26 reviews

OS Sneaker Cherry

Unisex Sizing: Size Guide
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free shipping orders > $100

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Free Returns and Exchanges

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satisfaction guarantee

classic skateboarding shoe from the '90s is now your casual everyday sneaker

Known for its skateboarding prowess in the 90's, the OS Sneaker has grown into a legendary casual shoe for street wear. Simple’s flagship style, the OS Sneaker has stayed true to the ideals upon which Simple was founded. Clean and minimalistic in its design, the OS also provides long lasting comfort with a Purefit insole.  Outsoles are made of recycled rubber and contain no harmful chemicals.

  • Premium Suede Leather Uppers
  • Fabric collar and linings for breathable comfort
  • Purefit insoles for comfort
  • Long-lasting stitched down recycled rubber outsoles

"...the Original and Best" - GQ Magazine.

"perfect for those days when you want to keep it low key" - Complex


Care Tip:  Be sure to spray your Cherry OS's with suede protector to keep that Cherry color lasting as long as the shoes! 

Orders & Shipping - North America

FREE shipping on all US Orders over $100.  Under $100 is flat rate of $4.95.

FREE shipping on Canadian orders over $120. Under $120 is flat rate of $20.

Orders are processed and shipped within one business day.  We ship using USPS Priority Mail.  Once your order has shipped, you will receive an email containing your shipment tracking number which you can use to track the delivery status.   

Orders & Shipping - International

We ship to most countries for a flat rate of $45.  

If you have any questions about international shipping please contact us and we will be happy to help you.

International orders are subject to your country's import and customs regulations.  This may result in added time and costs.  Any duties or taxes related to international orders are the responsibility of the customer.  In our experience, Customs Duty Tax is levied on about 10% to 15% of our orders and can range from $30 - $50 USD in addition to the shipping charges below.  So you need to really want your Simple Shoes:)

Start your Return or Exchange Here.

Returns & Exchanges - United States

FREE Returns and Exchanges as long as:
  • You made your purchase within the last 15 days. 
  • Your products are unworn, resellable and in original packaging. 
  • Note - Sale / Last Call items are not eligible for Refund, but are eligible for Exchange or Store Credit.
Refunds are processed within 24 hours after receipt by warehouse (excludes original shipping fees). 

Returns & Exchanges - International

Due to the added complexity of shipping internationally, we are not able to provide a free return shipping label.  However, we will gladly exchange or refund once we receive your returned goods that you've shipped using the carrier of your choice. 
Customer Reviews
5.0 Based on 26 Reviews
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Peter H.
United States United States

awesome sneaks!

These shoes are amazing. I had several pair in the early 90's and also loved them, but then I lost track of them and thought maybe they weren't made anymore. I am going to buy another pair now for backup in another color. In the fit description it says the shoes tend to be medium or narrow fit. I have wide feet, and these fit great- just loosen the laces and you're golden!

Genna d.
United States United States

My New Red Shoes!

What can I say? My first pair of Simple shoes since my original pairs wore out that I bought in the early 90's when I was first introduced to this brand at a mountain bike festival at Mammoth Mountain, CA! Love my new red sneakers!

Donald N.
United States United States

So comfy and stylish

Love them. I’m a 9.5 in Aasics and Nike, and there is a tad bit of space from my big toe to the end of the shoe in these that has me wondering if a 9 would be better…but I’m not returning them to find out! They are wicked.

Kathy H.
United States United States

OS's are Awesome! Now I want the new clogs.

These OS’s are so comfortable they fit like gloves and I can wear them comfortably for hours. I get compliments from strangers all the time! I hear they are great for skateboarding but unfortunately I am not good at that. I love the cute, thick shoestrings and the Red color is awesome and goes with everything. Next I want the new clogs, they look so cute and easy to get into and out of.

Canada Canada

We love all our Simple Shoes - especially these in Red!

We have been fans of simple shoes for about 10 years, but now we live in Canada. Thankfully Simple Shoes ships across the border so I ordered red shoes for both myself and my daughter. At one point I was concerned about the delivery so I sent a message to customer service; I got an immediate response saying not to worry. Staff were tracking my shipment and would continue to do so until we got our shoes. It took a bit longer because of Canadian customers but they arrived last week. Of course, they are great. I got another pair of OS', this time in red (love the color). My daughter was also looking very fashionable with her red Simple sneakers. Thanks again Simple Shoes! We will always look to you to get stylish comfy shoes.

Maria verified customer review of OS Sneaker Cherry