Petits Chapeaux

Here at Who What Wear, we don't discriminate when it comes to hats. In fact, you might say we have a soft spot for all kinds of chic toppers, from berets to newsboy caps to floppy-brimmed styles. That said, we're particularly excited to channel menswear chic with fedoras and bowlers come fall! Yes, folks, we're talking about the smallish, old-school styles donned by iconic characters like Humphrey Bogart's Rick Blaine in Casablanca or Charlie Chaplin's The Tramp, respectively. These days, however, we're seeing said hats on some of our favourite female trendsetters and paired with thoroughly modern ensembles. From Katie Holmes' borrowed-from-the-boys outfit to Ashlee Simpson's girly styling choices, today's How They Wear story proves there are a variety of stellar ways to don a small chapeaux.

If you're not quite sure about how to style this type of hat, fret not because we have some ideas! One option is to emphasis the hat's boyish nature by pairing it with menswear-inspired pieces, as Katie Holmes and one exceptionally well-dressed civilian recently did. Holmes was snapped out and about in New York earlier this month wearing a slew of simple separates with her chocolate Giorgio Armani fedora, including a Celine sweater, Levi's denim jacket, Madewell pants, and Cole Haan's Air Colton Saddle Oxfords ($198). We think this look works particularly well because of her decision to opt for oxfords, which complement the masculine topper perfectly. We also spotted a stylish show-goer with the same idea as Holmes at the F/W 11 collections during Milan Fashion Week. She went for an all-out laddish vibe with her ensemble, which consisted of a structured tweed jacket, slim jeans, black leather loafers, and a bowler. Again, we appreciate the nod to homme dressing and think it makes for one remarkably au courant outfit!

Of course, pairing the versatile chapeaux with manly accents isn't the only way to wear it; if you want to add a feminine twist, simply consider Fearne Cotton and Ashlee Simpson as your sartorial guides. At the airport in London recently, Cotton effectively made the bowler more girl-friendly by juxtaposing it with a pair of bright pink mary-janes from Topshop, resulting a spot-on boy-meets-girl outfit. Simpson was on the same chic page as Cotton when she attended a birthday party in Los Angeles earlier this month. For the event, she donned a sweet frock with ruffled hemline, which she styled with a noir blazer, high-heeled booties, a cross-body bag, and a sleek fedora. Although both Simpson and Cotton did add a masculine piece to their outfits-the black blazer-their overall ensembles were decidedly ladylike, thanks to their dainty finishing touches.

Now that we've given you the run-down on both the masculine and feminine ways to wear these petite hats, allow us to introduce yet another way to style them: with fantastic outerwear pieces a la Chloe Moretz and Emma Watson! (When we said these toppers were versatile, we weren't kidding!) With a basic black bowler perched ever-so-nonchalantly atop her head, Moretz arrived at LAX earlier this month in a leather biker jacket and a pair of equally tough combat boots. We will definitely want to emulate her stomper-chic outfit when the weather gets chilly come fall and winter! We're just as enthralled with Watson's choice of cold-weather gear; she protected herself from London's fickle weather a couple months ago with a Burberry Prorsum trench coat, Zadig & Voltaire Ailes Strass Ballet Shoes ($286), the Mulberry Carter Double Handle Bag ($1550), and a fedora. We particularly love how she expertly mixed the trendy chapeaux with classic, always-in-style pieces, resulting in one perfectly balanced ensemble.

Convinced you need to own one of these of-the-moment hats pronto? You're in luck because we've rounded up the best of the best for your shopping pleasure! If you're not willing to make a huge splurge, consider snagging Tarnish's Wool Bowler Hat ($38), Brixton's Pack Straw Bowler ($38), Goorin Bros' Samson Hat ($110), Comme des Garcons' Blue Wool Hat ($133), or Calvin Klein's Double Wrap Herringbone Fedora ($45), all of which will make a superb addition to any look. Searching for some higher-end options? We've got you covered there as well! We think Borsalino's Wool Hat ($485), which comes in four amazing colours, and CA4LA's Felt Bowler ($215), and Eric Javits' Velour Fedora ($375) are top-notch choices that can be worn all season long. Whichever one you choose, we promise you'll never want to take off your stylish new hat!-Erin Fitzpatrick

Photos of Chloe Moretz and Fearne Cotton, courtesy of Bauer Griffin; Photo of Ashlee Simpson, courtesy of x17; Photos of Emma Watson and Katie Holmes, courtesy of Splash; Street Style, courtesy of Imax Tree.