Kentucky Derby

As I mentioned yesterday, the Kentucky Derby is a two-day affair. While Friday is all about the fillies and wearing pink, Saturday is the more traditional, better known day: the run for the roses. But again, there is more to the derby than you might realize. Did you know that there is way more that happens than just the main race? Sure – the main race may be known as the most exciting two minutes in sports. But in reality, the day is filled with fourteen different horse races, each of which is prestigious in its own right. Plus, between races, there is lots more going on from people watching to betting and drinking mint juleps.

What I Wore On Saturday

Now, as for planning my outfits this year, I have to admit it was more challenging than usual. Never before had I had to work around being eight months pregnant! Not only did I have to do the usual hat and dress choosing, but this year that dress had to be able to accommodate my current shape.

As for outfit planning, sometimes the outfits start with the dress, and sometimes the look starts with the hat. My look on Friday was definitely inspired by the beautiful Sachin & Babi dress. Conversely, this unique hat drove my entire outfit on Saturday.

Milliner Heidi Lee

In fact, I first learned of milliner Heidi Lee at last year’s Kentucky Derby. I immediately fell in love with her modern, fashion-forward, unique pieces with minimal, clean lines. Now, here’s the kicker… Can you believe that she makes many of her hats (including mine) using a 3D printing technique? Indeed, she refers to this 3D printed nylon hat style as “the new aesthetic”, a blending of the virtual and physical.

So, once I had decided on the hat, I had to choose a dress and accessories. While I don’t usually favor maxi dress silhouettes for the Derby, I found this dress style certainly worked for me this year. Furthermore, I liked the way the lines of this dress and of this bag echoed the lines of the hat. (Side note: read more about these “it bags” of the season here.)

As I mentioned yesterday, we shot these photos in Houston before I left for Louisville. I wanted to ensure I had decent photos to share here. In the spirit of full disclosure, I have to admit that the look differed a bit on race day itself. First, given the atrocious weather (cold and rainy for most of the day), I layered a jacket and scarf over this. Second, I swapped the heels for sneakers most of the day. Given the weather, muddy conditions, and my pregnancy status, I figured that was fair game this year. 😉

In Closing

I hope you enjoyed the Kentucky Derby features – both the outfits and the insight into the races. Have you ever been? Would you like to go? It certainly is a bucket list activity for many – and rightfully so!

Now, come back this afternoon… We have a special treat, as Ashley shares what I think may be our first ever DIY project here on Wear + Where + Well. It’s a lovely little Mother’s Day gift idea that you’ll want to recreate for yourself!!

Photos by Maritere Rice


Details of My Look

Anthropologie abstraction maxi dress | Cult Gaia mother of pearl ark bag | Heidi Lee vortex sun hat (similar styles here and here) | Jimmy Choo strappy sandals (old, similar styles here and here) | Bauble Bar crispin drop earrings (also available here) | Jennifer Fisher bracelet (similar styles here and here) | Hermes bracelet (similar styles here and here) | Ray-Ban aviator sunglasses | NARS ‘jungle red’ lipstick | OPI ‘gelato on my mind’ nail polish


  1. Ashleigh says:

    This is such a gorgeous outfit, Carrie! I think that dress looks absolutely perfect for a derby, and that hat is seriously amazing! I love the tech-y origin, and the result is totally chic and fashion-forward!

    xx Ashleigh // Fashion in Flight

    1. Carrie says:

      I really appreciate all that, Ashleigh! Many thanks. Xo

  2. Jenn Lake says:

    Perfectly put together! LOVE!

    1. Carrie says:

      Many thanks, Jenn! This year sure brought its own unique styling challenges. 😉

  3. Jennifer says:

    Such a gorgeous dress and you styled it perfectly!

    xo, Jennifer

    1. Carrie says:

      That’s so sweet of you! Thanks, Jennifer.

  4. Sheri says:

    HI Carrie,
    I imagine this dress looked cute with sneakers 🙂
    The Derby is a bucket list item for me. Maybe one day….


    1. Carrie says:

      Hee! Thanks, Sheri. My metallic Golden Goose sneakers…

      Oh yes I hope you are able to make it happen. It is certainly a unique experience.

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