I feel like caseless people just are less clumsy than me. Heck, last week I somehow misjudged where the door access pad was at work and ended up knocking my phone out of my hand and onto the concrete below. Thankfully my Otterbox Defender took a slight scuff but phone is pristine.
I can only speak for myself, but as a caseless person I am clumsy. I have just adapted and reprogrammed myself in a number of ways that are simply just a hassle (it seems to me) for most case users. That isn't to say I don't drop my phones because that still happens. It's just much rarer now and has rarely resulted in any damage.
I learned spatial awareness. I.e., where my phone is in relation to my body/hand and objects around me in space. I don't pull my phone out in crowds, I don't use it one-handed. I have places I set my phone down based on where I am and what I am doing and I discipline myself to put it there every time. If I have to have my phone out in crowds I will use my hands to 'cage' it so that my hands are protecting the device.
I have older phones for use when I think my primary phone might be damaged. For instance, I go on walks with my 6s Plus and not my 11 Pro Max. If something happens it won't happen to my 11 PM because it's not there. I have a 6 Plus as well that is unlocked that I can swap a SIM card in to.
All of this stuff just becomes second nature with practice. Benadryl and other antihistamines have unfortunately affected me twice. Being under their drowsy effect caused two drops sufficient to require repair/replacement. I was simply just too drowsy to hold my normal attention.
I’ve also got kids that drop things regularly. Youngest dropped his phone 3 times within 5 minutes yesterday. And my oldest will destroy his case as he fidgets with it - Otterbox replaces it for a $10 shipping/handling fee. Otterbox lifetime replacement is amazing for those of us with autistic kids.
My son has always been careful with his stuff. He's 19 now and has used three phones since he was 15, all without cases and undamaged. The first was a 4s, the second an SE and his current phone is the SE2.
My daughter is an entirely different matter. She's trashed both the iPhone 5 and the iPhone 6s that were my wife's phones before she got them. I got her a new SE2 last year and I put it in an Ottorbox Defender. When she is paying for it I won't care, but this is my investment and I can't force her to start caring so she has to suck it up that it's in a case (she doesn't like it). She drops stuff not because she is clumsy, but because she just doesn't care enough to pay any attention at all to what she is doing.
My wife uses cases because she doesn't want the hassle of what I do.
I wish I could be a caseless person because I would LOVE to show off the pretty green phone on its way to me but I need it to be functional more than pretty.
Everyone has their own reasons for going caseless or not. I'd use a case or a beater iPhone if my occupation was different. But basically I sit in front of a computer all day and the most time I spend outside the house is tops 3 hours - and that's driving people around.
My kids are 19 and 15, so not so much a concern now as it might have been 10 years ago.