classic dresses Blue Gingham Spaghetti Strap Swing Dress – Unique Vintage Classic Shirtwaist Dress in Navy

Adding legwear is a great trick to offset the length of your borderline "too short for work" dresses

No A-I No-AI Material Main - Weighty Silky Satin Lining - Stretch Satin Lining - Stretch Satin Stretch Factor: Some Stretch WHERE TO WEAR Black tie events, special dinner plans, candle-lit date nights, cocktail nights with girls, vacation evenings, glamorous celebrations

If hes doing it, take that as a green light

You could create your own early 1920s silent movie character outfit with a mix of long dresses (lace, light sequins, silk), headscarves or turbans, layers of jewelry, scarves as waistbands/skirts, and greyscale makeup