Half a Sixpence [1967 - UK] musical

As a young boy, Arthur Kipps becomes an orphan and is entrusted to a miserly shopkeeper who caters in ladies' fashion but keeps his knavish staff in Dickensian poverty. Arthur grows into a slick womanizing salesman, able to secure dates but utterly lacking the self-confidence to aspire proper relationships, feeling 'unworthy' of young ladies. That changes when his grandfather's testament leaves him a home and yearly income worthy of a proper gentleman. After diving into theater, London nightlife and traveling the world, he returns, missing his friends, and seeking his way into society, despite his utter lack of upper class education. As winner of the regatta the fancy Walsingham family sponsors, he is engaged to their posh daughter. However his childhood first love Ann, now a maid, turns up to scold his engagement, which he ultimately breaks because they socialites treat Ann badly. They get married instead, but her unwillingness to 'rise up in society' with him causes ever more tension, and financial trouble lurks.