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Vans Prison Issue #23

Vans Prison Issue #23

Vans made these laceless canvas sneakers back in the day for those unlucky souls in California prisons. Apparently, shoe laces are more dangerous than the velcro straps found on the Vans Prison Issue #23 ($50). And if the blaze orange doesn't match your jumpsuit, the kicks also come in black, green, purple and yellow.

  • Converse Jack Purcell

    When it comes to style, simple is always better than complex and gaudy. These lightweight canvas sneakers ($50), designed back in the day by world champion badminton player Jack Purcell, are most definitely simple and easy on the eye. With their signature blue "smile" on the toe and light blue rubber sole, they're the perfect match for a pair of khakis this spring. The latest version has been updated with a ½ inch thick comfort insole, lightly padded tongue and upper sockliner. Think of them this way: compared to the classic Chuck Taylor All-Stars, the Purcells are less street punk and more preppy dad.

  • Converse Camo All Star

    Converse’s Chuck Taylors have been associated with “cool” since their debut in 1917, when they were known simply as the All Star — the Chuck Taylor on the ankle patch wasn’t added until 1923. The latest version to catch our eyes is the Camo All Star ($45). The classic cotton canvas uppers and rubber soles keep your feet comfy, while the camo print keeps you looking great — whether you wear them with jeans or cargos.