Club Obi Wan

I have yet to get a hat, but one thing that has been worrying me is the measuring. See, I'm one of those people who's hair is never really consistent. Sometimes it's longer, sometimes it's shorter. So will that play an important role in sizing for a hat? Or will it not really matter that much?

I would suggest allowing room for your hair at its longest. If you get it cut, you can always put paper or something inside the sweatband to make up the size, but if you start small you'll have to stretch it.

Also, I wouldn't rely on a tape measure. If you have access to a hat shop, grab several different brands and find out what your real size is before committing to a purchase.

I'm having a tough time figuring out what size I should order for my Fed IV

I like hats to be a little loose, not too loose but not tight at all, not constricting at all. I also know they tend to shrink and I also let my hair grow out more often than not.

Right now (Cut my hair two weeks ago with a #3 on the back blended upwards)
I measure, when the tape is firm/taught (but not tight) I measure 59 exactly.
When I relaxed it a little bit and let my hair puff it out (so the tape isn't pressing the hair), I'm a little over 60.

So what should I order?

Doh wrote:Also, I wouldn't rely on a tape measure. If you have access to a hat shop, grab several different brands and find out what your real size is before committing to a purchase.

Doh- I agree with the idea that it isn't really simple using the tapes. On the other hand trying on hats may be as confusing as helpful. My own case-
Stetson cowboy hats- 7 1/2 or so (standard oval)
Resistol cowboy hats 7 3/8 long oval
Akubra Fed, Banjo (Fawn and Gray), Adventurer 59cm
Art Fawcett 59.5 long oval - and that's the one that's correct! But, see above, only one hat that "fit" was that size. His conformer said 60, btw, and my first tape measurements said 59.1. I was pulling the tape too tight. SOOOOOOOOOooooooooo. . .

Doh is correct you should go to a hat shop if possible. But, they will, likely measure you with a tape. That's just a starting point. If you are crossing brand boundaries the more you know the better.