In the early days of baseball, teams would compete all season long for the right to claim the pennant, which was the triangular flag that would fly over the champion’s home field. When smaller felt or cloth versions of these pennants were offered for sale or given away as souvenirs, fans snapped them up.

Vintage pre-World War II pennants are tougher to come by than ones from the 1950s and ’60s. Examples of these early pennants include the screen-printed pennants from the 1910s featuring the image of a player batting or pitching alongside a single word that says it all—“Brooklyn” or “Giants.”

Especially collectible are pennants from the pre-curse era of the Boston Red Sox, when a slugger named Babe Ruth pitched for the team. Similarly, pennants from the pre-Black Sox ...

Picking up a pennant at a ballpark was not the only way to acquire one. In the 1930s, the Red Ball candy company gave away mini-pennants (2 ½ by 4 ½ inches) with its products, and in the 1950s and 1960s, Bazooka sent fans a free pennant of their favorite team in exchange for bubble-gum wrappers. In both cases, the souvenir pennant was used to drive sales.

Some of the most graphically interesting pennants from the mid-20th century are the ones in which a winning team’s roster has been printed alongside an image of its smiling mascot or an iconic player. The Los Angeles Dodgers pennant of 1959 is especially noteworthy because in addition to a roster, it also depicts the Los Angeles Coliseum, which was the temporary home of the Dodgers before they moved across town into Chavez Ravine.

A variation of the roster pennant, popular in the 1960s, was the picture pennant, which included an actual photograph of the team stitched or glued into the wide end of the pennant. Because paper ages more quickly and is less flexible than felt, these picture pennant are tough to find in mint condition, making them a bit more collectible than other vintage pennants from this decade.

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