2014 Kentucky Derby logo2014 Kentucky Derby

Kentucky Derby Hats: Best and Worst of 2014

Gabe ZaldivarPop Culture Lead WriterMay 3, 2014

Kentucky Derby Hats: Best and Worst of 2014

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    Matthew Stockman/Getty Images

    Some Kentucky Derby fans have been waiting a whole year to bust out their ridiculously large hats, so let's humor them and gawk in their direction. 

    It's time once again to enjoy the most exciting two minutes in sports, featuring a bunch of horses galloping on their much-ballyhooed run for the roses. 

    It's a time for fun, laughter, mint juleps and hats—a veritable cavalcade of crazy chapeaus. 

    Here is just a brief breakdown of the best and worst from the 2014 iteration of the Kentucky Derby. As you will soon see, even the truly awful are pretty darn great. 

Best

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    Andy Lyons/Getty Images

    If twerking were a Kentucky Derby hat, it would be on this lady's head. OK, that just sounds horrible, forget we said that. 

    Just concentrate on a sartorially sound decision that is both funky and refined. It walks right up to the line of absurdity and says not today. No, today we are going to rock this mother out. 

Worst

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    Dylan Buell/Getty Images

    Picking up this hat from a store created in our nightmares, this fan decided to honor Dance With Fate by dropping a head on the back of the hat. 

    This fan will see your cute pins and buttons and will raise you one haunting jockey face. The real question is: Where do they sell fake heads and how can I go my entire life not entering that store? 

Best

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    Kevin C. Cox/Getty Images

    Three, as it turns out, is a very good number—especially when you have young fans who understand that there is a difference between profound and ostentatious. 

    Each hat here is vibrant without being loud and classy without being outdated. 

    Bravo, bravo indeed. 

Worst

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    Dylan Buell/Getty Images

    So that's where I left my My Little Pony action figure. 

    We think, and this is just blind assumption here, the person under this hat is actually someone who was once featured on the show Hoarders and they just scooped up a portion of their house and tossed onto this hat. 

    There...there just can't be any other explanation. 

Best

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    Kevin C. Cox/Getty Images

    First off, this couple now has reached their limit of fedoras per crew, so hopefully there aren't any others lurking about. 

    Second, this is how you go to an event matching without being that annoying couple whose mere presence yields mass nausea. 

Worst

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    Dylan Buell/Getty Images

    Wearing a hat shouldn't necessitate constantly worrying about the vertical clearance of potential doorways. We are willing to give this hat a pass if it comes complete with a fireworks display, however. 

    It just has to. 

Best

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    Andy Lyons/Getty Images

    You simply have to see this hat rather than having it described, because rainbow polka dots on anything sounds like a recipe for disaster. 

    This one is a winner though. In all seriousness, we now feel just as happy as this lady wearing it. It could also be the bourbon kicking in. 

Worst

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    Andy Lyons/Getty Images

    Why didn't you go with the big one?

    We understand the homage to the "Run for the Roses," and we really quite enjoy seeing that theme play out in so many ways around the Kentucky Derby. But really, that is all just a bunch of words to avoid talking about this flowery faux pas. 

Best

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    USA TODAY Sports

    Sophisticated, classy and stunning: This hat is exactly what you should aim for when heading out to the Kentucky Derby. 

    You don't need anything bombastic and colorful to be the talk of the crowd. 

Worst

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    Dylan Buell/Getty Images

    "Honey, where did I put my hat? You know, the one with the depressed flamingo on the top...yeah, the one that looks like it wants to leap to its death from sheer embarrassment?"

    "Oh, never mind. I found it. It was right by yours."

Best

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    USA TODAY Sports

    Not only is this hat grand and colorful enough to garner notice at the Kentucky Derby, it's still compact sartorially to fit comfortably within smaller events. 

    Take this bad boy out to a picnic. Hell, take it out grocery shopping. The point is, get a lot of mileage out of this awesome hat. 

Worst

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    Dylan Buell/Getty Images

    In all seriousness, we think this costume is hilarious. 

    However, the horse looks like some weird equine/beaver/rabbit hybrid, which gives us the creepy kind of goosebumps. Points for taking a risk, but that poor thing needs to be put out of its misery. 

    We are talking about the hat. The guy can just go have a drink, perhaps more of what influenced him to buy this. 

Best

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    USA TODAY Sports

    Like a wallop of something delicious, this hat leaves you wanting more. It's like a giant refreshing dose of orange sherbet in chapeau form. 

    This hat probably weighs all of a few ounces but it packs a wallop that will stay with you all day—or at least a few more slides, but you get the idea. 

Worst

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    Dylan Buell/Getty Images

    Some people rake up their leaves and throw them into the trash; others save the foliage and create something they decide is wise to wear in outdoor settings. 

    You know, where people can see them. 

Best

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    USA TODAY Sports

    We will never look as good wearing something loud as this lady does with this rather audacious hat. 

    This particular decision comes dangerously close to disaster but pulls it off, which is roughly the opposite of any Rob Schneider film. 

    Perhaps one more feather here or a color decision there and we would have a horrible hat. As it stands, we have nothing all that bad to say. 

Worst

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    USA TODAY Sports

    It's like this lady went and stole the festive hat that Barbosa from Pirates of the Caribbean keeps for the weekend. Somewhere in fiction land, there is a very sad pirate. 

     

Best

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    Matthew Stockman/Getty Images

    Introducing Charm and Charminger. 

    Both hats combine for quite the breathtaking photo. And really, there isn't a great deal going on with these hats other than their perfect construction. 

    While others are going around with forests on their heads, these ladies are rocking some absolutely stunning hats. 

Worst

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    USA TODAY Sports

    We can take the grand hats some are wearing, even accepting some so big they probably take up a couple of seats in the stands. 

    However, we think it's best to leave the leftover Easter basket filler at home. 

Best

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    Rob Carr/Getty Images

    Look at this lady showing everyone how it's done!

    She went huge and loud and managed to pull it off with some fashion to spare. We don't even care what the rest of her outfit looks like, because she could be just a floating head and pull it off. 

Worst

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    Dylan Buell/Getty Images

    Someone took a wrong turn on their way to Mardi Gras and ended up at the Kentucky Derby.

    We are really searching for an overall theme here for the Three Amigos. We like to think these guys really spent hours deciding on their outfits, but really, we all know they slept in this. 

    The question best left unanswered is how they earned those beads. 

Best

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    Matthew Stockman/Getty Images

    We just had to fit one more best slide in for this dapper duo. We imagine this little guy leaves a group of people screaming "Adorable!" in his wake. 

    Folks, this is what slaying the Kentucky Derby looks like. 

Best of the Best

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    Bow before your fashion overlords. 

    No we just had to snap off an image of the Kentucky Derby's newest co-hosts, Tara Lipinski and Johnny Weir, both of whom looked awesome on Saturday. 

    Lipinski went refined as Weir went, well, Weir. Here are the two showing off their outfits, via The Big Lead

    Now, hurry up and cram these two in whatever you can next, NBC, because they might be sports' best one-two punch. 

Celeb Circuit: Scottie Pippen

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    That NBA Lottery Pick spotted this image fresh off Larsa Pippen's Instagram account, proving Scottie Pippen and his wife have serious game. 

Celeb Circuit: Tom Brady and Aaron Rodgers

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    This photo features Tom Brady not wearing a hat at the Kentucky Derby, which is the far less interesting version of the quarterback—we have found. 

    Brady and Aaron Rodgers certainly look awesome in their spring suits, but this wasn't nearly the best image from Brady's weekend. 

    The last couple of days were quite interesting for Mr. Brady who arrived at the Barnstable Brown Gala on Friday in a hot air balloon and showed up to festivities wearing a rather peculiar hat

    Thankfully, there is no evidence of dancing

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