The upper of Timberlands is made of 100% leather that is initially stiffer and needs a break-in period to stretch and adjust to feet shape. To make them comfortable, wear the shoes and treat them in the same way as you would do while hiking, working, or walking. This helps them to loosen up and fit your size. The way you are breaking in your Timberland shoes will determine their fit and comfort for the entire lifespan. I will also suggest you walk around the backyard of your house by wearing Timberland boots so that you can properly determine their fit. Another step that you can do for stretching the Timberland shoes is to hold them in hand and bend the soles back and forth repeatedly to speed up the process.