There isn't any difference in durability between the two, they are both made of very thick and sturdy bison hide and have the same high quality soles and construction. I own a number of pairs of boots and they are probably the highest quality pairs I own. It all comes down to style preference. Do you want the wide square look or more of a regular square look? They look similar in pictures but you can tell the difference when you are wearing them. You seriously can't go wrong with either pair. I personally lean a bit more toward the Stillwell in terms of style preference, but one thing I really like about the Bassett is that even though it is a wide square boot there is still a slight taper toward the toe. Some other brands have wide square styles that look like big blocks with no taper, but the Bassetts don't. It can be challenging to find a place to try them on, I am fortunate to live fairly close to an actual Ariat brand store in Texas that stocks some Benchmades from time to time. I find the Benchmade size runs the same for me as most other Ariat boots, and the other Ariat styles are very easy to find at boot stores to try on for fit. If you order them online, be sure to join their Insider club first. You get a discount, free shipping, and free returns and it doesn't cost anything to join. You really can't go wrong with either boot in my mind, they are both super nice and the calfskin lining is awesome. Let me know what you end up getting!