Great outfit, the silhouette is flattering (slim jeans, layered tops). Overall it has a edgy look to it which is who you are. So I approve. I am really surprised your paralegal didn't like the outfit. It could be he was just having fun with you. Or, the look is too new for him/Alaska. To me there is something sexy about skinny jeans and boots so maybe that threw him a little too.
I get that from guys around here too. But when men comment on my outfit it never hurts, because their comments usually betray their lack of fashion expertise. A comment from a stylish woman though is different. I could stew about something like that for days. And have.