I normally wear a 9 so I sized up to a 9. I am picky about headsets and headphones. I never had to "break" them in out of the box and bam just put on and off to work for a 10 hour shift its great that my feet,legs, and back no longer ache. I wear it around the house, instead of my bedroom slippers. Her I am all dolled up and my BRAND new shoe broke off! If it helps; I am 53, weighted 200lbs, and wear 40D. It may not be as "cute" as the typical straw beach hat, but theres way more pros than cons to this hat. Maybe change the ear padding? Havent changed it out yet. I didn?t know how to wear it but I saw another girl with tied pearls in a knot so I copied! Is just perfect!