the insiders club

  • ⭐ 10% off your first order

  • ⭐ 20% back on every order

  • ⭐

    Free Standard Shipping on all future orders

  • ⭐ Private community access

  • ⭐ Cancel anytime

$1/mo. Billed $12/year.

  • 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, brown leather, elastic panels, pull tabs.
  • True Classic x Timberland Pro Chelsea Boots rear view with branded pull-tabs.
  • True Classic x Timberland Pro Chelsea Boots with elastic panels and 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, brown leather, elastic panels, pull tabs.
  • True Classic x Timberland Pro Chelsea Boots rear view with branded pull-tabs.
  • True Classic x Timberland Pro Chelsea Boots with elastic panels and 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

13 Reviews
$170.00

Transparent Pricing

Your dollars pay for better clothes, not higher unfair markup.

Price Comparison for Singles

$170.00
Total Costs
Fair Markup
$248.00
Total Costs
Unfair Markup
Other Premium Brands

*Traditional retail pricing reflects typical wholesale and unfair markups (often 2x at wholesale and 2x at retail)

Color: Buy 3 Get 1 FREE

Fit: Choose a size.

Size Guide

Size: Choose a size.

Size Guide
Expected delivery 03/14 - 03/19

Complete the Look

Black Heavyweight Long Sleeve Pocket Crew

Heavyweight Long Sleeve Pocket Crew

Color: Black

$44.99 $22.50
Medium Indigo Wash Straight Authentic Denim Jeans

Straight Low-Stretch Jeans

Color: Medium Indigo Wash

$69.99 $49.99 Clearance

This item is FINAL SALE and is not eligible for additional discounts, exchanges, or refunds

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.

You May Also Like

Customer Reviews
View full details
Home
Shop
Credit
App
0
Cart