Talk Derby to Me…Derby Fashion do’s and dont’s. Part I

Around here, the spring rain, the wild temperature fluctuations, and the hunt for the perfect outfit all mean one thing:

Its Derbytime in Louisville.

KY Oaks
CT @ KY Oaks, photo by Dan Dry

As we countdown for the Thundering hooves at the 138 Kentucky Derby, lets highlight this week a few tips and tricks for surviving the track!

The Derby is a time-honored tradition of Southern Style and Grace, highlighting 2 of Kentucky’s most precious assets:

Beautiful women and fast Horses.

Don’t ignore the pomp and circumstance that is the Derby. And Don’t become a fashion victim. Whether you shop at JC Penney or Rodes, good fashion is about common sense, and your style.

Over the next few days- watch the blog for tips you can use, or share with your out of town derby guests.

This will be my 20th Kentucky Derby, so I will share a few things I have learned along the way…


Celebrity Luncheon

Fashion for the Ladies:

**According to stylist Andre Wilson, of Style Icon, the hot color this year is coral.

  • Always buy a coordinating jacket, sweater, wrap with your outfit. Be safe, not sorry. I have seen it sleet (1989) or be 85 degrees, its Kentucky, so you never know!
  • Fabrics: Silk can wilt or melt in the humidity, so be weary.

I had a $350 silk Robert Rodriguez dress melt under cover of the 3rd floor. It grew 2 sizes, and the silk rose on the front “died”.  Cottons, linens or even flowy synthetics work best in inclement weather.

Gals on the 3rd floor
Derby fashions from years past ( my hat came from 4th street- and embellishments added)


  • Hats: Wear them STRAIGHT across your forehead. NO bangs or hair should show in the front, that’s too Ellie May. Hair tucked behind your ears, smaller hats if you have short hair.
  • Use a headband to conquer hat-hair. IT works! Or tease it up and pin half up under the hat- if you take the hat off- you can get away with it.
  • Headbands can also help if your hat is too large and slips about. Try one with a little padding to keep that chapeau in place
  • Wedges fare better than stilettos on the bricks or anywhere for 8 hour days. . Period. You can buy ½ size larger and add a foot pad under the ball of the foot, or even a full foot insole. Watch your salt and hydrate in the days before to keep swelling down.


Some of my favorite haunts for Derby Attire:

Cache’ – good for your out of town shoppers

Rodeo Drive- Local

Nitty Gritty for Vintage, fun fashion

Clodhoppers for Milly, and classic chic styles

Glasscock and Chic Boutique


The Hat Shoppe @ the Crowne Plaza is run by my friend Wayne Esterle, he is amazing. Take your outfit, and have the ladies help you.

The 4th street “wig-hat” shoppes are full of cool, fun hats that are minimal in price, and can be added to match outfits etc. I needed a silver straw- one year and found it here, then paid to have feathers etc added to it. ( see above photo- literally the only hat in town that would work!)

In Westport Village, visit my friends @ “Hataritaville” They are hand made and fun. Look for them by the Comfy Cow


This poor lady is suffering under the weight:

Wow, that looks heavy....Don't let the hat wear you.


Fascinators: I have mixed (mostly negative) feelings here. I had two friends who brought back very cool fascinators from Paris in say 2005. They were great ( looking for that pic). Now we have the “disastinators” in which they are over the top.
I like to think we can leave it to the British to be the wacky fashionistas in the group..I found a site with the biggest headpieces I have ever seen, with names like “Banana Split” and “Schnitzel with Noodles”, even the “Bull Mastiff”. Would you wear something with that name ion your head? Not me.

I digress, it might be show stopping, but “beautiful”? Some are, some are not.

Carmen Miranda?
Did she wear it? or did it wear her?

They have been mentioned in the press, due to Queen Elizabeth pronouncing new standards of dress required for entry to the Royal Enclosure at Royal Ascot.[1] In 2012 Royal Ascot announced that women will have to wear hats, not fascinators, as part of a tightening of the dress code in Royal Ascot’s Royal Enclosure this summer. In previous years female racegoers were simply advised that “many ladies wear hats.”

uhm, hon?

Follow these rules please to avoid being a fashion Don’t!
-Too big, is too big. If its Larger than your head, too large.
-Go sculptural and classy
-Fascinators are highlight head pieces, not to be confused with hats. If your headband is as big as a hat, just buy a hat.

I once saw a fascinator on a local newswoman that looked like the flock of birds that brought down Sully’s plane in the Hudson River. Don’t be that girl.

"The Banded Mongoose"


Peacock, anyone?

From Wikipedia:

A fascinator is a headpiece, a style of millinery. The word originally referred to a fine, lacy head covering akin to a shawl and made from wool or lace, but mostly feathers. In the modern usage, it refers to a woman’s alternative to hat for formal attire; it is usually a large hair decoration on a band or clip with elaborate trimmings and decoration like a formal hat and it can incorporate a base to make it a miniature hat.

Today, a fascinator may be worn instead of a hat on occasions where hats were traditionally worn—such as weddings—or as an evening accessory, when it may be called a cocktail hat. It is generally worn with fairly formal attire.Bigger than a barrette, modern fascinators are commonly made with feathers, flowers or beads The fun, fanciful ornament is often embellished with crystals, beads, or loops of ribbon, and attaches via a comb or headband; some have a small, stiff, flat base that can be secured with bobby pins. They are particularly popular at premium Horse-racing events, such as the Grand National, Kentucky Derby and the Melbourne Cup.

Hats: Same rules apply. If you want to look back at your photos 10 years from now, think about the Big Hair days of the 80’s. No one is proud of those hairstyles. Don’t do that to yourself.

Good hats & appropriate head pieces are a fashion “DO”

Cute Girls @ the Races
Cutness @ the Races

From the Churchill Downs website:

Derby Hats Heads of Distinction

What sets the Kentucky Derby and Kentucky Oaks apart from other sports and entertainment events? Is it the world-class Horses? The Hollywood stars? The romantic Twin Spires? Well, first and foremost, it’s the hats!!

Large or small, contemporary or old-fashioned, big brimmed, feathered, flowery, furry or just plain fascinating…women (and men) top off their Oaks and Derby duds with a variety of ostentatious head wear.

Part Southern tradition, part spectacle, the Kentucky Derby hat parade is much of what makes “The Greatest Two Minutes in Sports” one of the greatest people-watching events in the world! From the fantastic to the sublime, there are no rules or limits when it comes to choosing your Derby hat.

Whether to make a statement or just keep the sun at bay, Kentucky Derby hats are part of the tradition and the pageantry that make a trip to the Derby an unforgettable experience. Check out some of our favorites from prior years!

Most important to remember, be beautiful, dress well, and enjoy!


~ Cyndy Tandy

Derby 2011