If you're looking to strike a balance between conservative, cute, and comfortable for you day to day wear have you considered the charming and coy influences of the chic 50's school girl?
Simple pieces with simple embellishments add just enough allure to make this look attract attention. A coat with toggles has a somewhat vintage vibe while a skirt with a scalloped hem has a sweet appeal. You can never go wrong with a standard cable knit sweater and cat eye glasses are an enchanting extra. Modernize your loafer with a wedge and highlight a lady like dress with a patterned lady like pump.