It’s not always so simple. 
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CROP Kentucky Derby Porch Party
Credit: CREDIT: HECTOR MANUEL SANCHEZ; STYLING: RACHAEL BURROW; FLORAL DESIGN: JUNIPER AND JASMINE

It's not everyday that you find yourself discussing the nitty-gritty of hat etiquette. However, there are moments when it becomes relevant, such as when you're about to walk into a wedding or when you're attending a religious service. While etiquette in general has evolved greatly over the course of generations and has become much more fluid than rigid in recent years, many of the rules are still observed today, especially in the South, no matter if the rules are tweaked to fit a modern situation. 

For instance, hat etiquette is still widely upheld. Etiquette stickler or not, it can be helpful to know the basics before breaking out the wide-brim. Firstly, manners around headwear go back many, many years. According to the Emily Post Institute, many trace it back to medieval times when knights would remove their helmets to identify themselves, as well as a gesture of respect. Hat etiquette also has roots in Christianity, as it's long been considered customary for men to remove their hats upon entering a church. As we all know, however, church hats are a historic tradition for women to wear in the South. Per church hat etiquette, women are allowed to keep their dress hats on in church, unless blocking anyone's view during a wedding or baptism. The more you know! 

Additionally, there are rules put forth by the U.S. Flag Code. For example, men—not including those in military service uniform—are supposed to remove all hats during the National Anthem, as well as during the pledge of allegiance. Women are not required to remove dress hats. The same goes for when a United States flag passes by during a parade. The U.S. Flag Code is not upheld by law, but is rather an advisory. 

CROP Kentucky Derby Porch Party
Credit: CREDIT: HECTOR MANUEL SANCHEZ; STYLING: RACHAEL BURROW; FLORAL DESIGN: JUNIPER AND JASMINE

Historically, men's hat etiquette has designated that all hats should be removed upon entering indoors, which includes houses of worship (unless customary otherwise like at Jewish synagogues), public buildings, and private homes, especially at mealtimes. Exceptions include when attending indoor athletic events, taking public transportation, or traversing public thoroughfare spaces such as airports, hotel lobbies, and elevators. 

Historically, women's hat etiquette has designated that dress hats are allowed to be kept on indoors including at someone's home, during a religious service, and at weddings, except when blocking anyone's view. (Technically, baseball caps are still supposed to be removed indoors and during the National Anthem for both women and men.)

All in all, hat etiquette comes down to what some view as proper or polite, but just as with any other etiquette discussion, these hat rules can be subjective in different situations and depending on different people, cultures, and beliefs. There's at least one thing Emily Post could never deny: Hats are always welcome at the Kentucky Derby. The bigger, the better.