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A Derby Day Style Guide (Ladies, Hold on to Your Hats!)
Let’s be honest, you might not have ever celebrated the Kentucky Derby. Or even seen a horse race down a track, but that shouldn’t stop you from embracing your inner Southern mad hatter socialite (come on, YOU KNOW you have one in you) and being extra bold at this Saturday’s BYT PRESENTS: PRANCIN’ (A DERBY DAY PARTY). Besides, after a few of those celebrity-bartender crafted mint juleps (or anything from the open bar-more on which tomorrow in our special BOOZE PRANCIN’ PREVIEW), you inhibitions are going out the window!
But still, getting dressed for such an esteemed occasion can be tough, which is why we reached out to four local style gurus to get their take on what you ladies should be wearing this weekend. From the bold to the brave, to everything not-so-subtle in between, hold on to your hats — this is NOT YOUR MOTHER’S DERBY STYLE STORY.
Rachel Cothran
— Corcoran Gallery Girl, Project Beltway betty and 1/5 of our favorite pop-up shop, Butler + Claypool
- LOOK #1
“A big, bold hat is a Kentucky Derby tradition, with the sartorial competition arguably a sporting event in its own right. This one was made by one of my biggest girlcrushes, Brittany Watson, a grad of the interior design program at the Corcoran College of Art + Design. Hers is a riotous, exuberant celebration of spring and a nod to the Derby’s tradition of the Garland of Roses. I built the rest of the outfit around the hat, adding a white, ruffled dress and equally playful accessories like a wicker clutch and Charlotte Olympia’s Rose heeled sandals, which beg to be paired with this hat.” (Dress – Asos, Shoes – Rose by Charlotte Olympia, Clutch – Talbots, Insane Rose Headwear – The House That Lars Built)
- LOOK #2
“This look is inspired by twenties fashion. Spring and summer is a busy time of year, so we’d all be smart to buy things that serve multiple purposes. This dress–only $158 at Yoox–works for weddings and ‘The Great Gatsby’-themed parties. The cloche fulfills the hat requirement (yes, there is a hat requirement) but remains manageable after a few Mint Juleps.” (Dress – YOOX.com, Hat – Anthropologie, Shoes – ModCloth)
- LOOK #3
“An all-over floral dress is perfect for the Derby. Both the dress and hat feel very English.” (Hat – Etsy, Dress – Stella McCartney sold by Liberty UK, Sunglasses – Fred Flare, Wedges – Anthropologie)
Holley Simmons
— Adorable Fashion and Dining editor at The Washington Post Express and FW plus BYT’s resident DIY Columnist!
- LOOK #1:
Since I could never suggest anyone wear seersucker or Lily Pulitzer in good conscience, this dress is a worthy compromise. Lightweight cotton is prettied up with bright bouquets of flowers. Add to it teardrop earrings by D.C. designer Beth Silverberg and an equestrian-themed hand mirror and you’ve got the right mix of preppy and edgy. (Dress – Anthropologie, Shoes – Rachel Zoe for Piperlime, Earrings – Jewlery by Beth Lauren, Compact – Moschitto)
- LOOK #2
You know Zelda Fitzgerald loved her a good old fashioned horse race. I image she’d wear something like this flowing floral number from the ’20s with a snug sequin hat. To keep things lady-like, throw on some lacy gloves, strands of pearls, and sparkly shoes. (Vintage Dress – Etsy, Sequined Turbin – Etsy, Lace Gloves – Etsy, Vintage Pearls – Etsy, Gold Heels – Etsy)
- LOOK #3
Derby parties are your chance to go overboard. To me, that means showing a little tummy and wearing a loud print skirt. And no Derby Day would be complete without a wide-brim hat so floppy it blocks your view. Because what else is there to look at, really, other than the julep in your hand? (Crop Top – Steven Alan, Maxi Skirt – Ralph Lauren/Etsy, Heeled Sandals – Zara, Floppy Hat – Rachel Zoe for Piperlime)
Kristin Guiter
— Head Babe In Charge at KKG Arts + Culture Communications, plus 1/5 of our favorite pop-up shop, Butler + Claypool
- LOOK #1
Inspired by the Great Gatsby-era fashions as-of-late, my Derby day style vote goes to 1920’s garden party! Ladies can do a drop waist sundress with a long necklace and complete the look with a parasol to shield from the sun. (via, dress by Louis Vuitton)
- LOOK #2
The Jardim lace dress (“jardim” means garden in Portuguese, by the way) is perfectly lady-like for the high-style yet day-time derby party. The pink ribbon on top of the lace is very vintage-inspired and designed to be seen in light so the detail can be admired. The color calls for one of my favorite MAC lip colors,Impassioned, a neutral wedge, lace-accented hat, some vintage pearls, and a beaded bag. (Jardim lace dress made by Yoana Baraschi, sold by Anthropologie.)
- LOOK #3
I’m loving the peachy tones this spring! And this flowy chiffon strappy sundress will be comfortable and elegant on a breezy afternoon. Worn with either a nude or gold sandal, it should we warmed up with gold accessories and a floral hat. (‘Rory’ High Low dress by BCBGMAZARIA)
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Morgan Hungerford West
— The Editrix and Spiritual Czar of DC lifestyle magazine/blog PandaHead and all around Arts&Crafts Cutie (remember those French Embassy teepees?!)
True story: Morgan once bought a brown, polka-dot dress for the sole reason that Julia Roberts wore one in that Derby scene in Pretty Woman, but otherwise she’s in full support of weird-ing up a Derby Day outfit (as opposed to going full-on CLASSY LADY).
- LOOK #1
This is so fun (and it gives me ALL the good Pee-wee Herman vibes) – if it’s SPRING-CHILLY it’ll look great with a leather jacket thrown on top; if it’s warm just load up on turquoise rings. Either way: light-brown leather oxfords or ankle boot, and a neutral, brimmed hat with flowers stuck in the band (think: Rolling Thunder-era Dylan). (Dusen Dusen Fruit Stand Shift from Anthropologie)
- LOOK #2
I mean, lace is Derby-appropriate, right? Muck this up/dress this down with some moccasins, Ray-Bans, and a ratty, wide-brimmed straw hat and you and I are IN BUSINESS. (Black Dahlia Maxi-Dress from Free People)
- LOOK #3
60s-sweet but still from Outer Space, this vintage treasure is insane in all the right ways. I don’t even know how I’d style this, but a black hat and some sort of avant garde-looking black bootie would probably be a good start…and WINEHOUSE EYELINER, FOR SURE. (Vintage 60’s Teal Garden Dress, from Sisters of the Black Moon)
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Many thanks to our fantastic style mavens for their input! Tickets for BYT PRESENTS: PRANCIN’ (A Derby Day Party) are still available (somehow?!). Can’t wait to see all of you in your best dressed this Saturday!
He was living the life of a single man, despite having his eye on that one brunette girl.
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and sew the ribbon down the center of the T shirt by hand or with a sewing machine.
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Thanks so much for featuring my 1920’s sequin cloche!