midi pinafore dress Gray Wool with Adjustable Waist and Pleats – YLISTYLE Styled with the Ballet Jersey T Valar Lace Up Midi Pinafore
Description
Yes, usually

Tailored Chinos + Button-Down Shirt + Blazer : Combine a pair of beige tailored chinos with a crisp sky-blue Bengal stripe button-down collar shirt and a navy tailored blazer made with a lightweight textured summer wool, linen, tweed, or flannel depending on the season

There are shops specializing in authentic vintage but it is difficult to find an original 1920 dress in good condition and that does not weigh too much

Dads and sons can wear tweed jackets or cozy knit sweater with trousers or jeans