How far gone do they get before you retire them?
I think I’ve gotten past the age where I can wear jeans with the knees out (a la the Ramones).
Do you wear them with patches all over them?
Embroider them?
Bleach them?
Cover them in chrome or rhinestone studs?
Is all of this passe?
I think I know the answer, but you tell me.
I wear my jeans with boot-cut legs, six inches too long, occasionally cuffed but more often left bunched around my ankles with the hems getting under my heels. I wear them until there are huge gaping threadbare holes in places that there really oughtn’t BE holes.
Is it still cool to have holes in your jeans? In the 80’s having the knees and ass out of your Levi’s (a la George Michael) was de rigeur in my high school. (Did I just write de rigeur and high school in the same sentence? I need sleep.)
Wear them any way you like. I won’t laugh. 
For me, comfortable & soft.
Broken-in and soft. When they get worn to the point of holes beginning to form, out they go.
It’s not cool to have holes in your jeans anymore. I’m too cheap to replace them until they’re completely worn out, though. 
See, I thought the hole thing was out, but I didn’t know. I wish I had the guts to keep a totally thrashed pair of jeans for occasional use. So nobody does anything unusual/ornamental to their jeans? How disappointing.
Broken into and loose , tight around the thighs maybe fashionable but it hurts after a while + made more than 15 years ago since I’ve 8 pairs of jeans from years and years ago that are in pretty good condition whearas I bought some 501s last year and they are falling apart and i don’t even wear them that often.
~~I don’t like my blue jeans
I like my blue jeans black, snug on the hips and to the knees, and then boot cut at the bottom and way too long. Eventually the part that is constantly under my heel wears thin and somehow disappears, and the front part blends in nicely with the black leather, pointy-toes of my boots. The whole thing gives my feet that “Yellow Submarine” character look, and I use it quite a bit in my drawings. Or I mean to say I dress how I draw myself. I usually do the drawings first then find a way to make my clothes match.
You’re assuming I wear blue jeans. None of that for me, khakis, cargos, and cords all the way. (jeans are just too damn stiff and tight, even the loosets most broken in ones I can find seem too constricting for my taste.)
I like my blue jeans a nice indigo colour. I prefer them stiff, tight, and bootleg (I can wear boots to make myself taller! Yippee!). I also like them with a small waist so I don’t have to wear a belt.
Long enough.
And low-waisted. The waist band on regular jeans digs into my rib cage. I’m proportioned wierd, I guess.
I like mine from structure, Light or dark blue, carpenters style, wide leg, with the faded look on the tops of the thighs, with some contrasting threads that make for a neat almost like a plaid pattern. They should also be fitting, but not tight.
Flare legs is all I’ll wear. I like the low cut, but I haven’t bought a pair yet. Straight leg jeans make my butt look big.
I like’em a little to big and a little too long. Once they start to deteriorate (in places other than the heel area) I get rid of them. My favorite pair of jeans are over 2 years old and wore often and still don’t look like they are over 3 months old or so.
The best jeans that I have come across are from L.L. Bean They fit just right, last a good long time, don’t fade out too fast but fade nicely and I swear by them. They have the perfect size for me (35w x 34l) and are not too expensive - $30.00/pair. Highly Highly Recommended. Way better than Levi’s, Gap, J.Crew, etc…
Psst… Chrome Spot, it’s Graham, not Gram. I am currently wearing Gap painter’s blue jeans. I like them because they’re roomy.
Levi’s 505, boot cut.
You find them everywhere, they last forever, and they come in my size off the rack - 29x34
I like my jeans either very dark or very faded - no stonewashed for me. They have to be low-waisted, and snug around the butt, 'cause I have a nice butt. And boot-leg, but not flared. I can’t stand pegged-looking jeans.