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Men's Shakespeare Circle Loafer





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94% of customers say this fits as expected

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"Oh, darn! It's that time again! It's been seven or eight years since I ordered a new pair of Shakespeare Circle Penny Loafers. I've lost count of how many pair of these I've worn over the years. I keep expecting Rockport to discontinue them, as the penny loafer isn't exactly high style anymore. But for those of us who don't really pay attention to the latest fads, who are looking for a "classic" good looking shoe that is both comfortable and long-lasting, look no further. Yes, they are pricey, and there was a time when I tried to replace them with rip-off discount-store look-alikes, but my hips, legs, and feet soon made quite the complaint that I had erred. If you realize that paying $30-$40 for those discount brands that only last 6 months and add in the cost of visits to your local podiatrist, orthopedist, or chiropractor, you're better paying up front in the long run. (So you just keep an eye on things until Rockport has a sale.)"

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The craftsmanship of the Shakespeare Circle is evidenced in its hand sewn construction, lending these penny loafers their classic, quality styling. Inside, truTECH® sport technology in the footbed helps to protect your heels at ground impact. Adding to the slipper-like feel are flex grooves for forefoot flexibility and lightweight, resilient cushioning that keeps you moving comfortably all day long.


  • truTECH® shock-absorbent cushioning protects the heel at impact
  • Padded collar and tongue for comfort
  • Full-grain leather is durable and easy to clean
  • Flex grooves in outsole offer forefoot flexibility
  • Breathable polyurethane cushioning for moisture absorbency and odor resistance
  • EVA helps to provide lightweight shock absorption to reduce foot and leg fatigue


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