Hats for small heads

Q. I’m looking for a cute hat to wear on cold and rainy days that won’t leave me with terrible hat head (i.e. no tight fitting, knit hats). I am looking for a newsboy cap or a fedora-type hat. I know they’re very hot right now and can be found almost everywhere, but my problem is, I have a small head and most hats are too big for me. Even hats that are labeled "small" are too big. I need a hat that won’t blow off on windy days or when I’m riding my bicycle. Can you help me find an adjustable or small size hat?
-Hat Attack

A. I’ve never had your problem – most hats are too tight on my head so I’m always looking for the medium or large size.  And I, too, like them a little loose so I can “try” to avoid hat head.  But if you’re looking to be able to keep that hat on when it’s windy or when you’re riding your bike, you need a hat with a buckle so it’s loose on some days and tighter on others.   Before shopping for a hat, especially online, take measurements of your head so you can find the right circumference or diameter that will fit.  And don’t assume that a knit hat is not right for you, I have a knit newsboy cap that is loose on top, but fits around my forehead so my hair doesn’t get flat.  Also, don’t forget to spray a little hairspray on hair or in the hat to avoid static and loose fly-aways during the dry, crackly months of winter.

Twill Cabbie with Buckle
adjusts for all head sizes
$18 at urbanoutfitters.com


Suede Cabbie with Buckle
adjusts for all head sizes
$19.99 at urbanoutfitters.com


Burberry Wool Bucket Hat
check out their hat size
guide for the right fit
$195 at saks.com


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  1. Kathy
    Jun 24, 2009 @ 12:16:54

    Where can I find a beach hat for a small head? Most are too big for me. The circumference of my head is about 20-21 inches.


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