May I ask how deep is this cap ? I have a big head, the circumference of this octagonal hat fits me. I'm afraid it won't hold my head

it's a real blend wool flat cap type of cap, it is difficult to measure the exact height of the crown, it depends on your head, I think if the size fits, I think it also can also hold your head. if you like a cloth cap than can be worn with a suit or jeans, kind of an all around herringbone cap, If you prefer a cloth hat to a suit or jeans, then you will like this.

I'm looking for a looser/baggy style without a snap on the bill. Does this have that snap?

No snap. Also, not baggy style. I love my cap, it's just st what I wanted. I know what you're looking for and this one isn't it.

Do this gatsby hat suit for a man who is over 50 years old???

Really, I bought this newsboy cap as a gift for my dad who is 59 year old, looks handsome, but I think this octagonal cap is suitable for a lot of ages. I want to buy one more for my 25-year-old nephew, too. really recommend this!!

What measurement is large

You'd just have to look at the chart and go by that. I wear a small to medium in most of my hats but, it may vary in each individual.

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