Monday, April 22, 2019

Day-at-the-Races Fashion

Throughout the year there are significant Fashion Trend Monitoring Moments. First, of course, is New York’s Fashion Week, which premieres all the Couture You Will Never Own and projects the trends that you will be buying.  Everyone eagerly anticpates the Academy Awards because it is Haute Evening Gown Premiere Night. And I just learned that the NBA All-Star Weekend is also the Sneaker Fashion Premiere Week.

Kentucky Derby Museum pays tribute to it's long-standing fashion history in their Derby Decades exhibit

Kentucky Derby Museum pays tribute to it's long-standing fashion history in their Derby Decades exhibit

The Kentucky Derby is actually the Summer Track-Season-Fashion Launch Party. If you want to know what the Southern Belles, Upper Crust Connecticut Country Clubbers and Long-Island Snooty Socialites will be wearing to the Hamptons, et al, this summer, just tune in to the Kentucky Derby Red Carpet.

Yes, there is a red carpet outside an event that is centered around a horse poop covered dirt track. Go figure.

Race Day Fashion  has become such an integral part of the Kentucky Derby, that they have dedicated an actual museum exhibit to showcase it’s long history.

I remember the first time I was invited to go to the races up in Saratoga, New York. Talk about a fashion 911 crisis! I had no idea what I should wear. Thinking about it now, I have to laugh because becoming “Day-at-the-Races-Chic” is really simple.

First, it’s all about the hat! Don’t waste time and money on your outfit until you find your perfect headpiece. Everything you wear should be made to showcase your hat, not distract from it!

Second, it’s all about the attitude because Track Fashion (not to be confused with NASCAR Track Fashion….) is all classic elegance.pretty-woman-doll

Think….Audrey Hepburn.

Think….Charlotte York in S&TC.

Think….the polo match in Pretty Woman.

Think….Southern Belle meets Upper-Crust Connecticut Country Clubbing Socialite

Think….Kentucky Derby Barbie



Think….Playboy Bunny & the Girls Next Door?

No, I’m not just making sure you were paying attention! Even the Girls know how to be elegant and chic for the Derby:



Track Fashion is:

Chic, classic looks that still look fun, modern and flirty!

I have always been a fan of the classic and timeless looks. They always seem to flatter every body shape and their simplicity means you get to wild on fabulous shoes, purses, jewelry and…..hats! Here are some tips and must haves to complete the Timeless Beauty Looks. I’ve also added photos of some really fabulous classic yet chic looks. Click on any photo to get buying info!

  • Sheaths: especially with a cinched and belted waist.
  • Wrap Dresses. I swear, there is NOTHING more flattering than a wrap dress. They look great on just about anyone and they always seem the flaunt the good while hiding the bad–even if you gain or lose 50 pounds, somehow the miracle dress will still fit!
  • Strapless dresses with a-line skirts: another form flattering shape. Pair it with an coordinating cardigan and you are oh-so-preppy-chic!
  • Ankle/calf-length dresses: Sure above the knee has the in your face sex appeal, but a longer dress with a slit that plays peek-a-boo with your legs…that’s subtle-hot!
  • Pretty in Pink: and all other pastels!  Country Club Colors like pale yellow and pink or baby blue and cream are definitely high-society must-haves.
  • Floral: The Ultimate Spring-Summer Must Have –whether it’s the pattern on your dress or the flowers in your hair and on your shoes!








Classic Black, White and Oh, so Chic

Ever notice that you don’t see a lot of polka-dots until summer? Maybe it’s because of that “Yellow Polka-Dot Bikini” song? Summer always seems to catapult polka-dots back into the spotlight, especially black and white dots. I think there is nothing classier than a crisp white and black outfit– sometimes with a pop of color or without.




And there you go! Pretty simple! Stick to the classics in your outfit, and get a really over-fabulous hat and you are ready for the Summer Track Season and the parties!

About the author: Jennifer Taglione is the owner of this fabulous website Stiletto Sports. Despite writing well over 500 posts, she still maintains that she is not a sports writer! She is however a huge fan of Kurt Warner, Larry Fitzgerald, Mark Sanchez, the Celtics, and totally kicks butt on March Madness brackets! Connect with her by following her on Twitter @StilettoSportsJ and subscribing to her weekly newsletter. For more info check out the About the Editor page!

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6 Responses

  1. Jan Crowe Said,

    I am a contestant in the Ms. Arkansas Red Hat Society Pageant on April 17, 2010. I found this Website to be the most informative site I have check out in search of what to wear to the KY Derby. I found information I will use in my Bio of my attire as a “lady attending the KY Derby in the 1940’s or 1950’s. Thank you!

    Posted on March 9th, 2010 at 12:03 pm

  2. Stiletto Jen Said,

    aw I’m glad!! Good luck to you!!!!! Stop back and let me know what happens! I’m a huge Red Hat Society fan. My mom & her best friend used to tell me about the “When I grow old, I shall wear Purple” poem and I always thought their friendship and the poem were so amazing and special. I was just thinking that I might get my friend the poem for her b’day this year because I hope her and I grow up with that same kind of bond!
    anyway, sorry about all that babble! Good luck!

    Posted on March 10th, 2010 at 11:33 am

  3. Scott@Kentucky Sports Online Said,

    I’ve been to the Derby multiple times and I will agree that your description is spot on. I did go to the infield once and I will say there is a hodge podge of outfits there.

    Posted on January 17th, 2011 at 6:22 pm

  4. tina brown Said,

    Question, going to a Kentucky Derby party. Derby attire is of course required. Found a fabulous hat. Black with hot pink trim and different color feathers. Ok to wear a plain black sun dress?

    Posted on April 19th, 2012 at 11:14 am

  5. Nate Said,

    Hi Jen. Great article.
    Where did you find the dresses you highlight?
    Specifically, where can I get the yellow dress with the pink belt and hand bag? Do you know who makes that outfit?

    Posted on April 20th, 2012 at 10:53 pm

  6. Stiletto Jen Said,

    IT’s all about the hat!
    I find that wearing a busy dress takes away from the hat. Or vice versa–everyone fawns over the hat and forgets the dress you spent so much time picking out.
    As long as you have a total look, you should be good!

    Posted on May 3rd, 2012 at 12:40 pm

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