Ever since...

...I was a little girl, I have been a big fan of hats. I love pretty much all kinds of hats, except for wide-brimmed hats, though I think that some people look fantastic them. Fall (and Winter, but we will cross that bridge when we get to it) is one of the greatest time for head-wear (it's like footwear, but for your head). There is the newsboy cap, which though some of the magazines have declared “over” I have just come to appreciate its grandeur. This is yet another fondness that comes courtesy of Ace. Last winter she bought a newsboy cap on clearance, and I scoffed. When I was helping her clean out her closet this summer and happened upon it, I promptly declared that I would be stealing it when I was home on break from school. She didn't like that so much.
Anyway, back to the topic at hand: newsboy caps. The biggest issue when wearing a hat is deciding what to do with your hair and especially your bangs. Here are my suggestions:

--If you have a bob, or hair that ends before your shoulders, wear your hair down and strait. Bangs should be tucked back under the hat; use a bobby pin to pin them back if they are reluctant to stay. If you have side-swept bangs, sweep and hold them to the side as you put on the hat; they should fall forward just a bit (slightly less than they do without the hat).

--If your hair is longer, and you want it back, pull it into a low messy-bun, with a few strands hanging out around your face/hair. Otherwise from the front, it will look like you have pulled a Britney and are covering up your newly shaved head with a hat.

--If you wish to wear your long hair down, wear it wavy or curly if at all possible. Brush and part your hair as you would if you weren't wearing a hat and then place the hat on your head. Try not to tuck hair behind your ears, though you can put that little section that is right in front of them ear behind your ear. If you need a good visual, you can Google “Jessica Simpson in a newsboy cap” to see several pictures The girl may do a lot of looks wrong, but she sure does this one right.

Good luck in your Newsboy endeavor's. Oh, and while we are on the subject of newsboys, you should really rent the Disney movie “Newsies” sometime. It is fabulous, and features many newsboy caps.