Thoroughbred horse breeders and the landed gentry have attended the Kentucky Derby since the premiere event in 1875. While the race itself is short—they do call it the “Greatest Two Minutes in Sports,” after all—the traditions are well established and rich with local color.  One tradition that has stayed with the festival throughout the years is that of sporting the perfect Derby hat. San Francisco based milliners Goorin Bros. is a century-old family-run business that just launched a ready-to-wear line of Kentucky Derby hats. Along with their expert help, we’ve put together a guide to assembling the perfect Derby look.

1. If you want to sit in the stands—or better yet, in Millionaires Row—you’ll have to dress the part. Save your shorts and T-shirt for the infield. It’s usually warm on Derby Day so women will be seen in sleek summery dresses and wide-brimmed hats, and men in lightweight suits complete with bowtie and walking stick. And of course, almost everyone will be punctuating his or her look with the perfect hat.

2. Before you start your hat shopping, you need to get the right fit. Place a measuring tape or a piece of string (that you can then hold up to a measuring tape), around your head 1/8" above the top of your ear and across the middle of your forehead, exactly where the hat will sit. If you fall between two sizes, always opt for the larger size to avoid tightness.

3. Men sporting pastel seersucker, broad patterned gingham shirts and off-white nubucks can complete that classic look with a range of summer straw hats. The two basic styles for race-goers are the fedora and the boater, which you can personalize with bands and feathers.

4. Goorin Bros. say, “If you’re going for a cleaner look, the Churchill straw fedora is a classic hat with a lack of embellishments that keeps the wearer looking fresh. The Pierre Renoir straw boater, also known as a skimmer, is another classic. With an iconic shape reminiscent of sailing and quartets, this hat offers a lot of unique styling options. The gentleman wearing the Churchill is probably pairing his hat with a sophisticated suit. On the other hand, the guy in the Pierre Renoir is at Derby festivities partying in style wearing a pair of linen or khaki pants, suspenders, a crisp white button-down shirt, and patterned bow tie.”

5. Women will be wearing summery frocks running the gamut from couture Oscar de la Renta to off-the-rack J. Crew. Shoes and hats are the focal points for women’s Derby outfits. “For women, a straw floppy sun hat is almost the standard hat of choice since its shape is synonymous with Kentucky Derby fashion. The Mrs. Perfecta straw floppy hat is the perfect shade-induced topper and has feminine qualities like its rich red palette and hand tied polka dot bow. However, we wouldn’t shy away from choosing a bell-shaped cloche hat to stand out amongst a crowd of wide brims. The In The Money cloche is made of a packable ribbon straw with a sweet polka dot floral accessory. Both styles can be dressed up in a summer dress or bold separates.”

6. Goorin Bros.’ ready-to-wear hats are found in boutiques in cities across the US. If you want something unique, they have experienced haberdashers and milliners on hand to custom design and fit any hat to your style in their flagship shop located in San Francisco’s North Beach neighborhood. 

All images courtesy of Goorin Bros.