Cheryl Shops

When I was a child, I always got a new pair of shoes for back to school. These were usually penny loafers—I grew up in a very preppy area—and year after year, I would barely wear them. Eventually my mom wised up and started buying me shoes I'd actually wear (like Keds), but over the years, I've found myself pondering loafers and why they never worked out for me. I think I found my answer: the heels weren't high enough! Thankfully, this season the classic loafer has been updated with a sexier shape and a sky-high heel, complete with platform. It looks like I've finally found the penny loafers I'll want to wear.


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Opening Ceremony's Laetitia penny loafers take the standard penny loafer shape and elements like pinked edges and two-tone coloration, subtly upgrading the look with a stacked heel and a sturdy lug sole. It's a classic, modernized just enough to be irresistible.

Nicholas Kirkwood is currently the object of my shoe lust, and when you look at the dangerously sexy beauty of these tasseled platform loafers, it seems pretty obvious to me. They look like something a librarian who's secretly a dominatrix would wear (a rich librarian-dominatrix, that is), and isn't that reason enough?

Yves Saint Laurent's Tribute pumps are a classic in their own right; here, they've been married with a tasseled loafer for this quirky yet smart take on the trend. I love the contrast between the spindly heel and the fusty fringe; they're like a grandpa with a hot young wife.

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There are so many awesome styles at this price point, it was hard to choose three favorites, but every time I look at Frye's Naiya Kiiltie loafers, I can't help but smile. They're kind of nerdy-cool, and I especially love that they come in navy (as well as three other colors)—a good pair of navy shoes is hard to find.

It's almost hard to believe these Quinn platform loafers are from Banana Republic, but then again, they fit in with the chain's classic, work-friendly vibe. With the hidden platform, they're kind of a platform entree for people who think they're not platform people.

As I've noted many times before, I'm a huge fan of Pour La Victoire shoes, so their Larkin is sure to be a winner. Their shoes are always comfortable and well constructed, and while I'd probably go for the black or brown leather, I love that these come in red patent too.

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Speaking of styles that come in an array of colors, Nine West's Abalene is available even in faux exotics, although I prefer the faux croc (pictured here) to the faux snakeskin (kind of cheap looking). With a 4.25" heel and a 1" platform, these are also one of the most sturdy styles pictured here.

For those of you reading this story and thinking platform loafers aren't edgy enough for you (and can't afford the Nicholas Kirkwoods above), meet Buffy from Charles David. It's obviously still a loafer, but studs along the sole add a downtown finish.

With traditional pinked edges, a sturdy heel, and a lug sole, Mia's Nolen loafers are a pretty solid choice for their price ($59), so long as you don't mind the fact that they're synthetic.