It’s either an exciting time or a dreaded time -or a little of both- for those of us who live on this particular part of the Ohio River…. when our familiar hometown turns into a raucous traffic jam all for the sake of 2-minutes of risky excitement.

Kentucky is known for a lot of things but undoubtedly the most famous is that esteemed five-letter word…..  DERBY!

Various festivities began a couple of weeks ago and conclude with The Oaks tomorrow and an unfortunately-predicted stormy Saturday for this year’s horse race.  And then there’s the parties.  And all-of-a-sudden, our relatively humble city is an unrecognizable imitation of L.A. (imitation being the operative word.  there’s enough beer-guzzlin’ , bare skin,  mud-fight, celebrity-stalkin’ to keep it at just that)

Personally, I enjoy it.  And what I enjoy most is getting dressed up in Spring’s best, and sitting ’round the TV at a friends house, drinking bourbon and mint juleps and making $1 bets.   And of course– commenting on the year’s most unique, flattering, interesting, and ostentatiously hideous adaptations of the most infamous Derby Accessory….  The Hat.

And so here– in anticipation– I offer you my own admittedly biased critique of this decorated tradition

(there’s stuff for the men too so keep reading boys)

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I should say first that Derby is a time when perhaps more than ever I say “More Power to You”.  Wear that Hat girl or let it wear you if you really want.  I like to be surprised in seeing something I might have called “Fugly” on its plastic display head sitting  glamorously on just the right ladies head.  But still – my natural affinity is for classy, sexy, moderately “safe w/ a twist”

First- I will always love the wide-brim  – both stiff and floppy.  It’s SOOOO classically dramatic – especially in a monochromatic or neutrally-contrasting color.  Only problem is I can never see anything from under it.

I also love the cloche as it’s much more versatile for every day other than Derby day.  This one on your left will fancy-up a simple dress while the one on the right is… well, it’s the most adorable thing in the world and I want one now!!

And these are the ones I wish I were bold enough to wear.  Alas- i am not.  But perhaps you are?

from NYfashionhats.com

One of the most popular hat ornaments is the feather.  And one of the most popular things to do with the feather is OVERdo it.  Way overdo it.  Instead, I encourage it to be used with careful instruction… as a small accent piece

or if you are just a Feather Fanatic, go knock yourself out but kick the hat habit and try a Fascinator instead.  I’m all about the bold & beautiful when it comes to these pieces

Do what you will, but if you do not keep to my guidelines you run a very serious risk of inducing children –and fairytale daydreamers like myself — to believe that you have shamelessly harmed a magical and endangered mythical creature in the making of your headdress.

Now men do not have quite as many choices it’s true, and frankly – they shouldn’t have.  The Fedora is Fine and all you could ask for.  Classic, subtle, and charming…  the Derby man is a Dapper man…

And ladies- if he asks to wear this…..  dump him! (’cause he’s likely up to no good in that infield anyways)

And back to the ladies once more…  If all-of-the-above is too much for you or you have a very oddly shaped head that requires strenuous and expensive custom-hat-tailoring… stick with the thousands and thousands of choices you have these days in hair-band embellishments.  I’m gonna recommend the below ’cause it comes from my dear friend over at Posies & Plume

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And now finally…  what Derby coverage would be complete without The Rich & Famous.  And keeping with our sartorial theme, let’s take a look at some major Dos & Donts starring some of our favorite gawk-provoking celebs from last year’s red carpet (pics provided from local paper CJ)

DO

Do follow that simple and classy w/a twist rule and you too could look as gorgeous and ageless as mother-and-daughter Jenner & Kardashian.  Kim’s hat is amazing btw.  Don’t you think?

As if we needed a reason to like funny men more.  Peaches, blues, and bowties CAN be used in menswear if the boy sporting it has the right personality to carry it and if they remember to ask one question… Does it resemble our gentleman-heroes of the past or does it resemble a clown on an off-day? (Or Andre 3000?)

Do Match your Mate but not too Much.  The midnight blues are romantically dashing on both sides for Bobby Flay and his wife, but playful stripes vs. elegant lace identify unique and personal styles.  Way to go.

Please Don’t

Don’t wear a stack of pancakes on your head or a…..  well, what the heck is that? a perfect prop for an improv routine, that’s for sure.  Oh brooke, brooke, brooke.

Do I even need to say anything? D.M.C better Run…. right back to his closet.  Guess somebody never got over the excitement of adding to their Hard Rock Cafe T-shirt collection.

If we can see where your belly-button is, it’s too tight.  And it looks like right after the magical mythical creature was killed, an especially tangle-haired smurf was the next victim.

Don’t!