I grew up in upstate New York, right down the highway from the horse racing town of Saratoga. For me, there has always been such an elite aura about the horse racing society. 
Every summer, Track Socialite, Ms. Marylou Whitney and her impeccable fashion would grace the covers of all the local newspapers. It seemed every week in August she would be dressed in a stunning outfit with brand new fabulous hat!
And as a little girl I thought she was coolest lady in the world because she had so many hats! Apparently this has scarred me for life because to this day, I have a very serious hat affliction addiction obsession.
You know how when the seasons change, people switch over their summer and winter clothes? Well, I live in Florida, I don’t have to do that. But I do have to switch over my summer and winter hat collections. Yes, plural. That’s how many hats I own. It’s scary.
So I absolutely adore the Kentucky Derby because it is pretty much the Hat Party of The Year and it’s the official kick off for the Summer Track-Fashion Season.
The most important element in Track Fashion is not the perfect dress or fabulous shoes; it’s the flamboyant, over-the-top Hat. Keep the outfit basic and simple and rock the biggest, baddest, loudest, frilliest, feather-covered, rhinestone-studded, giant-bow-covering hat that you can find!
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I went online to find a few examples of fun hats. Really, it was only going to be like three hats.
Only you should never, ever, ever, send a Hat Addict onto Amazon to look for Race Track Worthy Hats. HOURS later…I had looked at thousands (literally) of hats and was only able to pry myself away when my eyes started to burn so badly that I couldn’t see the hats anymore. So….there are a lot of hats for you to look at! But if you are like me, you won’t mind at all!
The hats are broken down into:
- Classic & Timeless
- Black White & Oh So Chic
- Head Turning Colors
- Haughty Haute Couture
I tried to give descripts for all but I may have missed some! You can click on any picture to get all the buying info. They are all located on Amazon.com, because that seemed to be the biggest hat database I could find! Huge love to Luxury Divas and E4Hats because their products were really amazing!
For outfit ideas, check out my What to Wear to the Kentucky Derby piece.
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Classic & Timeless
Crushable Toyo Straw Hat
J’adore this pink and white classic hat. It’s effortless simplicity screams taste, money and high society.
2 Tone Feather Swirl Sinamay Hat
This blue and white hat is more like an artfully gift-wrapped present complete with ribbons, feathers and flair.
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Black, White and Oh, So Chic
First off, I am a huge fan of black and white together, especially in the summer. Second, anyone will tell you that at the Derby, or any racing events, the black and white combo hats provide a hint of elegance and drama.
Glamorous Black & White, Ultra Wide Floppy Hats
Polk-A-Dot Brim Sinamay Hat
The intricacies of this hat are so amazing that it’s impossible to capture them in just one photo.
Lace Downbrim Hat
The official name implies the hat is woven with lace but the pictures detail so much more. The intricate design is full of unique beading and embellishments. The once casual-style hat is now Kentucky Derby ready!
STUNNING BLACK & WHITE TWO TONE CANVAS FLOPPY HAT
That’s right, this fun, funky hat is actually your basic canvas, floppy hat! But instead of just creating another reversible bucket hat, Luxury Divas added a fun twist to the brim to make it stylish and modern.
TROPICAL BLACK LINEN WIDE BRIM FLOPPY HAT
Linen hats tend to grow on trees here in Florida but I’ve never seen one like this around here. And I worked for a retailer that specialized in Florida-lifestyle hats for a while! The added dimensional swirls and fringe take this hat from tradition to funky.
Large Sinamay Knot Center Hat – Black
Snake Print Organza Hat – Silver & Gold
Solid Upbrim Reversable Hat
Detachable flower. Featured are the khaki and plum colors. Also available in red and black.
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Head Turning Colors
Reversible Wire Floppy JLO Hat
Jennifer Lopez is definitely the queen of the floppy hat trend. She brought the style back years ago and we flocked to it! She has a great collection out now that comes in a variety of bright summer-loving colors like fuchsia, lime, yellow and orange! The burn-out pattern all over the hat makes it fun to wear—but it’s also reversible!
LADYLIKE RED SHAPEABLE FABRIC FLOPPY HAT W/FLOWER
How can you not love a bright red, shiny hat with a flower that you can customize and shape to meet your mood? The brim bends, flips and molds so you can have a floppy hat one day and a derby the next!
Two Tone Shapeable Hat-Orange Flower
This peek-a-boo-pattern hat is fantastic! The summer orange shade would make any outfit pop! But the it’s the fun tropical print hiding underneath the brim that really makes this hat WOW!
Large Brim, Floral Print Sun Hats
These casual floppy hats add a pop of fun and color to any look. It would be fabulous paired with a perfectly tailored summer sundress and really hot, high-heeled sandals! They are whimsical, yet not over the top and could be worn all summer long! I’ve featured the white and the lime but it is also available in pink, red, black and natural.
Haughty-Haute Couture
I really thought I was done. I tried to be done. But it was so addicting that I just couldn’t stop looking at hats! And then right when I was about to go to bed, I came across this amazing place on Amazon.com called KaKyCo. Their shop was filled with hundreds of gorgeous headwear unlike anything I’ve ever seen. Unfortunately, most of the hats are actually wool and felt—which is fabulous come New Years Eve but not so great heading into the broiling hot Summer Track Season.
Don’t fret my fellow Hat-aholics, I did find a a bunch of other, non-wool super gorgeous hats for you to check out!
The Church Hats:
My family has never been overly religious but if I was told that I get to wear hats like this, I would be at church every Sunday! And probably Saturday night too!
Blue Satin Church Hat
Animal Print Church Hat
Peach Satin Ribbon & Beige Satin Ribbon Church Hat
Yellow Satin Ribbon Chuch Hat
The Metallic Hats
Winter Wool Felt Sinamay Combination Hat
I did have to throw in this one wool hat because it is just too darling and fab to leave it behind! Besides, it’s a Sinamay (the really lightweight, open-weave material) Wool Combo! It’s like the two balance each other out!
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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