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I personally own the Pammy (the red suede shoes in the collage above) and the Lydia (the gold low-heel sandals in the collage above, though in a different color), and they are amazingly comfortable and come in a width that let my toes wiggle and the balls of my feet relax with space

Kennedy went on display in San Francisco Thursday morning

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That said, if this is a concern, you may find yourself feeling more comfortable when you wear one or two vintage items in the context of an outfit that also includes modern pieces

While this may look like a hefty heel, the front platform helps lower the heel drop to a measly inch for a more comfortable stride without being clunky