My hat

   A month or so ago I asked Audi of Fashion For Nerds for help in figuring out how to wear a hat because as seen here, she is a hat expert.  Its taken a while for me to send her an email with pictures of the hat, but I finally got around to it.  Audi very kindly allowed me to use her answer in a blog post.  So if you too need help in figuring out how to wear a hat, read her answer to my questions as well as her guest post at Already Pretty.  Here is my email asking for help and hers with her advice. 

Audi,
Thanks so much for offering to find ways to help me wear this hat.  It is 100% wool (or so the tag claims).  I bought it at a consignment store a few months ago and have only worn it twice, both times to walk my puppy Bella.  I would really like to wear it more often, but I just don't know how to incorporate a hat into an outfit or daily wardrobe.  Then there's the question of whether I should take it off when inside or in class or what.  Plus, the hat fits on my head just fine, but I have to wear my hair down or in a super low pony tail in order for it to fit as a normal pony tail, bun or french twist suddenly makes my head too big.  So then I have to think about hat hair.  You're the only person I can think of that can help me with this.   Help me obi-wan, you're my only hope!

Audi's answer:

Haha, I will do my best! That's a cute little hat; you really shouldn't have any trouble pairing it with just about anything because of the neutral color and simple trimming. It would look great with a skirt, blazer, and boots, particularly with an outfit in which you mix different neutrals together. The light gray would pair well with rich browns, black, and darker grays. I also think it'd look great with dark purples and blues. Because the hat is sort of a cross between a fedora and a cloche, you could take in in different directions: a menswear-inspired combo of dress pants, jacket, and button-down (I'm thinking sort of an Annie Hall type of look), or perhaps paired with a floral dress, chunky scarf, and boots.

As far as the hat head issue goes, you have two options: throw the hat on just before you leave the house and use it only as an outerwear component (which means you only wear it outside and not for long enough for the hat head to set in), or else incorporate it into the outfit and leave it on all day. I suppose you could also wear your hair in a low ponytail and then when you take the hat off, pull your hair back into a regular ponytail or put it up in a bun. Dampening your hair and scrunching it, or carrying some sort of volumizing spritzer with you will also help to release the dent left by a hat. That might involve more work than you want to deal with though. If you do want to take your hat off during the day, make sure it is fully dry (and cooled down if you've used a hairdryer) before you put the hat on.

What do you do when you're not sure how to wear something?  Do you do like Tania of What Would a Nerd Wear and try different things and ask for help or just give up or play it safe and stay within your comfort zone?