Derby Day - Among Other Things (The Blog)

Derby Day

Not that a girl needs an excuse to express her inner Southern Belle, but today is a good one.


Somehow, it’s nearly May (and 2014, when did that happen?) — more specifically, it’s T-minus 10 days ’til the 2014 Kentucky Derby.

Or if thoroughbreds aren’t your thing, let’s go this route: T-minus 10 days ’til the next weekend when it’s socially acceptable and encouraged to get dressed up and day-drink before noon.

Money, horses, hats and time-honored traditions. Oh, and the unofficial start of Seersucker Season. (Hay, boys.) Hell yes. I’m fired up just thinking about it!


While it’s always been a huge event in the world of horse racing, the Kentucky Derby has also become quite a talked-about event in the style realm.

Do you know what you’re wearing for the most exciting two minutes in sports?

If no, fear not: Jess, Mackenzie, Carly & I teamed up with vineyard vines to showcase their 2014 Derby collection — and to help you figure out what to wear on D(erby) Day.


Personally, I went with a rose-print skirt, colorful wedges (easy to stumble walk in) and — of course — a striped hat. I’m not one to shy away from a bold-and-bright ensemble and this one works because I kept it to two colors.

Here’s some advice on what to wear to a Kentucky Derby party or event:

  • YOUR HAT: The bigger the better, ladies. I like one with a wide brim.
  • YOUR OUTFIT: When you think Derby, think below the Mason-Dixon line. Anything goes — as Carly proves in her cobalt pants — but whether you’re uber-femme or no-frills, keep the silhouette simple.
  • YOUR ACCESSORIES: Your hat is the crowning jewel on Derby Day, so there’s no need for statement jewelry. Though a cute pair of crystal-drop earrings never hurt.
  • YOUR BAG: Derby veterans actually carry two bags on the day-of. Inside a larger carry-all, they keep sleek clutches for placing bets and mingling on the sly.

If your guy is party-going with you, advise him to wear seersucker, prints and pants in spring-like shades of red, orange and emerald — all perfectly fitting for the occasion. vineyard vines is the official tie maker of the Kentucky Derby, so pull together his look with a sleek neck- or bow-tie. I’m partial to the patchwork pattern.


As for the women’s collection, this season’s selection is lady-like meets laid-back casual. I love how Mackenzie kept her look classic in a pastel dress and metallic flats.

Carly’s horsebit blouse conveys the fun, whimsical tradition people associate with the Kentucky Derby lifestyle. And of course, there’s a lot of stressful creativity related to finding the perfect hat (which comes first — the dress or the hat?), and I love how Jess mixed mint and navy, lightly layering with a jean jacket for a traditional touch.


Now, if you’re heading to your own backyard rather than Churchill Downs (or in New York — to a rooftop or questionable sidewalk situation of sorts) here’s some tips for hosting a themed Kentucky Derby party:

  • THE DECOR: Pick up red and white roses for your floral arrangements (a blanket of red roses is placed on the neck of the Derby winner).
  • THE FOOD: Serve finger foods to start (like these Instagram-worthy sandwiches), then up the ante with a Southern barbecue spread of classic pulled pork sandwiches, roasted corn and slaw-based salads. Traditional Texas brisket or pork roast with a tasty bourbon glaze do well as main course options, too. If you’re coming to my party, know that we’ll be ordering in. #domesticgoddess
  • THE VIBE: I’m more of an Infield kinda girl, myself — which is where you’d head if you’re more interested in a party (and seersucker-suited party-goers, hel-lo!) than the actual race. You with me? Otherwise, bust out your fine china for a spread worthy of Millionaire’s Row, which is the expensive box seats at the race.
  • THE DRANKS: Bellinis and Bloodies make for an easy-to-ensemble beverage bar, but of course, you must have mint juleps. Woodford Reserve has a great recipe.


*I’m wearingSleeveless TopRose Print Skirt & Race Day Bow Hat c/o Vineyard Vines, Pour la Victoire wedges

Click to view/shop: Jessica’s outfit | Mackenzie’s outfit | Carly’s outfit |
Shop vineyard vines’s 2014 Derby Collection (order for guaranteed shipping before 5/25/14)

Rebecca Dale Photography | #vvderby14


Join the Convo:

Back to Top


Select your subscription: