Dressing for the Kentucky Derby is arguably one of the trickiest fashion endeavors of the year. For ladies on Halloween, if the packaging said ‘sexy’ and it was totally inappropriate for the weather, you probably nailed it. New Year’s Eve- Did the outfit sparkle while being totally inappropriate for the weather? Yes? Good, your fashion cred remains intact. But for Derby? Welcome to the big leagues of fashion ingenuity. From weather and rules to accessories and hats (for both men and women), we are going to attempt to cover the gamut of things to consider when dressing for this most momentous of days.

First know this: the weather never cooperates on Derby Day. Never. The first Saturday in May always seems to be a day when the seasons are duking it out to the peril of everyone outdoors. Spring is all, ‘You guys! This is my time!!!” Summer is all, “But I’m impatient! What if I just sneak in a few rays of sweltering sunshine intermittently throughout the day??” And Winter is like, “But I don’t wanna go! I still have some stuff left! <looks around, digs in the couch cushions> like this hail! Here! Have some hail!” If it hasn’t just rained, turning the infield into a pit of mud, rest assured, it will in just a moment. The wind will blow, making you freeze. The sun will poke through, making you sweat. It is basically a barometric free-for-all. Dress accordingly.

Oh, and umbrellas are NOT allowed. Security will look in your bag and they will make you leave your umbrella in an unattended pile at the front. Your umbrella will have disappeared by the time you come back for it, if you even remember to do so. Other things you not allowed to bring in include camcorders, coolers, and booze. Now we at PorchDrinking are certainly not encouraging anyone to break any rules, but we do feel it is important that you know that apparel enhancements like this and this exist. Do with that information what you will.

Your actual outfit should also take into account where you will be at the Derby. Locations range in price and fancy factor from the Infield to Millionaires Row. The infield is mostly locals and people who go to Derby too often to care about spending more than the cost of general admission ($40). Jeans and flip flops are totally acceptable. The infield is also the muddiest spot should the weather be wet so either wear or bring extra shoes that you don’t mind getting caked in mud. A step up from the infield is the Infield Club, which has nicer porta-potties and some actual seating. A nice summer dress and cardigan or slacks and something with a collar will fit in just fine here. If you have tickets for the grandstand, well don’t hold back! Get fancy! Millionaires row? You are dressing for the cameras now, but you already know that. Ladies, you know that fancy dress that’s really too fancy for most events? Wear that. Excessive fringe, lace, and hemlines can all fit in at Derby. Fellas? Consider a bow tie. Bow ties are cool. My number one recommendation is this: Aside from certain restrictions, wear whatever you damn well want. This is Derby and all are accepted here.

But don’t forget your hat.

For the love of Seattle Slew, do not forget a hat.

You can opt for the more traditional large-brimmed and elaborately decorated hats such as these. Or perhaps something more modern is more your thing, like this assortment from the Savage Millinery. Or you can become beloved by all you encounter by doning something like this across your noggin:

Pro tip: all the best and craziest hats, will almost certainly be found in the infield.

I will say this. Choose your hat and its decorations wisely. I have attended Derby twice, in 2009 and 2010. Both years, I wore a simple, white, wide-brimmed hat, which I decorated with real roses (it is the run for the roses, you know) that I got last minute from the discount bin at the grocery store. Both years, I placed bets based on the color of the roses in my hat, as corresponds to the colors of the horse positions. Both years, I won. It’s not superstition. It’s not magic. It’s Derby.