I'll mention right away that I did not buy these for any type of work related purposes. I was just looking for a good black leather boot with a round toe and completely flat sole that I could wear every day. The fact that these are made to be tough and waterproof is just a bonus for me. I'll be able to walk through Wisconsin streets in winter without worrying about cold, wet feet or shoe damage, yet can also wear these at any other time because they just look cool. I've had them for a couple weeks now and feel they didn't need much breaking in. Since they're a fabric lined leather boot, that helps things along. I appreciate that there's padding around the ankle yet it doesn't buldge out oddly. I feel the boots have great grip on all the surfaces I've been on, whether it be tile floors, concrete or metal slabs on bridges. The boots offer good stability for me as I walk also. I'd say the fit is true to size. I'm a woman and wear size 11, which is 9.5 in men's. They fit perfectly with the appropriate amount of space at the toe. My feet are maybe slightly wider than average although not wide enough to require wide sizes in casual, non-dress shoes like sneakers. These boots have the perfect amount of room in them. That comes in handy as I've swapped the brand's insole for a different one. That's probably the only thing I'd suggest the brand change about this boot. They include a memory foam insert but for me it's not dense enough to really absorb shock. I wore them with the included insoles for two days but felt the lack of support and shock absorbtion all through my legs and feet. (Of course this could just be my body specifically, but I'm only 33 years old so it might feel worse if you're older or have back,feet, etc issues.) I ended up putting in different inserts with denser foam and arch support and now my boots are perfect. But if you have wide feet and need to put different insoles that take up room in shoes, these might end up a little tight on you.