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Kentucky Derby Hats: Best and Worst of 2013

Gabe ZaldivarPop Culture Lead WriterMay 4, 2013

Kentucky Derby Hats: Best and Worst of 2013

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    Hats, everywhere hats!

    The 2013 Kentucky Derby will come and go in the blink of an eye, but the fashion taking over Churchill Downs will be burned into our brains for an eternity. 

    Of course, we mean that in the best and worst possible manner. Presented for your consideration are the more polarizing hats being worn around the 2013 Kentucky Derby. 

    So many women headed out to be noticed, and it certainly worked. Of course, this is just the start of a beautiful debate. I don't claim to be the lone voice in sartorial decisions, merely the one willing to jump-start the discussion. 

    Now, can we talk about these hats? 

Best

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    I could train for decades, educate myself on the latest fashions and have the all the money in the world, but I would still never come close to looking as classy as this lady is with the perfect hat for an otherwise dreary day. 

Worst

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    Rain muddied up the track, bringing sloppy conditions for the Kentucky Derby field on Saturday. It also mandated that some perfectly grand hats were covered up with everything from ponchos to trash bags, making for impromptu hat protectors. 

    As you will see, some were content to show off their style no matter the weather. While there may be some perfectly fine and classy hats underneath, the plastic-bag look isn't about to catch on. 

Best

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    There might be a debate as to whether fastened berets are actually hats. As you can tell by some of the entries on this list, we are quite liberal with the term. 

    In this case, we love it. 

    If you want to know how to wear a small but grandiose piece of fashion and do it with sophistication, check this lady out. On a rainy day, she manages to pop. 

Worst

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    Well, that's unfortunate. 

    While we could certainly throw this into the worst pile simply for what seems to be classy tuxedo shorts, the hats presented here are enough to do this couple in. 

    As for the man on the left, I am very interested to hear which hats he felt were a little too over the top. There is a very real piece of fashion out there that this go-getter felt was a bit too much for Churchill Downs. 

    As for the Mad Hatter on the right, her poor choice gets a free pass, only because it looks absolutely pleasant next to the tower of roses next to her. 

Best

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    Black may be safe on any other day, but the Derby is all about vibrant colors and audacious fashion. Still, there is something to be said for a muted color that can still draw the eyes, and do so in the right way. 

Worst

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    Unfortunately, the English language has not yet evolved enough to have proper adjectives to describe this mess. 

    Our derby fan here thought long and hard about which direction to go with their hat. In the end, she decided to go with all of them. This hat comes from stuffing every last idea in the world into one hat, even My Little Pony. 

Best

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    Go big or go home. 

    That sentiment is key to the annual Run for the Roses, and this lady epitomizes that perfectly. I have absolutely no idea what's on top of that hat, but I don't care. 

    Sometimes you just have to have faith. 

Worst

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    I am not sure if this is actually a hat of a flamingo that blew up on this poor lady's head. If anyone is missing a once proud and beautiful pink animal, we found it. 

Best

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    As if taken from a garden party from the set of Downton Abbey, this young woman chose a color and style that fits her perfectly. 

    I wish I could say the same for anything I've worn...ever. 

Worst

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    Under that enormous homage to the Kentucky Derby is a woman who thought this hat was a good idea. 

    I am all for a good bit of "wow factor," but I have to draw the line at having a fake head on your hat. We have to have some order and decorum. What's next, an actual jockey on your hat? 

    Well, I guess they are small enough. 

Best

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    Oh, this hat walks such a thin line. 

    As it were, the white hat has just enough size and flop with a nice punch of color, getting an added boost from the peacock feather. 

Worst

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    OK, I was very close to sticking this masterstroke into the best pile, because it's not only useful but topical. 

    The rain came pouring down at Churchill Downs, and this guy scrambled for the perfect hat for such an occasion. Still, it's ugly. There, I said it. 

Best

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    We get a two-for-one in this image of these ladies doing hat fashion correctly. 

    Both hats are the perfect size for Churchill Downs. That is to say, they are big and lavish while not dominating the face or presumed outfits. 

    These are hats that have you walking just a little taller and with a bit more pep in your step—even while walking the wet grounds on Saturday. 

Worst

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    You have to love the derby. It provides the perfect opportunity for people to bust that hat with the two fake flamingos on it out of their closet. 

    Really, a hat like this demands to be seen—but only briefly, because it is now burned into your brain for all eternity. 

Best

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    Boom. 

    As we said before, some of these hats are so close to being disasters that you just have to applaud the confidence here. 

    This easily could traipse into the pile of regrettable hats, but it instead works wonders for the woman who decided to purchase it and pop it on her head. 

    The brim pulled away from the forehead draws attention to the face, helped by the vibrant flower sitting just above. This lady was no doubt noticed, but for all the right reasons. 

Worst

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    This genius took the propeller beanie to the next logical step and delivered the interactive hat with spinning horses. 

    I have never seen more depressed fake thoroughbreds. 

Best

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    Elegant much?

    While some images don't offer the full picture of how these hats pair with the rest of the outfit, we get a true sense here. 

    This Kentucky Derby fan worked hard to select the perfect outfit that brings elegance and sophistication without entering the unfortunate realm of boring. 

    The hat manages to pull it all together. 

Worst

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    Bros will be bros. 

    We certainly admire the passion and disregard for the weather, and even have a soft spot for the amount of red, white and blue presented. Hell, we might even give a pass for those leggings in the middle. 

    From the jockey helmet to the Lincoln top hat, we have to ask these bros to go back and try again. 

Best

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    I feel bad for this poor girl who looks like she is either very bored or extremely tired of all this rain. Someone should inform her that she has the distinction of wearing one of the best hats of the day. 

Best

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    You don't wait months for the Kentucky Derby only to hide your outfit and hat under some plastic bags. This lady threw caution to the wind and walked around in the rain with her gorgeous outfit. 

    And we are very glad she did. Hiding under that coat is a dress that matches perfectly with that hat. A very slow clap is in order. 

Finish Line

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    Michelle Beadle has the last word of sorts in the fashion department. Here is an image she posted to her Twitter that features Redskins star Robert Griffin III and a couple of new besties. 

    It wouldn't be the perfect image to end the show if it didn't include some fantastic sidling up to the truly unfortunate. 

    Let's just say Beadle and Griffin are dominating things. 

     

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