Derby Style: Oaks Ready Rain or Shine

I’m going to start today’s post out addressing the Derby elephant in the room – the forecast. Right now, things aren’t looking ideal BUT do not let that get your Derby spirits down. My most memorable Oaks and Derby days were also some of the rainiest.

The very first time I went to the Derby, I was a sophomore in college and went with a big group of friends. Things started out a little overcast but nothing to dampen our plans of crushing the infield. Everything was just as ridiculous as you’d imagine it until no joke, a monsoon moved in. A severe thunderstorm (we didn’t know that until after the fact) moved in and dumped a ton of rain, along with wind and lightning. Our crappy, not-smart-at-all phones didn’t work so no one could warn us of the weather, we were out on an island (although one that was still infinitely better than what the one Fyre Festival was on). With nowhere to go, we huddled up and rode out the storm under the flimsiest tents known to man. Afterward, there was water up way higher than our ankles and giant mud pits everywhere. And you know what? It was crazy fun. People definitely made lemonade out of lemons, albeit very muddy lemonade. If a Derby in that kind of weather can instill a love that keeps you coming back EVERY year, then you know you can have fun no matter what Mother Nature throws your way.

Another time, Drew and I went to the Paddock with a big group of friends on a rainy day. We spent most of the day drinking Budweisers and hiding out from the intermittent storms. Then, right before Derby, a random work contact texted me and invited us up to the 5th floor for the big race. We ended up singing ‘My Old Kentucky Home’ and watching the Fastest Two Minutes in Sports from one of the fanciest areas of the track. Drew spent most of our time up there stalking Michael Jordan, who was in the dining room next door. It was absurd and we definitely didn’t belong up there (see the above-referenced Budweisers) but it was certainly something we’ll never forget. And those are just two of the maybe five or six rainy days we’ve been out there.

All that’s to say that a little rain didn’t stop our Derby parade and you never know who you’ll meet or where you’ll end up. So pack a poncho, wear comfortable shoes and don’t sweat a little rain.

Cupcakes & Cashmere Stripe Shift from Dress & Dwell
Headcandi Fascinator
Frye Sandals c/o | Dagne Dover Stripe Clutch c/o

On to the outfit, how cute is this pink stripe shift? If you scored a last minute invite to Oaks, they still have this number at Dress & Dwell. I’m not heading to the track Friday but love this for wedding season. Would be great for a rehearsal dinner or bridal luncheon too especially since it’s under $125.

I topped it off with this lilac Headcandi piece that is still available and looks way better on than just sitting on the shelf. I think with a lot of fascinators, you really have to see them on to really get a feel for the look. Hoping one of you snags this one for this weekend’s festivities.

Photos by Tabitha Booth

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mom of three, small business owner. balancing life and style in louisville, ky

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  1. Allison Petro wrote:

    Hi there, I’m a bit nervous about the weather this weekend! I am going to Oaks and Derby, first time to the races!, and I definitely planned my outfits around a spring day. Last I looked it was supposed to be sunny and 70. Now it’s rainy and 50-60! I’m a bit nervous about being cold. I had planned to bring a cardigan but that won’t be helpful when weather is in the 40s and 50s. Should I wear a coat too? I had also planned to bring flip flops for backup shoes but that sounds silly now. I’m guessing flats would be better? We are sitting in the Starting Gate Lounge covered area so hopefully will be protected from rain! Any advice is appreciated when it comes to dressing in this weather!

    Posted 5.3.17 Reply
    • Danielle wrote:

      Hi Allison! Don’t be nervous. Yes, the weather is going to be less than ideal but you will still have a blast. I would definitely wear a coat or jacket. And as far as shoes, if you want to wear rain boots – that might be your best bet for getting in and out of those suites since you may have to go through the infield. Just grab a mint julep and enjoy!

      Posted 5.3.17 Reply
      • Allison wrote:

        Thank you!!! Despite the weather, we are so excited for this bucket list event!!

        Posted 5.3.17 Reply
  2. YES! Thank you for sharing those stories because I needed to hear them. It’s going to be my boyfriend’s first Derby and I was worried that the weather was going to ruin it for him, but it’s all about what you make of it!

    Posted 5.3.17 Reply
    • Danielle wrote:

      OMG I love when it’s people’s first time to Derby!
      I could easily tell three or four more stories about hilarious and fun Derbys in the rain. It won’t dampen the fun at all as long as you go in with the plan to have a great time.

      Posted 5.3.17 Reply
  3. Christine Johnsen wrote:

    I’m going to the Derby this year for the first time and unfortunately we will not be in a suite. I have been planning on this for months and even had 2 fabulous hats made for the Oaks and the Derby but now I’m afraid to even bring them! I bought summer dresses to wear for both Friday and Saturday but now with weather forecast I’m scrambling. To figure out what to wear! I plan of brining my rain boots and a rain coat but do I wear pants? Is that even acceptable?! I’m such a fashion lover and to be honest I’m so upset over this entire thing. I need some guidence as far as fashion is concerned!

    Posted 5.3.17 Reply
    • Danielle wrote:

      Christine –
      It’s not supposed to rain the entire day. WEAR YOUR HAT! When else are you going to be able to wear them? You’ll be happy you did!
      I know Oaks is supposed to be pretty rough but I don’t think it’s supposed to rain the entire day Derby. Don’t be upset – you’ll still have fun and DON’T WEAR PANTS!!! Wear your dress and throw a jacket on over it.
      You’ll probably end up in the paddock area under cover a bunch so don’t sweat it.
      Have fun!!! A little rain never ruined DERBY!

      Posted 5.4.17 Reply
      • Christine Johnsen wrote:

        Thank you SO much for responding in a timely manner! You made me feel so much better about this whole rain situation. I also found out that we do have passes to go inside and upstairs so that is great news. If I bump into you today I’m going to have to be a fan girl and get a picture with you!

        Posted 5.5.17 Reply
        • Danielle wrote:

          Of course! So happy you had a great time – I wish I had seen you at the track!!!
          Hope you make the trip back next year! xo

          Posted 5.7.17 Reply
  4. Laura wrote:

    My friends just arrived to town from Portland, OR last night for their first Derby weekend. Unfortunately, their hats didn’t. Long story but what are the best last minute options to score a hat?

    Posted 5.4.17 Reply
    • Danielle wrote:

      Oh no! The good news is you’re in Derby country!
      A lot of the local hotels have pop-ups. My girl Britni from Headcandi has a set up at the Louisville Marriott Downtown.
      You can also check out the local boutiques – Dress & Dwell, Clodhoppers, Modern Elegance, Circe, Rhodes. Or just hit up Macy’s or Von Maur. They all still have lots of options!

      Posted 5.4.17 Reply
  5. Maria wrote:

    This post is a lifesaver! Would you recommend wearing Hunter rain boots this year for the Derby? We are in the Infield, its our first Derby, and we don’t want to look like complete fools.
    Thanks so much!

    Posted 5.4.17 Reply
    • Danielle wrote:

      Hi Maria!
      I would 100% wear rain boots to the infield. I wouldn’t wear a hat if you’re going to be in the infield either. It’s always kind of a crazy out there, rain or shine. But yeah, wear duck boots, pack a rain jacket and have the BEST time!

      Posted 5.5.17 Reply
  6. Ashley wrote:

    This is my first Derby and I was so excited to wear my cute hat and spring dress. We bought tickets for the infield and now with the rain forecast on Saturday I have no idea what to wear for shoes! I hear it can be a complete mud pit. I still really want to wear a dress, any suggestions on footwear?! Help!

    Posted 5.4.17 Reply
    • Danielle wrote:

      Hi Ashley –
      If you’re going to be in the infield – rain or shine – I recommend wearing something you wouldn’t mind ruining. I would wear rain boots for sure. The infield is always kind of a mess – a super fun mess but a mess none the less. You’ll definitely want to wear rain boots, duck boots or shoes you don’t mind ruining.
      Have fun!

      Posted 5.5.17 Reply
      • Ashley wrote:

        Is it okay to wear hunter boots with a dress?? Or will that just be silly? Thank you so much for your advice!

        Posted 5.5.17 Reply
        • Danielle wrote:

          No it’s not silly at all! I may end up going that route myself! Have the best time!!!

          Posted 5.5.17 Reply
  7. Pam wrote:

    We are not on the infield this year but in an uncovered seating area. Would it be appropriate to wear my rain boots with a dress and hat for the KY Oaks or should I wear sandals even if it rains?

    Posted 5.1.18 Reply
    • Danielle wrote:

      Hi Pam!
      I definitely think you could wear rain boots with your dress if you are in an outdoor box. I know a lot of people that did this last year for both Oaks and Thurby. My only tip would be to also pack a pair of sandals because it can go from rainy to HOT and SUNNY quick. We all know how sweaty and hot rain boots can be when that happens. So if you can pack a pair of simple sandals – I would for sure!

      Have so much fun!

      Posted 5.1.18 Reply
  8. Pam wrote:

    Its rain boots for me Friday with some cute sandals when it hopefully stops raining. I’m praying I can at least wear some cute sandals for Derby Day!!! Have fun everyone and best of luck!!

    Thanks for the advice Danielle!!

    Posted 5.1.18 Reply
  9. Mary Bet wrote:

    It’s my 1st Derby, and I’m almost reduced to wearing DEPENDS, I’m SOO
    We’re in The Aristides Lounge, but we have seats RIGHT ON THE RAIL…
    ROW A!!!
    I want to be right on that rail for all Oaks & Derby races.
    Like all these other ladies, I packed dresses, sandals and of course I wear my hats!
    We’ve been driving from North Carolina since this a.m.
    Do you recommend I stop somewhere and try to buy Rain boots?
    Thank you!!
    Your posts are so helpful!!!

    Posted 5.2.19 Reply