Q and A with Emmy-Winning TV Star Carson Kressley

Horse Racing Radar
Rich Bieglmeier
Rich Bieglmeier is a Staff writer for Horse Racing Radar
Wednesday, April 28, 2021

Along with one of the biggest horse races of the year, the Kentucky Derby is also known for its fashion. This week's The Players' Edge Guest, TV personality, Carson Kressley knows a thing or two about style and is a World-Champion Saddlebred rider.

Carson has been around horses his entire life and they are still a big part of his world today. Get to know a side of Carson away from TV's bright lights.

HRR: You grew up around horses, your grandparents owned a pony farm in Pennsylvania, what is your first memory of riding a horse (or pony)?

Carson Kressley: Some of my first memories in general revolve around horses and ponies.  I grew up about 100 feet from the barn and I was literally surrounded by a herd of ponies since birth!

HRR: You liked horses so much, you bought your own Saddlebred horse at 15, named Daddy's Money, tell us about Daddy's Money.

Carson Kressley: Yes, while I grew up around ponies and showing them, as I entered my teens, I wanted a horse.  I had seen saddlebreds competing at the same shows we took the ponies too and I was smitten.  They were big and fancy, high stepping with fabulous tails - and the riders wore suits, tops hats and bow ties!  I HAD to have a Saddlebred and I have been involved nonstop since 1985.

HRR: You competed in equine events as a child and won a world championship as a part of the 1999 US World Cup Saddle Seat equitation team, describe the experience?

Carson Kressley: Well actually I was on the World Cup team in 99 and won a team Silver for the United States in the five gaited equitation section.  I won my first Saddlebred World Championship in 2009 aboard Enchanting Memories in the amateur five gaited divisions.  Both were thrilling beyond words - a lifelong dreams realized.  I still can't believe my good fortune.

HRR: You and your sister own a farm in Pennsylvania that's home to your Saddlehorses. Tell us about your horses? 

Carson Kressley: Yes, we have farm that's been in our family for over 100 years. We raise all the typical Pennsylvania crops as well as all of our own hay and straw for bedding.  We have a variety of horses there too, mostly Saddlebred retirees (there are a couple of World Champion "lawn ornaments" enjoying the good life) and broodmares.  We typically raise between two and four foals per year.

HRR: Would you consider having a barn of thoroughbreds? Why or why not? 

Carson Kressley: I think I would have to move to Network TV for that to happen!  That would be fun, but I don't think it's in the cards!!!

HRR: Describe your first experience with horse racing?

Carson Kressley: It was a summer vacation to Saratoga when I was in my teens with my parents.  We saw the thoroughbreds run as well as harness racing at night.  I loved the town, the horses and the whole Saratoga vibe. I was hooked.

HRR: One of the things you are known for is judging, especially fashion. Which fans have more style, Kentucky Derby or Breeders' Cup and why?

Carson Kressley: Well, I'd rather not say which is better or worse... But I think there are two distinctly different styles in each event. The derby is a big party, and you'll see everything from tube tops and wildly colored golf outfits in the infield and neckties and couture millinery up in the grandstand.  I love it all.  Everyone does it their way and gets involved.  I love that.  Fashion is about having fun and derby day is great example of that. 

Breeders Cup is more of an insider event and you get more die-hard thoroughbred breeders, owners and fans.  Therefore, I think, it is a bit more restrained.  I like that it's in the fall and we can create very very different, cooler weather looks compared to the lighter brighter looks at the spring meets.

HRR: When it comes to judging horses and making your horse racing picks, how would you describe your handicapping methods? 

Carson Kressley: I'm terrible.  I go by the silks' colors, the name, and even if it looks bright and pretty headed to the post.  None of this has worked in my favor!

HRR: One final question, the winning Kentucky Derby trainer will be interviewed on TV in front of millions of fans, what fashion advice would you give them?

Carson Kressley: Having a horse in the derby is like being nominated for an Oscar. Be red carpet ready, have fun with the look, choose the color and vibe that makes you feel Supremely confident.

You can keep up with Carson at:

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