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First he justified his standing as a solo superstar after leaving *NSYNC, before bringing Sexy Back to the charts a few years later.

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When it comes to men’s footwear, some styles are too classic to ever let go. You can’t get more authentic than a fine pair of Dan Post cowboy boots.

For a real blast from the past, try out some Chuck Taylor® All Star® sneakers or America’s favorite boat shoe by Sperry Top-Sider.

We learned a lot about Gary during this shoot, and what it took for him to be able to make his passion into his career.

Learn more on Ip H is a brand that understands the space it lives in, and this season it's introducing a whole new line of product, Sensor Flex - launched by t Witch along with other dancers like "So You Think You Can Dance" Virgil Gadson - which brings a sneaker-like sole to Timberland boots." Check out this awesome feature by Pete Forester in Esquire about the style, flexibility and danceability of the new Sensor Flex styles.

So what's next for America's most famous ex-boyband pin-up?