No big loss - I hear those are real ugly shoes.
Back in 6th grade I had a pair of lace-up shoes that looked like a dressy sneaker. They were plain white and made from thin, hard leather. I’ve been looking for something like them ever since, but have had no luck. They made my feet look nice and dainty.
I also miss the funky tennis shoes I wore back in elementary school. Nike had some that were either pink or blue satin (I had pink), and then they came out with white shoes with a rainbow swoosh. They really showed off one’s friendship pins to advantage. Of course I wouldn’t wear them now, but they were fun back then.
Converse Chuck-Taylor canvas All-Stars that are MADE IN AMERICA.
Sadly, I only own nine pair at the current time.
A hemp sandal with roman lacing and my Ocean Pacific zori’s
Wow. It seems I’m not alone in my reverence for shoes long past.
I found myself in a shoe store last night, in fact, and found myself in the hiking boots section yet again, searching in vain for the shoes that could replace those old Nikes. Nothing. Sigh.
Though my current pair of sneakers may be getting to that insanely comfortable, just-broken-in stage. If they can stay there for a year, they may give those old ones a run for their money.
It seems my best shoes are always purchased under duress.
In the summer of '92, I was visiting Britain with some friends when one of my shoes died. We were in Edinburgh at the time. Since we were doing a lot of walking, this was something of an emergency. So we went to a discount shoestore in sight of Edinburgh Castle, and I bought some Oxfords. I wanted Doc Martens, but I couldn’t afford them. I bought the nearest facsimile I could find. They were still pricey. I wore them all over England and Ireland for two weeks, then brought 'em home and wore them for another three years - almost every day - until the insides finally wore out. The leather and soles were still in goodshape, but the insides were trashed. One time I had polished them and left them sitting on the kitchen counter when my grandfather arrived and asked whose they were. “Oh, those are Winnowill’s nun shoes,” said my dad. My grandfather was shocked. 
I have REAL Doc Martens now - I don’t like them as much.
The shoes I know I will regret deeply when they meet their demise are another pair bought in an emergency. I evacuated the American Express Tower on 9/11 in pumps with 2 1/2" heels. I couldn’t get back to my hotel room (and did not get my stuff back for another three months), so shoes were a definite priority. The three of us told our boss that we would be purchasing and expensing clothing - my boss said “Fine. Just don’t go to Saks’.” I did go to a shoestore that day and just said “I’m going to be doing a lot of walking; I need something that is comfortable.” He brought out a pair of black Munro Striders, I tried them on, and, without even asking how much they cost (which still amazes me), bought them. They are the most expensive shoes I’ve ever bought (I got my Docs on clearance), and I wear them all the time - including to work a LOT. The insoles (which are removeable) are wearing out, and I’m trying to track down some replacements.
I miss horseshoes the most. Is that not great recreation?
After that, some old Tony Llama roughout inverted pigskin boots. Man, they were slippers for the soul.