The one thing that annoys me about these lack of descriptors on 'oversized' items is it begs the question... 'oversized for whom?'

What about plus sized folk, who need a 45+ inch bust for a tailored fit? Or a tall person, on whom 25"+ sleeves don't even reach their thumbs?? I do a lot of my shopping online these days, where listing these sorts of measurements really matters...

The closest 'oversized' blazer I have hits well past my hips & wrists - part of an (obviously not modern!) wool pantsuit. It's probably the closest I'll get because the shoulder pads(!) help the fit to look intentional (instead of 'drooping' dropped shoulders). 'Sartorial drowning' is always a risk for us petite folk

Brooklyn, I think you put your finger on why I’m loving my parachute pants! They fit nicely at the waist and high hip and then just float down the rest of my legs, camouflaging the heaviest part of me in a way that looks intentional yet chill. After so many years of skinnies, I’m loving a little bit of oversized in pants.

Sorry I have not read all the responses but did want to chime in because I have a number of "oversized" blazers. It's all in the proportions for me. First and OS blazer must still fit in the shoulders and the sleeves should be tapered and hit at your preferred point. The body should be straight but the stance should be lower with one or two buttons ideally so it can be worn open, or closed like a blazer dress. Material needs to have some substance but not be stiff. I always do OS with lean - so leggings, skinnies, monochrome, maybe with a scoop neck for turned back or 3/4 sleeve to provide structure, tunics with hip belts for structure and underlayers should be similar in length to blazer, long tunics, mini skirts or dresses with leggings or tights with a great bootie or boot is flattering and comfortable. I will wear a shift dress or tunic but only with leggings or tights, long over lean rules for me. Again pants for me skinnies only for contrast. It's really all in the mix or fit and no one size never fits all but it's a look I really enjoy but I'm always careful about fit, color, proportion.

Nope, not a fan.