Ana,The construction and fit between the two models is going to be identical. The difference is in the material of the uppers. The Pull-up has a nice full grain leather with a subtle shine. It will look professional and be is easy to maintain.The oiled is exactly that, an oiled leather. All leathers are naturally hydrophobic (water resistant) when you add oil to the leather it just makes it more so. Dankso describes this as more a rugged ready for the out door type shoe. With the oiled shoe scratches, will appear in a lighter color. These can be rubbed out fairly easy though.Bottom line: oiled would best if you wear khakis or jeans, let's call this the weekend or business casual clog. The Professional Pull-up would be ideal for a skirt or a slack. Please visit http://www.dansko.com/#detail,Professional,Stapled%20Clog,2 for more details and comparisons.Mahalo, Sumo