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Just an overcommitted girl trying to keep up with it all. Mom of three, co-owner of Lemonade PR, sports lover and F1 enthusiast always counting down to the Kentucky Derby. 

Derby Style: Pretty in Pink Gingham for Kentucky Oaks

Mar 26, 2018

Oh hey Monday. This week is going to be a bit of a doozy with tons of projects and meetings on the calendar for work. Plus, spring break is next week and I feel like preparing for a road trip with kids is another full-time job. We’re going to, wait for it… Disney World.

Yes, despite my cold dead heart, I am a sucker for Disney World. I just love it. Love theme parks, love rides, love Mickey Mouse. I’m also really into anything that fully commits to a theme. The whole idea of being immersed in the world of Walt Disney is up my alley. Also, Reese is REALLY into Minnie Mouse so I feel like we should take her at her peak fandom. Either way, we’ll need you to send prayers because I can already see myself losing my shit on Main Street USA when I’m surrounded by slow walkers, dawdlers and people who just stop for no reason right in the middle of a crowd. Just thinking about it makes my blood boil. I’m also going to need a second mortgage for the amount of snacks my kids will want to eat. I’m a sucker for a Pineapple . Whip and a Mickey Mouse ice cream bar though.

Anyways… on to the Derby fun.

Anyone else having a hard time getting in the Derby spirit when it’s still freezing outside? I’m going to need spring to start cooperating soon so I can start to fully embrace dresses, sandals and pastel colors. This Likely dress from Dress & Dwell helps a little though. This is the perfect Oaks Day look, especially if you’re inside in one of the fancier areas of the track – think Jockey Club Suites, Turf Club, Millionaire’s Row. 

I love how this bell-sleeve jacket give it a little bit of the royals at Easter service vibe – although I in no way think I’d ever be put-together enough to attend a royal-anything. Sorry quick tangent here, but anyone else here totally obsessed with all things royal after watching The Crown? I am have an unhealthy obsession with Prince Phillip after watching season 2… we’re talking a deep-dive with documentaries, endless googling, etc. Sorry… back to the outfit.

If you have Oaks tickets, don’t forget to incorporate pink into your look. You don’t need to go all out, like I did here (shoes included). But it’s like wearing green on St. Patrick’s Day, you’ve got to wear a little bit of pink. If you don’t love sporting pink, I suggest adding it in to your fascinator or hat with some feathers or flowers.

LIKELY Keely Pink Gingham Dress 
from Dress & Dwell 
Sam Edelman Pink Heels
Dagne Dover Petite Tote
Headcandi Derby Fascinator


Quick tip on Likely dresses – SIZE UP. Possibly even two sizes up. They definitely run a little small and are form fitting. I just borrowed this dress for this shoot and it was a little snug (I’m sure you can tell). I’ve tried on a few of the ones Dress & Dwell carries (they’re also available at Revolve) and I need to go up in size on all of them. If you’ve got wider hips and it’s one of the more fitted options, I might go up two sizes. Or if you order, I’d get a couple sizes to see what works best. I’ve pulled some options later in the post so you can see some of my favorite styles. Grace from A Southern Drawl rocks them all the time (and looks fantastic), so if you want to see how they look and fit, I’d recommend checking out her site. 

And on the fascinator, you all know I love Headcandi. If you want something custom, just head over to her etsy shop and you can customize any of her pieces of have her whip something up special just for you. I’d recommend reaching out sooner if you already have a dress or color palette in mind so you’re not down to the wire.

LIKELY Derby Ready Dresses 


Photos by Tabitha Booth

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