Then & Now – Celebrities in Hats

Some people grow up loving hats, whereas some fall in love with them later in life. We’ll take a look at celebrities who wore hats as a little one as well as an adult.

Frank Sinatra

Frank Sinatra

Young Frank. Old Frank. They’re basically the same suave gentleman in a fedora.

Drake

Drake

Looks like snapbacks have always been a favorite for Drake.

Leonardo DiCaprio

From child star to movie star, Leonardo DiCaprio is one classy dude.

From a child star in a western hat to a movie star in flat caps, Leonardo DiCaprio is one classy dude.

Orlando Bloom

Beanies may just be Orlando Bloom's favorite style of hat.

Beanies may just be Orlando Bloom’s favorite style of hat.

Britney Spears

From performing to judging, Britney Spears knows how to rock a wool felt hat.

From performing to judging, Britney Spears knows how to rock a wool felt hat.

Jessica Alba

Jessica Alba

From a casual backwards ball cap to a sophisticated straw fedora, Jessica Alba always looks good.

Lea Michele

From Broadway to the small screen, Lea Michele is quite the entertainer.

From Broadway to the small screen, Lea Michele is quite the entertainer in both newsboys and berets.