic x Timberland Pro Chelsea Boots rear view with branded pull-tabs.
  • Timberland PRO Chelsea Boot outsole, labeled oil & slip resistant.
  • Man wearing True Classic x Timberland Pro Chelsea Boots, smiling against gray background.
  • True Classic x Timberland Pro Chelsea Boots fabric pull-tab with logo.
  • True Classic x Timberland Pro Chelsea Boots, brown leather, elastic panels, pull-tabs.
  • True Classic x Timberland Pro Chelsea Boots with black elastic panels.
  • True Classic x Timberland Pro Chelsea Boots with safety toe features.
  • True Classic x Timberland Pro Chelsea Boots, brown leather, elastic panels, pull tabs.
  • True Classic x Timberland Pro Chelsea Boots rear view with branded pull-tabs.
  • Timberland PRO Chelsea Boot outsole, labeled oil & slip resistant.
  • Man wearing True Classic x Timberland Pro Chelsea Boots, smiling against gray background.
  • True Classic x Timberland Pro Chelsea Boots fabric pull-tab with logo.

True Classic x Timberland Pro Chelsea Boots

15 Reviews

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$170
$136 20% OFF with JULY20

Back-in-stock email plus occasional news and offers.

Expected delivery 07/03 - 07/08

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Length Comparison

Why you'll love it

Built Tough. Worn Anywhere.

A modern take on Timberland’s workwear legacy—crafted from waterproof leather with an Anti-Fatigue footbed and lightweight all-weather sole. No laces, no break-in, no compromise.

All-Day Comfort
Anti-Fatigue footbed delivers lasting cushioning and support.

Tough Outside, Soft Inside
Durable TPU outsole and breathable ReBOTL™ lining keep you steady and cool.

Find Your Fit
Wide and Regular fits available. Runs large—size down for the best fit.

All-Day Comfort
Anti-Fatigue footbed delivers lasting cushioning and support.

Tough Outside, Soft Inside
Durable TPU outsole and breathable ReBOTL™ lining keep you steady and cool.

Find Your Fit
Wide and Regular fits available. Runs large—size down for the best fit.

Premium & Purposeful
Crafted from waterproof 100% leather for strength, durability, and timeless style.

Built for Every Element
TPU outsole delivers traction and flexibility across all conditions—rain or shine.

Care Made Simple
Wipe clean with a damp cloth to keep them looking sharp.

Premium & Purposeful
Crafted from waterproof 100% leather for strength, durability, and timeless style.

Built for Every Element
TPU outsole delivers traction and flexibility across all conditions—rain or shine.

Care Made Simple
Wipe clean with a damp cloth to keep them looking sharp.

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