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Vans Vault Penny Loafer LX Vans introduce a new model with their hybrid Penny Loafer LX. Taking the best of both worlds, Vans' signature vulcanized outsole is matched up with a traditional slip-on penny loafer upper. The youthfulness of Vans remains thanks to some unorthodox color...

Known for such iconic styles as the double-buckled William "Monk" shoe (named for founder John Lobb's son) and the slip-on Lopez loafer, the brand follows a rigorous 190-step process for the creation of each pair, which spans several weeks from the initial cutting of the Italian calf leather...

Dior Cherry Red Patent Leather CD Loafers may lack the heels but they definitely have elegant styling. These square toe loafers are made of glossy patent leather upper in red. They have these goldtone 'CD' designs plus boatstitched openings with goldtone grommets. These loafers also have...

She kept it casual with a bit of Parisian flair in a leather motorcycle jacket, black skinnies and black leather penny loafers. To finish off her look, she rocked her beloved Linda Farrow x The Row Shades and Topshop Extra Large Hoop Earrings with a $358 Joseph Stripe Jumper: Her sweater is...

leather outsole. A Goodyear leather welt construction enhances the shoe's overall resilience and durability. The upper features a toe medallion brogue detail inspired by the Trafton, Cole Haan'siconic wingtip named after the brand's co-founder, Trafton Cole. The Monroe Penny Loafer is...

Domingo, Dominican Republic while Fieg was churning out the Sebago Spring 2012 Collection led to this, the Sebago Triple Black Penny Loafer. In complimenting London's unique style, Fieg thought of another unique characteristic to Sebago apart from the label's well known boat shoe, its Classic...

Penny Loafers are great for this time of year because they can look good with almost any outfit. These classic shoes that once seemed cliche to me, are now one of my favorite ways to dress up any outfit. Yes, when most think of this look it probably comes with the image of mid thigh length...

What to wear it with: The Tory Burch Penny Loafer -- currently available in Black, Bison Brown and a delicious Tory Red -- is crafted from Saffiano leather with a 1" wooden heel and a subtle goldtone Tory Burch logo nestled in where the penny would normally reside. These shoes are perfect...

We're not going to wax lyrical about this shoe, the close-up shot above should explain why we chose this loafer from fine footwear makers John Lobb. Black Couchevel calfskin with that fine grain means that very little else had to happen on this shoe, no tricks needed. One of the slickest pair...

With the preppy, collegiate look being one of Fall 2011's top trends, penny loafers will surely be the shoe of choice. But if the clunky classic doesn't do much for your feminine taste, then check out Pour La Victoire's 'Larkin' Penny Loafer Pumps. Pristinely perched on a dangerously...