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The round-brimmed black bowler hat has come a long way from its beginnings as a symbol of English gentlemen. Snapped up from thrift stores by prop-seeking performers, the bowler has been seen in any number of stage and film productions. Due to a resurgence of menswear as ready-to-wear and vintage-shopping celebs, the sublimely cheeky bowler hat is back on fashion's front lines. Wearing one takes a bit of attitude ... but you've already got that down.
Take it like a man. A bowler hat is the perfect topper for a mix of masculine and feminine pieces. Slouchy menswear trousers, platform heels and a silk pocket shirt make a great foundation for this accessory. If you want a more feminine vibe, pair your bowler hat with a sheer floral maxi-dress and ground it with black opaque tights and lace-up black boots.
Sport a vintage vibe. Clothing from certain eras pairs naturally with a the drop-dead chic of a bowler. Picture a vintage tweed Chanel suit with ropes of pearls and your bowler hat. If you're feeling a bit mod, try a '60s color-block shift or '70s Pucci-print minidress. Add a pair of white patent-leather boots and you'll be stopping traffic.
Sass up your cocktail dress. A bowler hat can give a coy flirtiness to a strappy cocktail dress, especially if it's black and beaded or has swingy fringe. Watch Diane Lane in the film "The Cotton Club" for inspiration. If you're celebrating an anniversary with someone special, you can also use your bowler apres-dinner for an impromptu dance routine.
Play with shapes. Because of the bowler's round shape, it can be fun to play it off hard edges and straight lines for an interesting fashion juxtaposition. For this reason, the bowler looks amazing with an elongated cat eye, a blunt-cut bob or bold, spiked jewelry. Even a black-and-white pattern with hard-edged graphics such as squares or triangles will make the curves of the bowler pop.