Here's another post with advice on what sorts of hats suit which face shapes. I'm still looking for one that takes into account that you might want to put your hair up in the hat, but in the meantime, this is still helpful, I think. However, I'd have to actually figure out my face shape in order to understand the advice. I've read the descriptions and they always baffle me a bit.
And another perspective on adjusting to covering your head or hair. Melissa's very intentional gradual transition connected to me to my own experience of engagement very strongly. Here I was, "off the market" and yet not yet married, and feeling like it was an appropriate time to start playing with the equivalent of an engagement ring on my head. Of course, I already covered partially, for other reasons, but already at that point, it made me start thinking of my caps and headbands as double-purpose coverings. It also meant that I already had lots of practice in thinking about how to get scarves to stay on my head by the time I got married.
Here's a personal reflection about hair covering through the course of a marriage, divorce and up-coming remarriage. It isn't something I've really touched on, in this blog, and I really appreciated the perspective. I think you will too. Here's the same author's thoughts shortly after her divorce. A lot of attention around women's head covering gets put into newlyweds and engaged women contemplating this practice. Very little that I've seen goes into talking about divorce, loss and other changes that are less pleasant and exciting. But that's part of a full and authentic look at any religious practice- how does it interface with the whole life? I'm grateful for these posts opening up that door for me to look inside.