The Top Hatters were activated as VF-1 in 1919 and are the Navy's oldest continuously active squadron. In 1942 it was designated VS-41 and flew SBD-3 Dauntless torpedo bombers from USS Ranger in the North African Theater of Operations. In November 1943 it was redesignated VB-4 flying the SBD-5 Dauntless against German forces in Norway.

The squadron was transferred to the Pacific Theatre in late 1944 where its pilots flew SB2C Helldivers from USS Bunker Hill in the island hopping campaign through the central Pacific. The Top Hatters ended their WWII combat flying from USS Essex in action over Iwo Jima, Tokyo and Okinawa.

A famous incident occurred when Top Hatter pilot Lt. Paul Pablo encountered a swarm of Japanese fighters over the Bonin Islands. Lt. Pablo was not heard from again, but his last radio transmission was, "I've already got four, and I've got 30 cornered."

The squadron was redesignated VA-1A in November 1946, VA-14 in August 1948, and VF-14 in December 1949.

The Top Hatters have also seen action in the Vietnam War, the invasion of Granada, air strikes on Lebanon, Operation Desert Storm, and sorties over the Yugoslavia.

The top hat on the squadron patch has changed over the years, but this patch design was used on squadron patches during World War II.