Sunday, April 25, 2010

How To Dress For The Kentucky Oaks and Kentucky Derby 101

OK, it's officially Derby week people!  The Kentucky Oaks and Derby take place this Friday and Saturday, respectively.  Now, I grew up in Louisville, KY (and still live here) which is where the Derby is run ... at Churchill Downs to be exact.  And, while I've never gotten into the actual horseracing scene, Oaks and Derby are, to me, like prom.  It's not about the date... it's about the dress... and drinking (but you shouldn't be drinking at prom, and I can't drink this year, so... the outfit I guess!)  Ladies (and some gentlemen) spend weeks and big bucks searching and planning out the perfect outfit and complimenting hat for the Oaks and/or Derby.   Many celebs get in on the action, too!  It's quite the social event.

Despite the rich history and tradition of wearing the 'perfect Derby hat', I really find hats annoying and try to wear them as little as possible.  That said, I ditch the hat for Oaks, but rock it for Derby.  My own special treat is to have my hair blown out for Oaks... which is way cooler to me than wearing a hat. (I'm seriously in the minority on this hat-loathing thing, but I can't help it, that's just me.)

Being prego this year has limited my clothing options, yet opened-up my shoe options (since I'll probably be rocking some coordinating flip flops for most of the day!)   Same as last year, Oaks Day is going to be a "pink-out" in support of breast cancer research (hence the super-pink outfit you will see below!)

Some Tips for Dressing for Oaks/Derby:

* Bring flip flops to wear to and from the car, then stow them in your purse during the day.  Believe me, unless you are Beyonce, you will not be able to get your car within a half-mile of the track OR be dropped off super-close... you've been warned!
* No umbrellas allowed, so pack a 99cent emergency poncho... it's spring in KY, so bring it no matter what the weather man says.
* Pack a small towel in your bag.  Most of us will be outside all day (even if not, you have to walk outside a lot just to get in and out!) and it's nice to have a rag to wipe down your chair, shoes, mop up spills, etc... this is kind of a mom thing, but totally worth the extra thought! 
* Plan an outfit that can be worn when it's 90 degrees or 50 degrees... aka, have a jacket/ cardigan option!
* If you plan to go to the infield at all (which, IMO is where all the fun is!) DO NOT wear something you'll want to wear again and rock some wedges if you want to wear heels since it's grass and could be muddy.
* READ ALL THE CHURCHILL DOWNS RULES ONLINE before you go.  There are some crazy ones regarding what you are allowed to bring into the track and what you are not... think sunscreen, sanitizer gels, etc.... it's kind of like getting on a plane.  Just read before you leave, because you will NOT want to head back to the car once you get to the gate!
*  Wearing an expensive hat?  Bring a thin plastic garbage bag in your purse to stow it in... just in case it rains.  I've seen many-a-hat get destroyed in a pop-up shower!
* Lastly, since you'll be bringing all this crap into the track with you, I wouldn't suggest going "wristlet" for the Oaks or Derby.... find a cute tote or large purse and bring what you need .... it's a long day!

So, what have I come up with this year?


Dress: J.Crew Collection
Cardigan: J.Crew Jackie in Shell
Bag: J.Crew Metallic Thompson Tote
Jewelry: Ann Taylor (yeah, I know the tag is still on the bracelet!)

Here I have a white Jackie on with a different J.Crew-Supernova-Necklace-like necklace on.  I still think I'm going to do the Jackie in Shell (since it's a pink-out) but this is another option.


Dress: A Pea in the Pod
Cardigan: J.Crew Jackie in Pink Frost
Jewelry: Ann Taylor

Here I have on an ATL cardigan in a Dark Fog color.

Again, the White cardigan is an option, but I think I'll prbably still with the Pink Frost.

Hat: Dillards

Last year I wore:

J.Crew Sateen Pencil Skirt in Seashell, J.Crew Cardigan, lots of pink pearl long necklaces
Sigh... a wasitline...

J.Crew silk dress and long grey necklace (and the same grey hat I'm wearing this year!)
{Double} Sigh... I sold this on the JCA exchange earlier this year.... not sure I would ever fit back into this in a size 0 again!

Are you heading to the Kentucky Oaks or Derby this year?  Have any great advice or want to share your cute outfit??  I'd love to hear about it!


  1. I'm not going but we are throwing a derby party as a surprise for my dad's 60th birthday! I am wearing a floral dress from H&M and hat from Kohls.

  2. I love your floral dress. It's so snazzy w/the dark grey cardigan.

  3. I am SOOO glad I found this post, I have been looking for someone who has been to the Derby before! I am going for the first time this year! I posted about my Derbt outfit here:
    For The Oaks, I am planning to wear a pink and white Diane von Furstenberg wrap dress. Probably no hat for the Oaks, but of course for the Derby. Thanks for these tips, they are very helpful!


What Are You Thinking?