Superb shoe, my first chukkas and I'm glad it worked out well with these! I have no arches so have to use inserts, which limits which shoes I can get and all - so as for arch support in these I cannot say, since I have to swap out the standard ones for mine. Other than that though, good shoes and they fit well. I followed suggestions made by others and got a 1/2 size down from my usual, though with shoes it's always hard to tell if I am a 9 or 9.5. The 9 is perfect though, just a bit of wiggle room left so when thick-sock weather rolls around it should be just a tad more snug.<br /><br />We'll see how they hold up, but for the price paid I think there's an expectation of some longevity.