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Not having much luck with a few 100% cotton bandannas. I tried what online sources recommended such as baking soda and vinegar in various combinations of washing and also I dry them in a dryer to soften.

But they are still very stiff when dry. I wet them to wear and that makes it a little more comfy. I looked at Amazon question and answer for this product and someone tried soaking in fabric softener but he said it took 50 washes to soften.

Maybe I will just have to wait until it get washed 50 times. Any ideas?

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Cotton's 'softness' is prescribed by which cotton they use to it weave from. The only way to soften up 'tough-as-old-boots/scratchy-as-nails' cotton is to thrash it until it loses a lot of its original fibre content.
This way, it will become just about 'perfect' just before it falls through to holes ;)

You will find a myriad DIY methods to soften up 'hard' cotton. Most of them are truly useless. Bicarb, vinegar, bicarb and vinegar [try to figure out the logic of that one], salt, home-made fabric softeners with hair conditioner…

Once it's been through the first few machine washes, any structural component provided by starch & dye residue will no longer be a factor - what you're left with is cheap, stiff cotton.
The only way to deal with that is mechanical abrasion.

You could stonewash… but that's really not good on your washing machine. Maybe you could use a cement mixer & a shovel-full of hardcore if you happen to work in the building trade.

I think your only real domestic option is 'dryer balls' [the 'free' alternative to which is a pair of clean trainers].

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which will [slightly] increase the abrasion during drying. They do provide a little loft to fabrics, but they won't really soften a hard cotton in a couple of washes.

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  • Interesting answer. If mechanical flexing or abrasion is the way to go, not chemicals, perhaps leave the cotton garment on a line to flap in the wind for two weeks, against itself. Or against a few small rocks also suspended from the line to collide with. Commented Jun 12, 2023 at 22:27
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    @Tetsujin Thank you for clearing that up. Most gracious of you. What you are saying makes sense. The bottom line is that if the cotton is not already soft your gonna have a problem because by the time you wash it enough time to make it soft it will be about time to scrap it for a cleaning rag. I think the moral of the story is that when you shop for a bandanna please be smarter than I was and buy one that is already soft.
    – Sedumjoy
    Commented Jun 13, 2023 at 13:25

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