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Converse By John Varvatos Chuck Taylor Vintage Slip-on
"I travel about four times a month. These shoes are great for walking around, and they're easy to get off and on for airport security. Besides being practical, they are visually inspiring. I admire how John Varvatos has re-created a sneaker that is part of our fashion iconography," says Jason Pomeranc, co-founder of the Thompson Hotel Group.
COST: $95 at John Varvatos.