Thank you for all the opinions, everyone! They really helped.
I ended up wearing the shoes today, and I really like them. I do not like pointy toes and don't find them comfy, so holding out for that is not an option, no matter how trendy they are. I am going to use these to add some polish, since that is what I need to up the ante on to bring my style to work.
I'll hang onto the jacket for now and see if I wear it casually. I didn't say before, but the shoulders feel a little too strong with my super short hair, and that is why I feel iffy about it. Maybe I'll feel different when it grows some...