Dilemmas: Hat Quest

I'm going through a hat envy phase. I like them, but I'm scared of choosing one. Hats seem to thematize your whole outfit, whether it's a fedora, newsboy, beret, etc. But on paper, hats are great for me: I have a hatty head, I burn on cloudy days, and I fiddle with/break other accessories like rings and necklaces.

So I've been casually looking at some hats that I think I would actually wear. Most of the hats I like are close to the head, cloche style, but I'm open to any style, so long as I don't look like I'm 65 years old (or 3 years old). (Or Indiana Jones, or a dominatrix, or Al Capone...)

I'm also open to alternatives: feathery headbands? I don't know. Help me out here.

Banana Republic straw cloche in cream: $30
Urban Outfitters straw bow cloche in brown: $34
Village Hat Shop belted cloche in white: $17
Village Hat Shop sur la tete Monaco sunhat in white: $23
Anthropologie The Brightest Hour hat: $24
Hats in the Belfry braided contour cloche: $44

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9 responses
I like #2 and #4 on you. I also like the idea of feathery headbands and headpieces... I have been meaning to post on these: http://store.bambako.com/products
— Stephanie Lim
Oh dude, I love those, thanks.
— Jena
ooh, i like #1 and #2. There is a fantastic hat store in seattle if you're ever up there...Bernie Utz hats. I got a great fedora there for around ~$30.
— Sushmita
In all seriousness though - what kinds of occasions merit hats?  I can't think of any.  I own two hats (one red cloche from Forever 21 and one paperboy-style houndstooth one).  But I never wear them!
— Stephanie Lim
I agree, I have one hat a lilac cotton one I wear at the beach and only keep the sun off my face. Hate what a hat does to my hair!
— Suzanne
Thanks for the tip on Bernie Utz. I grudgingly admit I have a pale blue fedora and a khaki newsboy Kangol-type cap I never, ever wear (except after three beers).
— Jena
yeah agreed that a fedora isn't an everyday hat - but the night after I bought mine, we happened to go to a party in an art gallery, so my fedora fit in well with a black&white dress. i wear my newsboy-type hat around the city to keep the sun off my face.
i like this one from urban outfitters: http://tinyurl.com/c7kmf3
— Sushmita
um i LOVE IT.
— Stephanie Lim
you definitely have to be confident when wearing hats. they instantly attract everyone's attention upon entering. i like cloche/closer to the head styles too. it looks so lady-like, a la angelina in changeling http://bit.ly/pKyS7
— Maggie Cheung
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