Have you considered adding some nice insoles? I've got Superfeet Blues in my Converse All-Stars and they add the perfect amount of shock absorption and arch support. It's a great way to keep the classic look while upgrading to a modern feel.

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Definitely Schmoove. You can buy them from http://www.asos.com

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boat-loads of comfy stylish shoes.

http://www.sketchers.com

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I think it really depends on your arches and what your doing in the shoes. Here are some of my recommendations.

Puma Speed Cats

Also Pro Keds

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Fluevogs0=gender%3Amen&w1=attribute%3AShoe&pp=1&view=detail&p=15&colourID=2543

also,

Zuriick

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I wear Cons and Vans all the time but the durability and comfort is definitely an issue. Lately I've really been into Sperry Topsiders

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I bought a pair of New Balance 420's after seeing them featured here. They are pretty slim, but not as slim as Van's Slip-On line of laceless shoes. They are, however, incredibly stylish and are with the perfect amount of 'retro chic.'

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I switched to wearing Toms shoes

The majority of their shoes have a canvas upper with a leather insole and rubber outsole. I would say they feel very similar to converse but more comfortable, and they have the slim shoe look your going for. They usually run between $40 and $65

Also the company donates a pair of shoes to children in need when you buy a pair.

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