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.

I know this is a bit old but I have some more thoughts
I appreciate gryffin’s specific fit notes, and tend to agree the reason mine feels slightly off at times is probably the shoulder fit. I did initially also assume that I’d be wearing it only with slim pants, but as I posted a while ago Carol S inspired me to try mine with wider, longer jeans (not dramatically wide but definitely not skinny or even straight, and no ankle showing), and I enjoy the effect very much.
Fashion trend images tend to come at us first from a very specific angle - as worn on tall, slim, young women. And that can imprint us with specific ideas about what works - ideas that aren’t necessarily true. The skill (and fun!) is in figuring out how to make those looks that appeal work for the individual. I love that we have access to a much larger range of images these days, via social media and brands diversifying their models. I’m not a slim person in general, yet I’ve always loved oversized clothes. It started when I was a preteen with a rapidly changing body that I didn’t want to show to the world, and some 80s fashions that weren’t about being sexy or body con or whatever you want to call it. I’m not ashamed of my middle aged body, so it’s no longer a matter of ‘hiding’, but I also don’t feel the need to slim myself down visually. Simply rolling up the sleeves of my blazer reduces the visual overwhelm factor and makes me quite happy.

The true OS blazer is not for me either. As Griffin said, these blazers could be best paired to skinny bottoms-which I don't do nowadays. But, I love a blazer with great shoulders, a looser fit and longer length! This will fit me sometimes fluid (with ease) because am tall, long torso and have wide shoulders-and is a great alternative to the tailored/structured ones I have---but am not thin (nor young:-)) anymore- so my body takes up space-and I have to watch close for the optimal proportions on me.

I find in general it is harder to combine an oversized item with a slim bottoms and get the proportions right.

I feel punked. I read the whole thing pondering my own response, then realized I *did* reply, 2 months ago! Well at least my opinion has stayed the same