Until they leak in the rain. If my feet get wet walking across wet pavement, either through the sole, because the sole and upper are separating or a hole in the side, I retire them.
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Oh man, that's when they just start getting comfortable..
As long as I can is how long I wear mine out. At least until they start to become a real problem, like starting to really fall apart. If possible, that is. I just enjoy wearing my shoes to the max to ensure I get the most out of them.

Had for two years, use mink oil, leather has however degraded.
Also worth mentioning, these are soon to be replaced. Not worth resoling as got for £60
Shit homie, don't throw those away!
I'd just as soon finish wearing them out myself if they're around US size 10½ to 11½ or so..
Dibs if they're US 9-10
Those look good to me. I wear the shit out of my shoes.
Fresh clean shoes are lame. I like looking down at my feet and seeing all the life and work I've worn into my shoes. I've a pair of boots for snow, a pair of sneakers, and one pair of sandlas. That's it- if you invited me to something fancy, well, I won't be invited anywhere fancy I assure you. I'm 38 and never even been to a single wedding. Ha.
I'd have to upgrade to flip flops for a wedding LMFAO!
👍

Here's the one on my right foot right now.
Holy shit dude, you'd be doing those shoes a favor by walking through a reasonably clean ditch or deep puddle LOL!
If I did that, the hole in the side would let my sock get all wet, lmao
Lots of paint, joint compound, and caulk made these shoes look this good XD

These are the EVA birkenstock sandals
They ended up ripping through and not really usable anymore because the whole front flops.
Beautiful! 👍
One of two things, which ever happens first. The tread wears and a part goes all the way to the sole or the tread wears and I fall down on the hill by work when it is raining or snowing.
jfc, man. riding BMX in these? no wonder they're shredded...
if you need durable all-purpose shoes that are still comfortable enough to wear all day, i recommend light patrol boots.
Meh, I don't ride flatland nearly as often these days as I used to 10+ years ago, but yeah I still get out and practice once in a while for the exercise.
But yeah, not only flatland, but brakeless flatland, that'll definitely tear some shoes up, especially with tricks such as footjam tailwhips...
My fiance, like her dad, uses old shoes for when we go to her family's farm and they have a bonfire. For kicking burning stuff back into the fire. Unlike her dad, she's 5-ft tall. I'm 5'10" and I use a fucking shovel like a sane person for that job. Keeps me from melting my shoes and lowers my risk of dying horribly.
I wear heavily cushioned shoes for comfort, and the common tradeoff is they don’t have an outsole to reduce weight. The midsoles have direct contact to the ground and since they are super soft, they wear out fast if you regularly wear them. Once I start losing traction or I can feel the ground through the soles, it’s time to replace them.
I start with a pair of good insoles, then as those wear down I buy another, and another, and so on until the shoe tread wears out or holes appear in them. If you buy some of those magic eraser pads, you can usually keep the outside of the shoes looking relatively new for a lot longer as well. I have some shoes right now that are going on ~1.5 years and I'll probably get another 1.5 out of them.
Pro-tip: don't buy the cheapest shoes you can if you can afford it. I used to buy $20 skate shoes and they would wear out in less than a year.
Meh, I prefer cheaper shoes to an extent, as I know I'll eventually destroy them.
My main requirements are:
-
- Good comfortable fit
-
- Easy to put on and take off
-
- Well ventilated to evaporate sweat
-
- Bottom sole is preferably the yellow rubber anti-skid stuff good for potentially oil-slick surfaces
I wear them until I know when I’ve stepped in liquid.
I can replace insoles, I can mend the uppers, but once the soles start letting water in, then it's time for retirement.
Guess that's a skill I should learn.
Protip: E6000 craft adhesive works magic.
E6000?
You son of a bitch, you reminded me of my old project, my custom modded game controller!
I did lots of mods back in 2003, but the plastic is getting brittle these days ☹️
E6000 was used to secure my modded parts.
I really should at least try to fix the remaining parts and give it another game drive, even if it requires some duct tape..
If I can't see the floor through them, I'll keep wearing them.
Oh, so early?
My winter boots is during its 7th winter now. The last one.
Leather is still good, but upper part has not decent look. But the worst part is it not warm enough anymore for russian winter.
Laces was changed, heel counter was patched, sole was glued.


Ooo ooo I love good work boots!
I bought these in 2015 for work. I left that job in 2020, and I wore these like three times since. Pulled them out this winter for my son to wear as the fit him right now, (he's growing and blowing through shoes).
How bloody happy I am that after ten years, they are still holding up! You can see some of the leather is wearing, but they're soaked on the outside in these photos, bone dry in the inside.
Fuck inflation though, I paid $120 for these back then, the same boots, I looked them up, today, are $230. Wild. No way I can buy these kind ever again, I'm so happy they have lived so long my son is now getting life out of them! Will definitely be getting these repaired when the time comes!


Where it gets really crazy is where you have a few pairs that you rotate through for "daily wear". A whole decade can slip by before you go "how long have I had these?"
I don't care a whole lot about fashion so "until they stop working correctly" is about the best answer I can give.
Even crazier when you started working from home at least part time since pandemic, so the shoes you’d normally wear to work get little use.
I got divorced about five years ago and still have a closet full of shoes I apparently needed but they’re all unworn so I might have a lifetime supply
Upvote for extra shoes 👍
I wear leather boots, ankle high. The shoe store fixes em when the bottom wears out. Had em 11 years and they're still fairly pristine. Just gotta oil em every winter. Probably should do that more often.
It was $600 and $50 or so every couple years. Figure I've gotten it amortized down.
I wear them until they reach zero on the comfort scale:

- 10 - The most comfortable thing in the universe. You don't even know you're wearing them
- 0 - It actively hurts your feet
Is this scale measured in years, months, or hours?
Technically, if it's measured in one, it's also measured in the others.
Usually until I have a hole in the bottom or they start to stink that even washing them doesn't help.
Wait, you wash your shoes?
I only do that when I stepped into a doggy landmine..
Edit: How do wash shoes without damaging them?
Yeah I do once a while which also gives them a week of rest before I go on with them. You just don't dry them in the dryer, you air dry them.
People think I am nuts, but I only have 1 pair of sneakers and I try to make them last at least 2 years, if not 3, before getting a new pair. I know its time if they are failing apart or I start to realize my feet hurt and its most likely due to the worn out shoes that have no more comfort or cushion.
Until they break, then they're yard shoes
No shoe thrown away
Yard shoes?
I actually like that term, makes sense 👍
I call these my junker shoes, for general everyday use, as I hardly give a shit anymore, as I have other nicer shoes for more formal occasions.
Yeah my yard shoes are there to cut grass and turn green lol
When they start getting wet when it rains. Currently my favorite pair wears out in less than a year.