Derby Dress of the Day: Happy {Kentucky} Derby Day!

It’s finally here – Derby Day!

Since I am the queen of countdowns, I’ll be starting my countdown to Derby 141 tomorrow morning (I’m already planning on going all out – like ALL OUT). But for now, I’ll settle in for a day of being insanely jealous watching from the sidelines. I know anyone heading to the track is already in full on Derby day preparations but I couldn’t help but pop in for one last Derby Dress of the Day to close out the season.

Yesterday, we hit up the Oaks and I can say that I have now successfully conquered a day at the track while 9 months pregnant.

Definitely got my fair share of side eyes and looks (and probably a lot of “bless her hearts.” trust me, it’s not a good thing) but it was a lot of fun. I’m glad I got to get out there even if my feet are hating me right now.

It’s been so much fun working on these posts and I hope you’ve enjoyed them (or least that they’ve helped you figure out your race day attire). I’m already brainstorming ways to improve/revamp/expand things for next year – so if you have any suggestions or ideas – send ‘em over!

I saw a ton of girls looking b-e-a-utiful at the track yesterday and today will, i’m sure, be even better. If you’re heading out there – send me a pic of your look to or tag me on instagram (@louwhatwear). Can’t wait to put together the wrap-up!

Derby 140 * Louisville, KY * Derby Dresses * Hats (4)Derby 140 * Louisville, KY * Derby Dresses * Hats (6)Derby 140 * Louisville, KY * Derby Dresses * Hats (7)Derby 140 * Louisville, KY * Derby Dresses * Hats (1)Derby 140 * Louisville, KY * Derby Dresses * Hats (5)Derby 140 * Louisville, KY * Derby Dresses * Hats (3)Derby 140 * Louisville, KY * Derby Dresses * Hats (8)Derby 140 * Louisville, KY * Derby Dresses * Hats (2)Derby 140 * Louisville, KY * Derby Dresses * Hats (9)On Kristen –
Shoshanna ‘Mia’ Dress (other sizes available here) – Available at Blink
Hat: Headcandi | Bracelets: Bourbon & Boweties  |Mint Stud Clutch: Sole Society

On Kristen –
The Navy Sweetheart from Dress & Dwell | Hat: Headcandi
Necklace:  Lulubelles from Dress & Dwell

Modeled by Kristen Cripe & Kristin Esham
Images by Whitney Neal

 Big thanks to Dress & Dwell, Blink, Clodhoppers, Dandelion and especially, Britni from Headcandi for letting us play dress up in all your wonderful Derby attire. And an even bigger thanks to a great group of gals who helped model all the looks. Lynsey, Kristen, Megan, Kristin, Ann, Hayley, Caitlin and Ashley- I owe you big time! As always, Whitney Neal captured it all beautifully and happily dealt with my madness.


Derby Dress of the Day: Shimmery Shoshanna

Last year, I wore this same Shoshanna dress in a different color/fabric combo and I can attest that it is super flattering, incredibly comfortable and with this shimmery subtle fabric – you can wear it just about anywhere.

Since the dress was so subtle, Caitlin paired it with some bolder accessories to add a little color. I also love the idea of doing a big, bold hat with this dress. If you’re still looking for something to wear head over to Blink on Lexington Road and try on a few Shoshanna beauties. The gals there are incredibly helpful and will usually pull something you’d never pick out yourself but end up falling in love with. That’s what happened when I ended up leaving with this dress last year.

Whatever you end up wearing, I want to see it! Send me a pic of your Derby or Oaks look to or tag me on instagram (@louwhatwear) and you could see yourself in the Derby wrap up next week!

Dress: Shoshanna ‘Svetlana’ Dress available at Blink Boutique ; Hat: Headcandi; Necklace: Lulubelles; Gold Clutch: DandelionModeled by Caitlin Brey.
Images by Whitney Neal.

More Shoshanna Favorites:

Derby Dress of the Day: Feathered

May Day.

It’s here. Usually May 1st is a combination of excitement for my best pal Kelly’s birthday (happy happy birthday friend!) and Derby. This year, I’m just as excited about Kelly’s birthday with a little less excitement for Derby because I know some seriously epic FOMO is about to set in. I can’t lie though, I’m pretty pumped to have FINALLY made it to my last month of being pregnant. Only 21 more days (max!). Seriously, I’m ready for this to be over and to meet that little lady (feel free to make an appearance early).

So today is what Churchill Downs is now calling Thurby. It’s what people around here call crunch time. Last minute prep is underway everywhere – spray tans, picking up dresses from the tailors, making last minute hat adjustments, nail appointments, party prep – it’s an all-out rush to the finish for everyone (even if you’re rushing to get out of town).

Over here, I’m rushing to share some of these last Derby outfits with you all. I’ve still got a handful left so I’m going to pop in twice today to share some more inspiration although I’m guessing most of you are ready for the races by now.

Today’s look, on Megan, one that is perfect for those last-minute shoppers. You probably have a great LBD already hanging up in your closet. So if you’re in need of a last minute look – grab it and then head out to pick out a colorful headpiece. You can match just about anything and you’ll be set in no time.

Little Black Dress: Leona “Emmy” Dress; Necklace: Dandelion; Feathered Headpiece: Headcandi

Modeled by Megan Kute.
Images by Whitney Neal.


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