What's the longest you wore the same pair of boots before tossing?

I'm still wearing boots from my first tour in Iraq back in 2006....yikes

I had my Danners for at least 5 years....but only wore them when it was cold, which was a few months a year.

I'm still wearing the boots I was issued in 1984. They're not the most comfortable, hard soled, but have a good shine on them and can still do the job. I went through two pairs of Bates that had the soles wear out quickly on the non-skid.

I still have the first pair I was issued 17 years ago.

They haven't been authorized for wear for the last 7, but I still have them.

Still wearing my pair from basic, they are not stained, and maintained, I also have my second pair from basic which have yet to be broken in. It seems that since moving to the hide boots maintenance is simply not being taught within IET, which among other things is creating the current age of army that lacks standards and discipline. 

I've a pair of boots from my last deployment in 2011 that I still wear

I'm still wearing, and have worn on a near daily basis, the boots I was issued at Parris Island in 2010. Nowhere near as long as some of the others here, but they're comfy and provide more support than tennis shoes do, with the added advantage of "I don't have to spend money on new footwear."

I wore the same pair of boots I was issued in boot camp in 2008 until a couple of months before I deployed in 2013. Replaced the insoles once a year, ran multiple CFT's, boots and utes runs, and daily wear the entire time. They were Bates boots. I did have a separate pair for working parties though. Wore a set of steel toes that I wore once a week (the frequency of being on a working party) from sometime in 2010 until I deployed, and I went back to wearing them weekly after I got back. 

I have boots that I started when I got back from Afghanistan in Nov 2010 so almost 4 years. They have been relegated to boots and utes PT or range duty in the past year so they are not worn daily. They might still be worn daily if work hadn't bought me a new pair of steel toes that I wear on a daily now.

I bought a pair of H & H jump boots in 1992 while in Germany. I wore out the sole and then had them resoled with this wicked looking Vibram sole. They were my pride and joy, shined like black obsidian glass with the kiwi polish. Somewhere around 2003 the leather on the outside of my left foot finally showed a crack finally. I thought I may have saved them in a box somewhere as a keepsake, I'll have to look now.