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I believe the classic advice is that your clothing should get longer as the layers add up - shirt, suit, overcoat/other long coat. Throwing a puffer vest atop a suit jacket ruins a good bit of the initial attraction of a suit, methinks.
Would it be OK if the down vest is worn with a SC instead of a suit. I think in the pic in the OP the vest is worn over a SC and jeans.
Don't do it, i'm surprised someone hasn't been shot for this.
i think vest over the suit looks great. i have penfield vest that i wear over my flannel suits when its cold and it looks great. also the majority of my trips to milan and florence in the winter i've seen this look by the italians. though the ones they have have breast pockets. thank goodness i havn't seen a pocket square in one of them though. HA
Italians have been doing this for years, wearing down vests/ padded gilets/ bodywarmers over suit coats/jackets.
Please elaborate; what part of the outfit (shirt, sweater, single breasted 2 button suit, brown belt, matching boots, and fitted cream-colored puffer jacket) exactly screams "homeless guy?" It certainly isn't the most elegant look, not by far. But as others have agreed, a young person could pull it off while still being worlds apart sartorially from his peers.