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My first ever pair of Tim's. I gotta say after two days of wearing them it's painful asf on the inside of my ankles. Does it normally hurt to wear them in? :
My first ever pair of Tim's. I gotta say after two days of wearing them it's painful asf on the inside of my ankles. Does it normally hurt to wear them in? :

Timberland 6-inch Basic Waterproof Boot Review
Timberland 6-inch Basic Waterproof Boot Review

Fix Timberland - Boots hurt Ankles Repair (without cutting the leather). - YouTube
Fix Timberland - Boots hurt Ankles Repair (without cutting the leather). - YouTube

How to Break in Timberlands (15 EASY Ways) - Wearably Weird
How to Break in Timberlands (15 EASY Ways) - Wearably Weird

How to Break in Timberlands (15 EASY Ways) - Wearably Weird
How to Break in Timberlands (15 EASY Ways) - Wearably Weird

Mens Timberland 6" Classic Boot - Wheat | Journeys
Mens Timberland 6" Classic Boot - Wheat | Journeys

Timberland PRO Women's 6" Hightower Alloy Safety Toe WP Work Boots - A1KIT214
Timberland PRO Women's 6" Hightower Alloy Safety Toe WP Work Boots - A1KIT214

Wear This, Not That - The Timberland Look Minus the Bunions | Anya's Reviews
Wear This, Not That - The Timberland Look Minus the Bunions | Anya's Reviews

Shop Timberland 6 Inch Premium Vibram Boots TB0A2KKM231 | SNIPES USA
Shop Timberland 6 Inch Premium Vibram Boots TB0A2KKM231 | SNIPES USA

Timberland Women's Kinsley 6-inch Waterproof Boots, Wheat Nubuck, 7.5 : Target
Timberland Women's Kinsley 6-inch Waterproof Boots, Wheat Nubuck, 7.5 : Target

My Boots Rub My Ankles, What Can I Do? — Boyers BootnShoe
My Boots Rub My Ankles, What Can I Do? — Boyers BootnShoe

Amazon.com | Timberland Women's Nellie Double Waterproof Ankle Boot,Wheat Yellow,5 M US | Ankle & Bootie
Amazon.com | Timberland Women's Nellie Double Waterproof Ankle Boot,Wheat Yellow,5 M US | Ankle & Bootie

Timberland PRO 65030 Waterproof 6" 200 Gram Thins
Timberland PRO 65030 Waterproof 6" 200 Gram Thins

Timberland 6" Classic Boot - Big Kid - Wheat | Journeys
Timberland 6" Classic Boot - Big Kid - Wheat | Journeys

Wear This, Not That - The Timberland Look Minus the Bunions | Anya's Reviews
Wear This, Not That - The Timberland Look Minus the Bunions | Anya's Reviews

TIMBERLAND BOOTS CAUSING ANKLE PAIN ISSUE FIXED!! | NYC WEEKEND VLOG - YouTube
TIMBERLAND BOOTS CAUSING ANKLE PAIN ISSUE FIXED!! | NYC WEEKEND VLOG - YouTube

Help] Timberlands hurt my ankle, any suggestions on how to fix it? : r/Boots
Help] Timberlands hurt my ankle, any suggestions on how to fix it? : r/Boots

Wear This, Not That - The Timberland Look Minus the Bunions | Anya's Reviews
Wear This, Not That - The Timberland Look Minus the Bunions | Anya's Reviews

6 Ankle Boots Bring Blissful Comfort to Problem Feet
6 Ankle Boots Bring Blissful Comfort to Problem Feet

Timberland Women's Kinsley 6-inch Waterproof Boots, Black Nubuck, 9 : Target
Timberland Women's Kinsley 6-inch Waterproof Boots, Black Nubuck, 9 : Target

How to Wear Timberland Boots: Tips on Lacing & Styling Timbs | Complex
How to Wear Timberland Boots: Tips on Lacing & Styling Timbs | Complex

1112A214 - Men's Boondock 8-inch Composite Toe Waterproof Work Boot - Great Lakes Work Wear
1112A214 - Men's Boondock 8-inch Composite Toe Waterproof Work Boot - Great Lakes Work Wear

Timberland Premium Waterproof Boot Review - Is the Hype Real? - stridewise.com
Timberland Premium Waterproof Boot Review - Is the Hype Real? - stridewise.com

What Are The Best Timberland Work Boots For Men? – Answered!
What Are The Best Timberland Work Boots For Men? – Answered!

How to Lace Walking Boots for Ankle Pain - YouTube
How to Lace Walking Boots for Ankle Pain - YouTube

Timberland Mid Waterproof Hiking Boots (Review) 2021 - Task & Purpose
Timberland Mid Waterproof Hiking Boots (Review) 2021 - Task & Purpose