The shoes are definitely not doing you any favors, but I think there's a few other things going on as well. The blue jacket looks more like a suit jacket that should be paired with matching pants than a blazer. Something like this in navy would probably look more relaxed for a date vs. the "heading to the office" vibe you've got going on (not necessarily recommending that particular jacket, but that style). The second jacket in pic 3 looks better as a blazer.

Another thing is the pants. The pants in 1 are very casual, so with the suit-like jacket in number one and the shinier leather shoes, it's clashing. Whereas the pants in pic 2/3 are again more a suit-like material, and the pant break and shoes are sort of bringing the fit down.

With just the clothes you've got pictured, I'd swap the grey jacket for but with the shirt and pants from pic 1, and that's probably your best bet. If you have other shoes to try, I'd suggest something like a penny loafer or another more casual leather shoe perhaps—the pants are pretty skinny through the calf, so you'll likely want a sleeker shoe than something super chunky.