This Star Trek: Deep Space Nine photo contains
fedora, felt hat, homburg, stetson, and trilby.
There might also be
concert, boater, leghorn, panama, panama hat, sailor, skimmer, and straw hat.
This touching montage was the last we saw on screen of many of the DS9 regular characters as they parted ways in the series finale "What you Leave Behind" which aired June 2, 1999.