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  • Wingman Grey
  • Wingman Grey
  • Wingman Grey
  • Wingman Grey
  • Wingman Grey
  • Image 6

Wingman Grey

Modern meets classic in this traditional canvas sneaker with lace-to-toe design. With an old school vulcanized rubber outsole and Memory Foam orthotic insole, the Wingman is designed for maximum slip resistance, comfort and durability.

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Estimated Ship Date March 26


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Pre-Orders Only. Expected Ship Date March 26.

Product Reviews

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  1. Great shoes 5 Star Review

    Posted by on Jan 5th 2017

    If it helps people pick the right size, I went with my normal 9.5, and they fit great for my wide feet. They're not too big at all. But everyone's probably right that they do run large, and are great casual wider width shoes.

  2. The gift that keeps on giving 5 Star Review

    Posted by on Dec 8th 2016

    I bought these for my brother in law so I cannot attest to the comfort and fit just yet (although I love my Simple shoes)....however, they look like a very good quality shoe and a pretty gd stylish!

  3. Love 'em! 5 Star Review

    Posted by on Oct 25th 2016

    I have had several pairs of Simple shoes, going back to when I was in law school 20 years ago. I ordered the Wingman shoes, once I learned that I could again get Simples, and I love them!

  4. Great Shoe! Runs large, ladies 5 Star Review

    Posted by on Aug 8th 2016

    If you love the Chuck look but would prefer a higher quality shoe- this is what you're looking for. For my fellow tomboys out there- be warned that these shoes run large when you are converting womens sizes to mens. I wear a 9.5 in women's and purchased a 7.5 in men's. There's a bit more room in the toe than I'm used to but it's not too bad. That aside- they are super comfortable and the exact style I was hoping for. Love these!

  5. Wingman 3 Star Review

    Posted by on Jul 26th 2016

    OK shoe. Length seems a longer than normal..

  6. Love em 4 Star Review

    Posted by on Jun 1st 2016

    Ive always liked the look of classic Chuck Taylors, They simply don't fit very well and don't offer much in the way of all day support. These are so much better for my wider feet and taller arch. The memory foam insert feels great. Cool, comfortable, supportive. These have become my go to shoes for summer.

  7. Nice shoes 4 Star Review

    Posted by on Apr 12th 2016

    Really like the shoes very comfortable, they just run a little larger. Might go a half size smaller next time

  8. Look great, but beware of sizing 4 Star Review

    Posted by on Mar 17th 2016

    I've been wearing simple shoes since the 90s, and I'm thrilled they are back. I ordered these shoes (along with the OS Sneaker) in the same size that I've always worn, 10.5. When I got them, these shoes were a full size too big, and the OS sneaker was about a half size too big, so I had to exchange them. I got a 9.5 in the Wingman, and it is still boarderline too big. I could probably do a 9, but i didn't want to return them again. The OS sneaker, i returned and got a 10, which seems to be working out.

    They are comfortable, great style, and I'm certainly happy with my purchase. Just be aware that simple shoes now run inconsistently big, so be prepared to return them.

  9. Better Than Expected 5 Star Review

    Posted by on Mar 3rd 2016

    I was in love with Simple shoes in middle school and was always impressed with their comfort and durability. Happy to say that hasn't changed with this new release. Don't let the deceivingly (ahem) simple design fool you, there's padding in the tongue and collar and the Memory Foam insole allows for long walks without discomfort. Really the best of both worlds, timeless looks, contemporary construction, comfort, and durability. Simple!

  10. Great Sneakers! 5 Star Review

    Posted by on Dec 17th 2015

    Super comfortable and look great! They didn't take long to wear-in at all. They don't have women's sizes yet, so I bought a pair of men's size 7 for my women's 8.5 size feet. The shoes are very roomy in the toe. I've been waiting so long for another pair of Simple Shoes sneaks and I was not disappointed!