Wednesday, May 2, 2012

What Not To Wear: Kentucky Derby

So as all socialites know- this weekend is the Kentucky Derby. You know what this event means to me? Nothing. Absolutely nothing. 

But, I like any and all excuses to try something new and hang out with people during weekend DAYS rather than weekend NIGHTS. With this in mind, last year (and last minute), a group of my friends decided to join a larger group to head off to a Kentucky Derby party. Without realizing the full magnitude of what it takes to get Derby ready- I grabbed a stupid beach hat I have and a Spring dress. Ready to Derby it up, right???
{^my 2011 Derby Outfit. So bad.}


Wow- I look like Paddington Bear. And can you tell from the crowd below that I had no idea how much people would get dressed up... 
That's not to say that I still didn't have a blast with my friends:

{^Miranda and me with our hats full of secrets}

It just means that I will not be repeating my mistake for the 2012 party and looking like the love child of Paddington Bear and the killer in "I Know What You Did Last Summer"

Because really Caitlin....
 Know less how to dress for the Derby- I dare you!

2012 big hat, conservative dress purchased!

Are you going to celebrate the Derby this weekend?



| C AND C | Sarmin said...

I love the Derby hats that I see on TV. I would totally wear them if I was actually going to the Derby. Last year I got two really big beach hats, I was so excited that I was going to finally wear them in CA...Yeah totally forgot them at home.

PS: I saw a squirrel in San Diego, it made me think about you. I didn't feed it tho, took a picture.

Jamie said...

Hahaha, you make me laugh. I've never done the derby thing (much like you, just hasn't ever meant anything to me!) but living in the South, it's apparently kind of a huge deal. Seriously, if I were to go, without any frame of reference, I totally would have made your outfit look fabulous. :)

Whitney @ EHFAR said...

Hahaha... I love this post so much. I'm from Kentucky and sadly I have not been to the Derby :( Maybe one day! I have some hats that you could've borrowed :)

Diane said...

haha! this post made me laugh and get really excited for the derby party i'm attending on saturday. :)

erica said...

awesome post! haha. I am having a Derby party this weekend, and I am so excited to see all the hats that everyone is wearing. xo

erika sorocco said...

I don't think I would ever be able to attend a Kentucky Derby party - I just don't look good in hats. You, on the other hand, look adorbs! :)

Lindsey @ The Hill House said...

Oh, I would LOVE to dress up for the Derby and celebrate. I tried to talk my hubby into going last year, but we couldn't make it work. I always think of Julia Roberts in Pretty Woman at the track stomping in the divots and I just want to replicate the whole scene...Big hat, polka dot dress...The works. :)
We will be on the lake celebrating Cinco de Mayo so no Derby for me, but I can't wait to see what you come up with this year.

Slamdunk said...

Haha, we had friends who always had a big Derby bash, but we never were able to attend.

Now you have set the stage with anticipation Caitlin: looking forward to your 2012 look post.

Panty Buns said...

Oh boy, do I ever have ideas - mostly naughty
ones, of course!

You and your friends are dressed perfectly
for the Kentucky Derby days. I love the floppy
hats and all the "Southern Belle" looks. The
dresses are pretty and feminine. It wouldn't
surprise me at all if there were even more
colour at the Derby this year.

The Kentucky
Derby this year is May 4th and 5th? Friday
May 4th is
"No Pants Day" and Saturday May 5th is Cinco
de Mayo!

I have been ordered by a fellow fashionista blogger to
participate in "No Pants Day" with photos as proof
but am absolutely terrified of actually doing it
(going out and getting the
fame in panties I've always claimed to want - by actually going
out in public dressed like I am in my lingerie review videos, or
worse, getting famous by being arrested and jailed in my

I would, however (fantasy), have loved to be just below the
camera modeling "No Pants" fashion in the bottom photo in
front of you and your 7 lovely friends. I am very incorrigible.
You're daring me
to know less about how to dress for the
Kentucky Derby?
Well here's how little I know:

I'd be inclined to try to find an Indigenous Mexican designed
peasant top (Cinco de Mayo) to go with my full brief panties
on display ("No pants Day") and be holding out a few racing
riding crops for you and your friends to use as you
watch the Derby.

How's that for knowing less about how to dress for the Derby?

Angela said...

Look so fun. I love hats but there just isn't occasions to wear here in Socal.

Bonnie said...

Mr. A works security at the racetrack once a week, so we know allll about the Kentucky Derby!
Twitter: @GlamKitten88

Bravoe Runway said...

This is really awesome! I actually won't be doing anything for KY derby but I hope to attend someday! Love your dress and the hat looks great as well :)

Kim Axani said...

You can so rock a big hat - you look great! And that coat in the first photo is so fabulous.

Unknown said...

You look so cute! I had no idea people got so decked out for this! It looks like a ton of fun!

The Urban Umbrella

Tina said...

ohhh shit! i always forget the kentucky derby goes on.. mostly cos i just dont give a shit lol ive never once cared! but it looks fun! well the big hats part does... and the drinking... but thats it! lol but i like how you dress! but girl get a BIG fancy hat! lol like obnoxious! thats what i would do lol

Jax said...

Ohh, those floppy hats!!!! You already know how I feel about those. But, since it's for the Kentucky Derby I will let it slide ;) LOL You ladies really do look great!!!

Mandy @ In the Fashion Lane said...

OH MY....I am cracking up. Paddington and the IKWYDLS killer. The party sounds fun. Your friends plan the coolest events. My friends and I need to step up our game.