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You're doing it correctly, right? Right-clicking on the item in the main inventory panel (not the subpanel for that piece of armor) and going from there?
Have you finished assassinating the Wolf of Sparta for your first big job? It might be tied to that.
When you play again in Game+ you won't have that problem. I had a great time in my first Game+ playthrough, where I could tackle the map in any order I wanted and decided not to use fast travel but travel everywhere by horse/boat/foot.