The second weekend of the Jazz Age Lawn Party is taking place in Governor's Island this August 13th and August 14th. During the first weekend of the 11th annual JALP, Junior Baby Hatter spotted a mashup of hat trends from the golden era of jazz up to the swinging thirties and forties. From flat caps to fedoras, here’s a little hat inspiration, and history lesson, if you’re looking to top off your twenties themed costume.

Flat Cap | Rounded cap with a small stiff brim in front

This oldie-but-goodie dates back to England in the Elizabethan Era when hats were required dress code for all common men over the age of 6 by the law. These hats were introduced to American fashion through Ellis Island by English and Irish Immigrants in the early 1900’s and later worn by taxicab drivers with two snaps under the bill to tuck their work tickets. This style of hat is formal without looking too pretentious.

Bowler | Hard felt hat with a rounded crown

Bowlers were created in the late 1800’s for gamekeeper’s to protect their noggins from branches while horseback riding and later worn by 21st century icon Winston Churchill. This hat is just plain dope. Definitely a good choice if want to look like old money from a F. Scott Fitzgerald novel.

Boater | Summer hat made of sennit straw and grosgrain ribbon

These hats wear inspired by Venetian gondoliers and later made popular by Princeton Ivy League students. If you are going for a preppy look, go with a boater hat.

Fedora | Creased, soft brimmed hat

1940’s Hollywood icon, Humphrey Bogart’s tough-guy charm branded fedoras as the go to hat for the strong silent types. Fedoras are good choice is you are going for effortlessly cool.

Cloche | Deep, bell-shaped crown and narrow brim hat

French for bell, the Cloche hat was designed in 1908 by a French milliner. It hit it’s height in popularity during the roaring twenties as the iconic look of flappers with bobbed haircuts.

Custom made Linen Cloche by Lisa McFadden.

Markisha Velazquez is the designer and owner of Junior Baby Hatter, based in Weehawken, NJ. When she’s not making dapper caps for babies and toddlers she commutes to New York with her family and blogs about her adventures in the city.