CastratedWeasel: You could start from a cylinder grab the top face then delete most of it to just be left with the top part then drag the edges down to create a oval then just make the indents as you normally would. Or just start with a plane and move some verts around.
(I'm hiding the top because I didn't manage the edges properly) Basically you just want to start with a sphere with a lot of divisions, I started with 128 edges, ended up with 192, but it looks like you'll want a bit more than that to exactly match the concept.
Start with a quadsphere bro. Max unfortunately does not have it as a standard primitive so you have to make it by starting with a 6 faced cube then add these modifiers: meshsmooth spheriphy meshsmooth spheriphy make sure to top it off with no less than two Edit Poly modifiers to be sure though.
Cloth isn't really mechanical/hard-surface stuff that this thread focuses on. Clothing is mostly ZBrush work. One way to do it is to start out with a base mesh that conforms to your character body and then start modeling the larger shape-changing details such as collars, tucked waists and rolled-up sleeves etc. Once that…