1
first, soak the headband or ponytail holder in a bit of oil. this will help loosen the elastic bonds a little. Afterwards, stretch the band before you begin wearing it. try wrapping it around a chair back or something wide enough to give a good stretch so that by the time you wear it, it won’t be too snug & give you a headache!
2
instead of using the usual headband or ponytail holder, many have gotten creative & use a shoelace, a long satin/silk scarf or even cut-up piece of pantyhose. using these items will help you control the tightness & amount of tension being put on your head/head. plus, the materials are non-drying & hair-friendly.
3
you can still be at risk for breakage if you is in need of moisture. dry hair is already more likely to break. once tension is put on it, even worse. moisturizing the hair well (water-based first, then oil or butter) will create a nice barrier & slip to lessen friction on the hair & prevent breakage.