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Accessory Report

Accessory Report: 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 favorite men's Prps Barracuda Jeans ($380, 212.966.0464) and menswear-inspired button downs, like Steven Alan’s Fall Reverse Seam Shirt in gray/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 adapter, 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 colors, 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.
COMMENTS (25)

i really like this look. it can be really retro so i'd wear it with something feminine and modern. the heeled ones are too chunky for my taste though.

Posted by: Alex |  2009-01-29 22:13:44

My Lord they all look so hideous! And what was Katie Holmes thinking? She looks like a boy! Horriblee!!!

Posted by: Ilianexy  |  2008-10-13 16:49:44

not really into this...but the Marc by MJ ones are beareable, i guess.

Posted by: rr |  2008-09-30 13:08:15

penny loafers are ugly as fuck. they look like teachers without style.

Posted by: jamie |  2008-09-29 21:54:39

Just like Sara, this post reminded me of boat shoes which I much prefer to penny loafers...they look more stylish and seem to be more comfortable too. http://mimisview.blogspot.com/

Posted by: Mimi |  2008-09-29 19:38:22

i looooove this!!!! i just bought a pair from paris. It was from Tod's Fall/winter09 its patent black theres also another one in white. looks very cool with ripped skinny jeans and a blazer or a tuxedo jacket. u can find it on tods.com

Posted by: TNN |  2008-09-29 18:57:23

It was a privilege to wear loafers when you got to the 7th grade in my school, but when you graduate as a Senior you really don't want to see those ever again!!!!

Posted by: Edmee |  2008-09-29 18:29:39

i do not like this look whatsoever. the marc by marc jacobs ones are cute, i guess but the blue patent is a huge turnoff. i think moccasin loafers are way cuter

Posted by: r |  2008-09-29 16:41:52

love this trend! i bought a pair in late august from urban outfitters, $32, olive green, they're adorable and extremely comfortable...ive been wearing them with more preppy pieces, but i might try something more edgy. i feel ahead of the game since i bought them about a month ago...but i love you wwwd!

Posted by: dana |  2008-09-29 16:20:22

I'm not a massive fan, but I quite like the way Kirsten is wearing her's. :)

Posted by: Amy |  2008-09-29 14:15:28

i dont think i could pull off this look. but i like the mark jacobs ones! but $245 for penny loafers is too steep.

Posted by: lianna |  2008-09-29 13:41:40

alexa's been wearing these for a couple of years.

Posted by: Jane |  2008-09-29 13:40:16

Loafers are one trend that I don't mind revisiting every few years. They'll be a nice alternative for winter, especially with the legwear available this year.

Posted by: K |  2008-09-29 10:05:16

Yessss finally some flat shoes that are stylish, versatile, fall appropriate, and great. I've always loved loafers, I'm glad that they're in! I'm going to go buy some soon...

Posted by: Taryn |  2008-09-29 10:01:36

Cute... reminds me of the 90s. They look super comfy!

Posted by: fashi0nlover |  2008-09-29 08:46:04

Surprisingly, I like Kelly's outfit best, especially the wool cap and plaid jacket. I'm usually a fan Kirsten's outfits but the dress (if you can call it that) is just way too plain. It looks like a prison nightgown.

Posted by: Caitlin |  2008-09-29 08:37:31

i don't approve of loafers with dresses. at least put some knee socks on or something.

Posted by: hmmm |  2008-09-29 08:25:21

I think Kirsten looks cute but the shoes do nothing for poor skeletal Alexa's chicken legs. Her feet look like water skis!

Posted by: MEP |  2008-09-29 08:08:17

you can get really cheap and cute penny loafers at urban outfitters, too.

Posted by: antoine |  2008-09-29 07:17:06

I think they´re Cute! I can borrow my mom´s :) Check my fashion site out! http://icelandicfashist.blogspot.com/

Posted by: helgakay |  2008-09-29 06:08:47

isnt loafers quite last season?!

Posted by: Desiree |  2008-09-29 05:45:53

katie holmes looks redunkulous !

Posted by: valerie |  2008-09-29 02:42:53

disgusting! that is one trend im never trying.wwwd quit trying to make us follow the examples of holmes and osbourn!

Posted by: izzy |  2008-09-29 01:12:46

i love penny loafers and boatshoes (i think of them as similar and one-in-the-same when dressing), they can be worn almost with a grunge aesthetic. http://sarazucker.tumblr.com

Posted by: sara |  2008-09-29 00:30:01

I like it! These ladies are wearing styles that are classy without being too old-lady. http://ebayfashionaddict.wordpress.com

Posted by: Elana |  2008-09-29 00:09:11

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