This isn't my first pair of El Naturalistas so I may be a bit biased.  These boots were really comfortable the first time I put them on and I don't anticipate having to spend time "breaking them in". I ordered up a size - I wear a women's US size 10 and an EU 41 but ordered these in a EU 42 and they're roomy enough to wear thick socks and then walk miles without worrying about them feeling tight. Being able to put thick socks on also means they're great for winter (in the Pacific Northwest) and the rubber soles are nice and grippy. Overall I think they're very stylish and versatile while being comfortable and providing some ankle support.  Added to this the fact that the company uses earth-friendly vegetable dyes, and recycled and recyclable components wherever they can, I am very happy with my purchase!