13 Dos and Don'ts for Surviving a Rainy and Cold Kentucky Oaks and Derby

Gentle readers, I must admit that my first instinct is to tell you to stay home.  To tell you that if you have spent a small fortune on tickets to the Kentucky Oaks and Kentucky Derby as a Christmas gift for your in-laws who have lived in Kentucky for most of their lives but have never been to the Derby but then you find out that the entire weekend is going to be cold and rainy, you should just cut your losses and watch the whole thing from the comfort of your warm, snuggly couch. To tell you that the gorgeous hats you've purchased to wear with your lovely dresses and perfect shoes will wait until next year.

Of course, that's not what we did at all.  We instead braved the 47 degree temperatures and constant downpours because doggone-it we'd been waiting for this experience since we bought the tickets last August.  We'd prepped and planned and primped and we were going darnit.

In spite of our pleasant expressions in this shot (which we took as soon as we arrived and after which we all bundled up as much as possible), we were cold and damp most of the day on Friday at the Oaks.

Derby Day was much more pleasant with warmer temperatures, intermittent rain, and occasional sun.

The last time we went, I wrote a Derby Dos and Don'ts post, and I must say that I'm going to have to eat some of my words when it comes to surviving the Oaks and Derby in the dreary, drizzly damp and cold.  I guess my judginess is adaptable.  I've decided to frame that as a positive character trait.

The pictures in this post are from both the Oaks on Friday and the Derby on Saturday.  OK.  Here we go.

Derby Don't #1 comes straight from my precious father-in-law, Steve.  Don't wear a hat under your hat, especially when one of them is a maroon toboggan and one is a straw fedora. (Well, unless it's 47 degrees and rainy.  You won't be a fashionista, but you'll be more comfortable than those of us who are more vain.)

Steve carries a blanket while waiting for the shuttle at the Kentucky Exposition Center where we parked.

And this adorable picture of Steve brings me to Derby Do #1 for a rainy, cold Derby weekend.  Do bring blankets.  Steve is carrying the one he and Lanita brought, and Josh and I brought one of those cheap fleece throws that are ubiquitous as Christmas gifts. They roll up nicely into a fairly small bundle, so it fit into my bag relatively well.  I thought I would use it primarily for wrapping my completely-exposed-to-the-elements legs while at our seats, but we actually used it to sit on as well.  We hadn't brought seat cushions (which are allowed), and our metal bleacher seats were surprisingly chilly.  Sitting on the blanket helped keep us warmer, and as the day wore on, I did end up wrapping my legs in the blanket, too.                     

My toes aren't blue. but they are numb.

                                  

In spite of the chilly temps, Derby Don't #2 is a repeat from last time.  It's May, people.  Felt hats are not appropriate.  Felt = fall and winter, straw = spring and summer.  And I get that this year it feels like winter, but, alas, the calendar says May 5.  Put the felt back in the closet until November-ish, suck it up, and put on some spring straw.

                              

This lady clearly worked really hard on her outfit and would be a total DO if the Derby were in February.  But even a cute felt fascinator is still felt and thus only appropriate for winter.

                              

Derby Do #2 is whether you're a guy or a gal, do embrace color.  This is true for every Derby, but on a Derby Day when the weather isn't cooperating, you need all the color you can get to lift your spirits.  I know this may be hard for some of you dudes out there, especially those of you for whom just wearing a tie is a stretch, but this is really your chance to try out a colorful look.  Seersucker suits with pastel ties, pink pants with a navy linen blazer, a khaki suit with an Easter-egg-hued bowtie, even a little bit of a whimsical pattern on the trousers -- all of these brighten up a dreary day and are perfect for the Derby and Oaks.  Just look at the guys below who are not afraid to show some color.  I love it.

           

This yellow lace dress with its matching fascinator was faaaaabulous!

                        

A colorful hat with a winning smile brightens up even the dreariest Derby Day!

                       

Derby Don't #3 is a matter of modesty regardless of the sun's cooperation.  Don't let the girls out.  Like, even in warm weather, I don't want to see your sisters at the Oaks or Derby.  It's a horse race, not the beach.  And especially in the cold, your sisters probably don't want to come out.  Let them stay in.  Please, for the love of all that's holy, let them stay in.

Wowza.

                               

Can you say, "Cleavage?"

                               

I'm guessing he likes the view from his seat.

                               

 Derby Do #3, unfortunately, is do leave your umbrella at home.  Churchill Downs doesn't allow them, and they will be taken away at the entrance.  I didn't get a picture, but there was a HUGE pile of confiscated umbrellas at Gate 1, and I assume there were similar piles of contraband at every other gate.  I was hoping that a clear umbrella would be acceptable, but I left it at home when I read the list of items not permitted.

These signs were posted at the Kentucky Expo Center where we picked up the shuttle bus.

                                                                                                                                                                                                                                                                 

Derby Don't #4 is exclusively for rainy days.  Don't wear a poncho that isn't clear.  This is a sporting event, I know, but it's not the kind with a seventh inning stretch.  So bring a clear poncho.  You've probably spent a lot of time and money planning your outfit, and with a clear one, at least it can still be seen.

                              

                             

Normally, I would be saying, "Just suck it up and forego the poncho altogether because they're really just glorified trash bags that are cheap and flimsy and tacky and don't really keep that much water off anyway."  But that comment would be coming from someone who had never before experienced a Derby in the rain.  And now I have, so I fully embrace the clear poncho.  While my paternal grandmother always says that you have to suffer to be beautiful, it's just miserable to be wet and cold in a dress and heels for 10 hours.  I'll trade a little beauty to suffer a little less.

That said, if you have one, you should totally embrace my 4th rainy day Derby Do. Do wear a cute trench coat that matches or coordinates with your outfit.

I spotted this cutie patootie while hiding out in the ladies' room by the hand dryers where it was seriously 10 degrees warmer.  I wanted to just stay in there forever.  Isn't her little navy polka dot trench adorable?  She's a total Do.

Derby Don't #5 is another repeat from before.  Don't go on a craft store buying spree and then hot glue all of it to your hat.  You'll look like Michael's and JoAnn Fabrics had a baby that then puked on your head.  And this is from a girl who loves feathers and flowers and ribbon and vintage brooches and coils of sinamay!  I love them all!  But when they're all together on one hat they just make you look like a toddler playing dress up and piling on all her grandmother's accessories.

Flowers, and ribbon, and rhinestones, oh my!  And I'm pretty sure the lady in the right just bought one of those flower garland thingys and wrapped it around her head.  (And down her back.)

                         

I'm certainly not one to shy away from hat embellishments, but Lanita, Kelsey, and I prefer to put professional milliners in charge of our hats.

Derby Do #5 is a complete 180 from my last Derby post.  Before, I said that flip flops were only appropriate for giving your poor feet a rest while in your luxury box and were oh so tacky to wear while walking around.  But that was before I had sat in the bleacher area on a rainy day when everyone put their nasty, muddy feet on the seats to be able to see the horses run the Derby.  I brought my own never-worn gold flip-flops so that I could use them exclusively for standing on my seat without then having to sit back down on nasty shoe residue.  It worked out really well since later we decided to walk the two miles back to our car after the Derby rather than waiting more than TWO HOURS for the shuttle bus.  So here's my amended opinion.  Do take extra footwear.  And (I can't believe I'm writing this) even take rain boots if the weather is supposed to be nasty.  Both days I longed for the warmth and dryness of my Kate Spade rubber boots, but, alas, I hadn't brought them.  My old self would have turned up her nose at anyone wearing rain boots with a dress and hat, but after this year, I am only envious of those who knew better and came prepared.  Live and learn.

No muddy footprints on my bleacher seat thanks to the never-worn flip flops I tucked in my purse!

       

The disgusting results of muddy feet on bleachers.  Ew.

                                 

                 

A cute little trench and a pair of Wellies are perfect for a rainy Derby or Oaks Day.  I think I like her hat, too, though I can't quite decide for sure.  The color and the sculptural shape are cool, but it's pretty big, isn't it?

                           

Derby Don't #6 is even if Churchill Downs doesn't count it as contraband, don't wear an umbrella hat.  I mean, I can see the allure.  You're killing two birds with one stone, right?  You've got your hat and your rain gear all in one.  And MAYBE if you're in the infield where anything goes it makes sense.  But in line for the Longines Fashion Show?  Um, no.

This look is NOT going to win her a $10,000 Longines watch. 

                                         

Which brings me to Derby Do #6.  If you're there on Oaks Day, even a rainy one, do plan to walk in the Longines Pink Carpet Fashion Show.  Both times I've gone I have participated just for fun, and both times I got to meet interesting celebrities and people-watch some super stylish women (and some who just owned their not-so-stylish looks with confidence and verve).  And who knows?  Maybe you'll win the $10,000 Longines diamond watch!  It usually takes place inside Gate 10 at about 2:00.  You line up maybe a half an hour ahead, and they'll give you a little paddle with your number on it.  Then you walk the pink carpet, chat with the judges, and get your picture taken.  After everyone has walked, they announce a list of 10 call backs and choose a winner from those.  Because of the chill, Josh stood in line with me so that he could take my coat (my red Burberry raincoat, not a clear poncho) when it was my turn and snap a few pictures of me, too.  Bless his heart.  He stood there the whole time in the damp drizzle keeping me company.

Not quite a Glamour Do, but more like a Glamour Doing-the-Best-I-Can.  Plus I lucked out and found a pair of gloves stuffed into my pockets, so that was a big-time win.

                                         

My oh-so-dapper husband stood in the rain and cold with me for over an hour!

                                         

In 2014, I got to meet Carson Kressley and Simon Baker (you know, the mentalist?), and this year I got to meet Jill Goodacre (former Victoria's Secret model and wife of Harry Connick, Jr.) and Steffi Graf.  If you start watching the Longines video below at about 11:40, you'll see me talking to Jill Goodacre.  Every time I watch it, I'm surprised by how brief the conversation was - I walk out of the frame less than 30 seconds later - and by the way that I look all stooped over like a little old woman.  What was I thinking?  Stand up, girl!

 Here's basically what happened.  You first walk onto the carpet, and they photograph you holding up your number while standing beside a case that holds the $10,000 watch.  Then the guy standing there tells you to walk in front of the judges but that if they want to talk to you, they'll ask.  Well, I decided right then and there to ignore that part completely.  I was definitely going to take the opportunity to talk to Ms. Goodacre while I had the chance. After all, I'd spent the better part of my twenties making choices about what sleepwear, underwear, and swimwear to buy based on her photographs.  I certainly wasn't going to let a chance to talk to her pass me by.

 Anyway, I walked over (or perhaps wandered over like a little lost nursing home patient) and said hello.  Then I said, "OK, I have to ask you something.  I heard a rumor years ago that your husband sends you roses every single day.  Is that true?"  Harry Connick, Jr. has the reputation of being quite the hopeless romantic, and I wanted confirmation that the originator of the soundtrack of my college years was, in fact, as dreamy as I'd always thought.  She smiled and said, "Well, not every day but many days!"  Then I said, "Well, it's really nice to meet you.  I've admired you for years," or something else equally asinine to which she charmingly responded, "You're very sweet.  And you look lovely!"  Then comes the part in the video that, were it not there in full color, I would not believe really happened because I had blocked it out completely.  I start to walk away and then say something to all of them and make some sweeping hand gesture thing.  I have no idea what depths of stupidity I stooped to at that point.  Maybe I said something like, "I've admired you all!"  or "You all look great!"  or "Which way to the bathroom?!"  Who knows?  But after that, I continue my elderly-assisted-living-style walk across the carpet, not quite sure what to do next.  Nevertheless, I'd do it again if I were to ever go back on Oaks Day.  And you should, too.

                               

Jill Goodacre is seated on the left and Steffi Graf is on the far right.

Derby Don't #7 is don't dress as if you're going to the prom.  This is not a time to go all matchy-matchy with your date or to don your sparkliest cocktail dress.  You're not in high school, and no one is giving you a corsage.  It's a horse race, not a high school dance.

Without her gray sweater on, she is a DO... until her boyfriend walks up matching her.

                                

Again, she is a total DO...until he shows up beside her.

                                 

A full-length, gold-sequined jumpsuit would make you the envy of the twinkle-light-bedecked and teen-angst-filled high-school gym, but it's not the right look for the Derby.

                                                             

Derby Do #7 is do prepare yourself for copious amount of cigar and cigarette smoke.  I had actually forgotten about this part since last time, so it caught me off guard this time.  Man, do these people like to smoke.  I'm not sure what it is about the cigar thing, either, but it's not just men who are puffing away.  Women are, too.  Right next to you on a bleacher seat.  Like, less than 5 inches from my face.  Not fun.

Derby Don't #8 is don't wear a hat that is bigger than your torso.  (And the first girl below is a Double Don't because she paired her floral monstrosity with a white sequined cocktail dress.)  If people see you and think, "Is there a person under there?" your hat is too big.

Like, how did she get in the CAR to get here???!!!!

                                      

I mean, I love me some peacock feathers, but let's not put the whole peacock on our heads.

                                      

This one would make Dr. Seuss proud!

     

And an iridescent unicorn purse to boot...

   Derby Do #8  is do be cautious about buying your hat from a department store rather than a milliner.  The hat you see pictured below was worn by no fewer than EIGHT different ladies!  The pictures below represent only two of them, and those eight are just the ones I happened to see.  I'm betting there were more.  You may be wondering how I noticed eight matching hats in a sea of hats.  Well, it's because I bought the same hat!  I had thought about wearing it, but it ended up being uncomfortable and plus I like the one I found made by Chef Bizzaro Millinery much better.  So I took the one I had bought back to Nordstrom.  But, apparently, everyone shops at Nordstrom for pink hats.  Or, actually, this one pink hat.  Maybe it doesn't bother you to see other people dressed like you or wearing your hat, but I'd far prefer to have a one-of-a-kind creation made by a professional.                           

           

This lady has on the hat I almost chose for the Oaks.

                           

               

So does the lady on the right.

   

This lady does, too, though she's added a vintage brooch to it.

                     

And while we're on the subject of hats Derby Don't #9 is don't wrap your hat in plastic while it's still on your head.  You look like you're wearing a lampshade that's still in the packaging.  Either suck it up and wear the hat in the rain, or take off the hat and wrap it in plastic to protect it.  Don't do both at the same time.

                                     

                                       

And Derby Do #9 is, for heaven's sake. keep your hat on your own head, not your boyfriend's/husband's/date's.  That's just stupid.

I have no explanation for this weirdness.

I mean, I wanted to curl up in a coat and hide from the elements, too, but putting your hat on your boyfriend's head?  What?

Derby Don't #10 seems like a no-brainer, but apparently some people need to be told.  Don't wear your fishnets and corsets.  It's not a burlesque show, and while you might be channeling Dita von Teese, you look like a Derby Dominatrix.

Fishnets, feathers, and a feisty black corset are more suited to a night out in Vegas than a day at the Derby.

If you're a guy, Derby Do #10 is do wear seersucker, even in the rain.  It looks smashing and you won't be alone because lots of men wear it at the Derby.  Just don't wear a Bulls cap with it.

Kelsey and Steve are both DOs!  Steve bought this seersucker suit just for this occasion.

This guy would be a total DO if it weren't for that hat.

I'm hesitant about my next one because I SO get where she's coming from.  I mean, it was cold people.  My bare legs had me wishing I was in a Hillary-Clinton-type pantsuit all day long.  But I'm still going to have to say that Derby Don't #11 is don't wear black tights with your spring dress.

I know it's cold, but this is still a DON'T.

Of course, probably the most important thing to do to survive a wet and cold Oaks and Derby is Derby Do #11 - do shell out the cash for the covered seats.  I can't begin to tell you how much less miserable we were than the people who found themselves out in the rain for two days.  They would try to plant themselves in the covered seats of people who had gone to the betting windows or to the concession stands, hoping that they could stay there until the rain subsided.  We called those people squatters and were grateful to have our dry seats even if we were still miserably cold.  The obvious disadvantage, of course, is that you are farther from the track.  A less obvious disadvantage is that when everyone stands on their seats for the Derby,the slant of the roof means you can hardly see anything at all.  But that was all worth it to me to be able to stay dry.  And even if you're there on a sunny day, the covering will protect you from possible sunburn.  Spring for the covered seats.  We haven't regretted it either time.

We all particularly loved singing "My Old Kentucky Home" together before the Derby.  You can see in this picture how low the ceiling  was over our seats.

This was the tiny sliver that I could see while standing on my seat during the Derby.

Derby Don't #12 is don't mistake Derby Day for a 4th of July picnic.  Honey, I know that the most famous horse race in the US of A can give you a dose of good ole down home Kentucky-style patriotism, but leave your stars and stripes at home at least until Memorial Day.

Makes me want a hot dog and some sparklers.

Derby Do #12 is do take time to do some people watching - and listening.  Of course we saw lots of funny, strange, and interesting things....

I think this one is all three - funny, strange, and interesting.

Fake ivy garland and empty miniature Jim Beam bottles as hat embellishments would fall into the strange category, I think.

You'd think a sombrero would be one of the weirdest hats you'd see, but you'd be wrong.  The dude in the lower right has a cardboard model of Churchill Downs on his head.

People watching also lets you appreciate the people who completely nail the Derby and Oaks look.

...but we also heard some gems during the day.  My favorite came from a guy who, like us, was walking past the entrance to Millionaire's Row.  This is the area where the social elites, owners, celebrities, and corporate sponsors get to go, and peons like us who don't have the highly-coveted tickets and arm bands are left on the outside looking longingly.  As he watched the parade of who's whos marching confidently into the exclusive area, he muttered to his friend, "Peasantry sucks."  I have to agree with him.

Another memorable comment came from the sweet lady who drove our shuttle bus from the Kentucky Expo Center to Churchill Downs (and who was wearing a perfectly-appropriate-for-a-Derby-bus-driver horse hat on her head).  As we got off the shuttle, she said to us in her rural-Kentucky drawl, "I hope y'all all stay dry and purty."  (Translation: pretty.)  

If you're driving the shuttle bus, I think wearing a horse on your head on Derby Day is actually a DO.

Derby Don't #13 is, even in the rain and cold, don't wear running shoes with your dress and hat.  Even if they match.

Even the rain doesn't change my mind about this one.

And my 13th Derby Do is if you're going to have to go to the Derby or the Oaks on a cold and rainy day, be sure you have a friend like my mother-in-law's high school friend Deloris who let us stay in her lovely Louisville home where we could dry out and warm up while waiting for the sun to show itself.  On Derby Day, we relaxed in her luxurious kitchen eating the breakfast she had left for us while deciding whether we wanted to see all the day's races regardless of the rain or if we'd prefer to stay in the comfort of Deloris's home until the rain gave way to sunshine.  (We chose the latter.)  We wouldn't have had this option if we had followed our original plan and stayed 2 hours away at Steve and Lanita's in Ft. Thomas.  Being so close to Churchill Downs gave us flexibility and comfort in spite of the weather.  Plus, her home was elaborately themed for the occasion!

Horse-themed books and movies were on the tables in case we wanted to read or watch a movie, and a replica of the blanket of roses that is draped over every Derby-winning horse was in the entryway.

In the kitchen, napkins, plates, glasses, and even the displayed cookbook kept to the Derby theme.  Of course, fresh roses in silver mint julep cups were the flower of choice for the weekend since the Derby is also known as The Run for the Roses.

The themeing wasn't just limited to the indoors.  The porch was also decked in Derby decor.

I'm not gonna lie.  Friday at the Oaks was miserable.  But that experience just made us that much more grateful for the moments of sun we had at the Derby the next day.  If you find yourself with tickets to a soggy day at Churchill Downs, I hope my little list of 13 Dos and Don'ts is helpful, but if it's raining and you have the choice, just curl up on your couch and watch the whole thing on TV.