After reading Jennifer Stoddart's 'dorable Debbie Gibson story and then Nubby's What I Wore post, both in today's feed reader, my mind instantly starting going into trend-obsess mode.  The same impulse that makes me text my boyfriend on the hour every hour to make sure he brings me home this seaon's trendiest purple nail polish is now driving me to scour the web for the perfect quality yet affordable bowler hat.  The look can lean towards fedora or full-on Charlie Chaplin.... Read on for my fave ways to wear.

The O.C. girl Mischa Barton tries out a fedora with a Chaplin twist; Rachel Bilson plays androgynous with a button collar and bowler hat.

A bowler hat looks kind of like a fedora, but is more rounded and generally has a popped-up brim.  The bowler was originally made with a narrow brim and hard bowl piece to protect the heads of horseback riders.  In the U.S. it was called the derby, pronounced dar-bee.

How to wear it...

With Your Goth Garb

Paris Hilton works the bowler hat trend here.  Notice other fall 2008 trends: Leather jacket, the color purple, and her tights. (It is her on the right - she's in a wig!)

The bowler hat is reminscent of Charlie Chaplin, and the goth trend is largely based on Victorian style and vampire novels, so take it there with edgy attire head to toe.  The hat gives a playful twist to a serious black look.  If the hat is too boyish for you, stick a flower in the brim.

With Your Hipster Ensemble

It's hard to see the hat, but I loved this snapshop from Style on Track.  I love the look of the classic hat & tights juxtoposed with a hipster look, which is sort of trashy - a t-shirt, cheap bracelets, messy hair.

Another way I would love to see this (and the way I would wear it) is with skinny jeans or trousers, a fitted wife beater top, and a stacked heel.

With Nothing at All

Two separate Chanel ads show Keira Knightley and Kate Moss wearing bowler hats with nothing but their birthday suits.  When in doubt, rock your hat with pearls!

You can get your own bowler hat from Forever 21 for under ten bucks (shown above).  I also found these great hats by Arth (below) at $55 a pop.

Further reading:  Rags + Zippers, Style on Track, thisislondon.co.uk