Penny Loafers

Preppy style never really dies; it just excuses itself to refresh its gin and tonic and accidentally wanders away for a few years. Though we tried to ignore the signs that WASP-y wear was asserting itself again (pastel polos with popped collars, we're talking to you), we couldn't help but notice that bastion of boarding school cool-the penny loafer-is poised for a major comeback. It seems like everyone's adding a spoonful of Upper East Side chic to their shoe shelves, as an astonishing range of celebrities (including Kirsten Dunst, Kelly Osbourne, and Katie Holmes) are wearing preppy pairs of leather loafers.

Whether you blame the footwear fad on the knee-sock-and-headband-wearing style of Gossip Girl's Blair Waldorf or a subconscious desire to bring back the early eighties bull market era, there is no denying that loafers are appearing on a diverse bunch of feet. Last month, Kelly Osbourne paid a visit to Radio One in a pair of Chanel loafers (hers are from Spring 07, but check out this season's patent version ($695, 800.550.0005) online now) and a House of Holland plaid jacket. Though this might sound like a recipe for an ultra-traditional look, Osbourne kept her outfit edgy by wearing these two preppy pieces with a slouchy wool cap and skinny black pants (nary a ribbon belt in sight). Classic dresser Katie Holmes is another penny loafer proponent. She's been spotted all over New York wearing this shoe style with her favourite men's Prps Barracuda Jeans ($380, 212.966.0464) and menswear-inspired button downs, like Steven Alan's Fall Reverse Seam Shirt in grey/white check ($158). We like the slight cuff on her wide-leg jeans, it's a subtle nod to a Father Knows Best, bobby soxer style, but the faded wash keeps things looking modern.

If you didn't believe that pennies, as we've nicknamed them, have wide appeal, please take a look at Exhibit C, Kirsten Dunst. The actress introduced her directorial debut, Welcome, at the Palm Springs International Shortfest last month wearing a dressy, tassled pair of Les Praries de Paris Les Roccos Loafers ($367.50, on sale) with a vintage dress and Isabel Marant bag. Flat footwear-lover Alexa Chung sported some similarly shaped shoes during London's Fashion Week (an early adaptor, she started wearing this accessory du jour a few months ago). Seen above at Christopher Kane's S/S 09 show, Chung wore her trusty Russell & Bromley Black Patent Fringe Tassel Loafers ($230) with a graphic Louis Goldin jacquard knit dress and one of her beloved Mulberry bags, specifically next season's Shimmy ($1195, 888.685.6856), in taupe.

Right now, there's a lovely selection of penny loafers to indulge in guiltlessly. Merona's Maddison Loafers ($24.99) are a fantastic frill-free version of the trend and are available in warm brown leather. If you're slightly more daring, Topshop is stocking Kasbien's Penny Loafers ($125) in lots of cool colours, like raspberry (shown above), cobalt, a leisure suit-appropriate white, and basic black to boot. On a slightly fancier note, we also like the electric blue look of Marc by Marc Jacobs' Patent Leather Loafers ($245). The slim shape is a bit more like a driving shoe; it's perfect for the girly girl types. Finally, for those readers who go nuts for the traditional and the tasseled, we'd like to suggest the Bass Loafer ($98). We have a feeling that the timeless shape and smart price point will fit your footwear bill perfectly!

Photo of Alexa Chung, Kirsten Dunst, and Katie Holmes, Getty Images. Photo of Kelly Osbourne, Splash News.

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