The chilly weather is officially here, so it's time to ponder this fashionable headwear conundrum: to brim, or not to brim?

The trendlet

This winter, we brim. Once-fashionable newsboy caps and 1920s-inspired cloches have been replaced by the sultry fedora. The wider the brim, the better.

Where's it come from?

Back in the 1930s, actresses Ingrid Bergman and Greta Garbo popularized fedoras - once solely the domain of men - for women. In 1977, Diane Keaton made the brimmed bowler her own in Annie Hall. Until the early 1980s, fedoras were trending in the chic working woman's wardrobe.

As our tastes grew more casual in the following decades, hats became more functional than stylish.

But in 2013, as Baz Luhrmann's The Great Gatsby fueled an interest in '20s fashion, young women inspired by the vintage looks began toying with headgear from that era. Almost three years later, we've crossed into a '30s throwback moment.

I'd be remiss if I didn't mention the Vivienne Westwood wide-brimmed hat that singer Pharrell Williams has managed to make his trademark. We may have giggled when he wore it to the Grammys this year, but it appears that the singer of "Happy" fame was onto something.

Who's wearing it?

In recent months, celebrities from Rihanna to Madonna, and even friend-in-my-dreams Sarah Jessica Parker, have all been photographed in fedoras. During the summer, festivalgoers paired straw hats with cutoff shorts. Not only were they cute, they also protected wearers from too much sun. As fall gives way to winter, well-dressed women from bankers to baristas walk coolly through town with brims shading their eyes.

Would Elizabeth wear it?

I wear hats only when it's cold outside. And then I prefer the classic newsboy. #endofstory

Should you wear it?

One false move and you will look like you are trying too hard, so wear a fedora only if you are confident in your personal style. Got that? Then your fedora will put the finishing touch on pantsuits. And try to match your fedora to a jewel-toned wool coat for a look that's both monochromatic and warm.



Model: Pax Tandon