The Not So Darlin 2022 Derby Style Edit

So, here's an honest admission: My love for the Kentucky Derby really isn't about racing at all, it’s about the fashion! Since I was a kid, I've been mesmerized by the big hats, bright colors and what the celebs wear on the first Saturday in May.

As a Louisvillian growing up not far from Churchill Downs, I’ve been lucky enough to experience the magic of both the Derby and the Oaks, plus all the fab festivities that go along with both. But nothing about this yearly spectacle has made my heart race as it did 13 years ago at the 2009 Oaks. Little did I know I'd be resurrecting my senior yearbook "Best Dressed" superlative from Fairdale High School class of '97!

Here's the story: In '09 Bravo TV debuted Ladies First: Bravo at the Kentucky Derby, co-hosted by Access Hollywood's Nancy O'Dell and the Real Housewives' Bethany Frankel, which gave viewers an inside look at the history of the Oaks fashion and its festivities, the highlight being a live fashion show on Bravo. I'm a pretty creative gal and for several years I had been making my own hats with 2009 being no exception. My dress was a very affordable and very cute little frock which I szchoozed up to be runway ready for the Oaks live fashion show. So there I was, confidently and proudly walking that pink carpet in an inexpensive but totally stylin' ensemble topped off with a hat made by moi!

I was beyond thrilled to make it to the top five and I vividly remember judge Bethany raving over my outfit and how it gave her all those 'NYC vibes'. Certain that the title would be mine, Miss Thang Bethany changed her mind at the last minute and went with the southern belle style worn by another finalist (yawn!). Lesson learned? Always be true to your own style DNA and forget about anything that remotely looks like Scarlett O'Hara from the 1800s 😂.

Now, let's talk about 2022:

For both the Oaks and the Derby, hats are a MUST and when choosing your outfit keep your headpiece in mind because not only does it have to be a statement maker, you're going to be wearing it all day so it should also be comfortable. Additionally, keeping the overall look to a simple palette as I did here - in this case, head to toe creams and white - makes for a super chic, striking silhouette. Outfit and hat from Louisville's The Urban Market.

You can go all-out, A+ classy or be a bit more casual, because pretty much anything goes in Kentucky on the first Friday and Saturday in May! My choice more often than not leans toward the dressy side as with this beautiful, tonal look above from Prospect-based Pink Julep Boutique. However, I encourage my NSD crew to stay true to yourselves and your own style DNA and go as dressy or casual as you you!

This bold, floral turquoise look and matching hat from Pink Julep Boutique is guaranteed to be an instant head-turner on Oaks Day, Derby Day, or any day you feel like dressing up with an extra dose of oomph! Remember with daring, dramatic colors like these to keep your accessories simple, with fresh, natural makeup and easy breezy hair.

Finally, the most important advice I can give you when planning your 2022 outfits is to remember the Not So Darlin 4 F's: fashion, function, feet and freeze, or you’ll end up using my favorite f-word 😉 My hubby says I always choose fashion over function, which has been true in the past, but I learned the hard, cold (literally) way, so follow these two top tips and you'll be good to go, I promise!

  • DO NOT end up like me in the past with 'grocery feet' (gross!) and an empty pocketbook doing a barefoot walk of shame after Race 12 at Churchill Downs on Oaks or Derby Day because your heels have gotten the best of you; flip flops (fashionable ones, of course) in your bag are a must.

  • You also don't want to freeze your butt off all day so make sure to follow the weather closely leading up to the big days. Cue my Forrest Gump voice: "Life’s like Kentucky weather, you never know what you’re going to get".

And last but not least, be sure to follow all my Oaks and Derby style updates on Instagram now through the first weekend in May at

Happy Oaks and Derby 148!


Opening Photo Dress & Fascinator: The Urban Market

Photography: Tina Takes Photos

Makeup: All Glowed Up by Erica

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