During the 1920s, men’s fashions tended toward loose-fitting garments–baggy, high-waisted zoot suit with a watch chain dangling to the knee. Long, often double-breasted, jackets featured massive shoulder pads. A fedora completed the ensemble. Then came the stock market crash and years of hard times.
Fashion for both men and women switched to skinnier garments requiring less fabric. Suit jackets still had wide lapels that extended almost to the belt line and had padded broad shoulders. Trousers still had wide legs, but not nearly as wide as zoot suits. They had cuffs and center creases with a narrow waist set as much as three inches above the navel. Hats remained essential and men wore a lot of wingtips.
The first polo shirts came out during the thirties, as did Indiana Jones style Bush shirts with four patch pockets. Sweaters and short jackets came out during those years as well.
Since Jack and Bobbi spend a lot of time swimming, I spent some time looking at swimsuits. Men’s swim trunks without tops also came out during those years–as well as women’s two-piece swimsuits. For Bobbi’s work clothes, click here.
For Jack, I found some thirties-era casual ensembles.
I think Tony would have worn suits the times he spent with Bobbi–except the first time they met on the street near Bobbi’s apartment.