The headsize ribbon helps the hat keep its size and keep clean (by absorbing sweat — yum, I know). To get it to lie flat as it circles inside the crown, you have to iron the grosgrain ribbon while gently curving it, a process called swirling.
And, finally, I thought to take some pictures of the process at the last minute, at home one night as I finished up on my own. I have the headsize ribbon pinned in place. Pinning is tricky in itself, because the ribbon needs to lie flat against the brim without pulling it tightly, or else the size might be too small (not a good idea for me, although it is an option if you have a hat that's a tad too big).
Here I'm sewing it along just the edge nearest the opening of the brim.
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