This YouTube video covers it pretty well. Part of a trend away from suspenders and using less fabric changed mens style to low waist, along with people coming back from war thinking the uniforms were more practical.
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Sometimes. For example if I'm out shoveling snow I'd rather not get snow in my asscrack, so I wear my pants higher.
It depends on how the pants are designed. Some are high-waisted pants and can't really be worn low on the hips.
Sure. Depending on the cut and styles, it can be very comfy. Most of my jeans are cut where I have plenty of crotch room when worn at the waist, so I can do my thing without them sliding and still have plenty of jiggle space.
It took me until this year to accept that my waist is where it actually is instead of lower. My body just isn't shaped like that. Yes, sometimes I do wear pants actually at my waist, generally along with suspenders.