The one and done horse race dress up

I had the distinct pleasure of attending my first Kentucky Derby a few years back. It was everything I could have expected and then some for such an historic sporting event.

This year I’m attending the Kentucky Oaks Day celebration at Churchill Downs. It is held the day before the Kentucky Derby and is the fourth highest attended horse race in the United States—after the Derby, the Preakness Stakes and the Belmont Stakes.

I’m not much of a gambler, but as at the Derby I was fortunate enough to attend, I will plunk down some of my hard earned money on horse(s) yet to be determined.

Part of the fun, or stress, in my case, and quite possibly for other men attending Oaks and/or Derby days is the wardrobe selection process. I’ve never been a clothes horse (sorry, couldn’t resist), but for galas such as these, you want to do it right.

I opted for a classic pink shirt, blue sports jacket, gray slacks and lightweight, charcoal gray fedora. And may I say it was not easy getting there. Well, it probably was, but choosing attire I wear most likely only once is not something a guy can practice for.

The fact you only get one chance, especially when you order some of your wardrobe online, only adds to the pressure of getting it right come (for me) Oaks Day.

I’m hoping the shirt is the only glitch I have as I just put to bed the online order for a bow tie and fedora.

I had to have my wife measure my head. I know it’s big. If just one person out of a hundred pays me a compliment anytime or place, my head size ends up increasing one whole size, too. Strangest thing.

This would account for the multitude of different hats in my closet ranging from medium to X-L sizes. Really, what other explanation could there be that would justify the variation in size?

Anyway, the hat is scheduled to arrive the day before The Oaks. Good thing I like it when things go down to the wire. Dang, another horse racing reference (I’m enjoying myself here today in case you haven’t noticed).

I have the sports jacket and trousers in tow (not exactly a horse racing reference, but still, if you think about the trailers the horses are transported in…).

The first go ‘round on the pink shirt was an epic fail. It was an online order of course. I selected a slim fit variety of an Alberto VO 5 (not the real designer, name changed to protect the innocent) designed shirt.

I would not characterize myself as broad shouldered but I’m spacious in the chest and my mid section has filled out some over the years.

The last slim fit shirt I purchased was one made by Van Hebarobber (again, not the real shirt company name) and it actually fit perfectly.

Now, though, fresh on the heels of someone who paid me a compliment by calling me handsome after seeing me dressed up (some) recently, not only did my head swell, but so did my upper body and arms.

The slim fit shirt was not a good fit. It was too tight and the length was too short to keep the shirt tucked in to my slacks every time I bent over to pick a penny off the pavement.

I returned it but not before I gave my better half a fashion show. She gave me her inimitable two thumbs down gesture of disapproval.

I almost flexed, doing my best Lou Ferrigno as the Incredible Bulk, I mean, Hulk, but I was seeking a refund on the shirt, not total destruction of it.

I set out shopping anew online for another pink shirt after sending back Virginia Slim for a refund.

I received the new regular fit shirt in the mail and it couldn’t have fit better. Now, I’m hoping it will survive the “easy wash/dry” experience I’m giving it—gentle cycle all the way as I want the buttons and thread intact after cleaning.

The trousers I already have, so nothing to worry about there.

Same with the sports jacket. Or is it sports coat? Or blazer jacket? Coats sound like they would be heavier and not breathe as well as something called jackets. Now, blazer jacket (or is it blazer for short?) is not on my radar simply due to this air of ambiguity.

Shoes and belt are already accounted for.

The final item that is producing some last minute sweating is my fedora which I just ordered.

I was warming up my gambling feelings as there are no reviews whatsoever for this hat. It was described as black but the pictures most definitely were more on the gray side. To add insult to injury I had to pay $12 extra to have it delivered the day before Oaks.

The least stressful wardrobe work-through was the bow tie.

Again, with the help of my personal wardrobe assistant, I was able to make a color-scheme appropriate choice. I do know how to dress myself, but for special occasions such as these, I like to leave as little as possible to chance.

The bow tie comes one-size fits all. It’s pre-tied, too, (don’t judge), so I won’t have to relive the trauma of watching YouTube videos explaining how to tie a bow tie. I thought I had it down on my dry runs before the Kentucky Derby, but on the day of, it took me a good twenty minutes to get the deed done—including a dastardly finger-numbing bout of carpal tunnel.

If not for the help of my personal wardrobe assistant once more, I would not have made it. I am, however, still emotionally scarred from the self-imposed bow tie tying deadline I endured.

This time, though, my bow tie experience will be much easier (fingers crossed).

If only it wasn’t a one-and-done type of wear affair.