I have custom orthotics and have SUCH a hard time finding shoes that fit - it's difficult with no orthotics, but add orthotics and ew boy. I have an elevated metatarsal that caused arthritis, bursitis, and a neuroma in my right foot. And I am young and have pretty normal-looking feet, so don't think I have some super-crazy stuff going. But I list all that to convey that I just cannot deal with shoes that don't fit/rub blisters in the heel or that pinch or compress in the forefoot, esp since my feet are so compressible. And I hate when it's loose in the heel but snug in the front - unbalanced and uncomfortable. I find Drew consistently true to size - I dont have any other closed-toe shoes in my actual size - I usually have to size up, between toes that are square-ish (3 same length) and that dang orthotic. I measure at just under a 9 on a braddock device. I got these in 9W. My foot isn't super wide, but I do have a high instep/arch, and my inserts take up a lot of room. I can wear my 3/4 orthotics and a thick sock with these and still have plenty of depth/volume without feeling that one part is loose but another is tight. That means that I can wear them for more than just a couple hours. I don't have many shoes I can wear for more than a few hours without really being in pain. My foot still aches, but at least I can manage with these - today, I wore them for 8 hours, which is just absolutely delightful. Especially since I live in an urban and get around by foot. My only complaint is that Drew uppers seem to sometimes be where they skimp - maybe a little stiff or cheap-looking in some instances. And of course these have an actual shank, which is amazing and shockingly uncommon, at least for a shoe that will take an orthotic. I didn't need the second zipper, but it's a good idea, doesn't get in the way, and I can see that it would be very helpful for some people. It's a very cute boot, and I can wear it in somewhat wet weather. It looks fashionable and my age. So very happy about these boots!