Will Thursday Boots Stretch? The answer to the question "Will Thursday Boots stretch?" depends on several factors, including: The specific boot style: Some Thursday Boot styles are designed with a more rigid construction, while others are more flexible. For example, Chelsea boots often have a more flexible construction than work boots.. How much do Thursday's chelseas stretch over time? I tried on a couple of Legend sizes in the NYC store today and am curious what folks' experience has been with how Thursday's chelsea boots (Duke, Legend, and equivalents) stretch and break in over time.
Since you can't try them in stores, getting your Thursday boot sizing right is important, especially given how often they update their fits.. Conclusion Another helpful tip when trying to find the perfect fitting Thursday Boots is to consider the style and material of the boot itself. Different materials, such as leather or suede, may mold to your feet differently over time and require a slight break-in period before feeling completely comfortable.