Post Kentucky Derby Style Thoughts


One day I’ll make it to Churchill Downs for the Kentucky Derby.  Mrs. RCS and I talked about it yesterday, and we both agree that it’s a bucket list trip.  NBC did their normal seven hours of coverage yesterday, which is great background noice for chasing around a 9 month old.  Honestly, #HJS really enjoyed the coverage as well.  Not because of the horses.  Not because of all the lady’s hats.  Not because of Johnny and Tara (who are a National treasure):

#HJS laughed harder than I’ve ever seen him laugh at what all the men were wearing.  Why?  For the most part, the vast majority of the guys with reserved seating looked like they were late for the circus.  What a shame.

The Kentucky Derby is one of the most sought after tickets of any sporting event.  The local airport ran out of parking for all the private planes.  The sell $1000 mint julips.  In terms of ‘dressing the part’, it’s more about subtlety than looking like a clown.  Notice all the owners and billionaires dressed like they ran the place, not like they were about to make balloon animals.

I know I’m not speaking to any Red Clay Soul readers, as I know all of you are a stylish bunch.  However, I understand the temptation to spread your sartorial wings.  Let me save you the hassle: DON’T DO IT.  It’s not worth it.  After you sober up and see yourself in pictures, you will be filled with regret.  You’ll hear things from your friends like “Man, you really went all out”, or “Hot pink pants are a bold move”.  Those are not a compliments.

The next Kentucky Derby is a year away, but let me get ahead of this and give some examples of RCS approved Kentucky Derby garb.  Keep this in mind: it’s not a costume party.  Don’t buy an ‘outfit’, and don’t try too hard.  Here’s my favorite look of the day:

This is what I would call doing it right.  Very appropriate for the Derby, with a hint of fun with the suede bucs and the Panama Jack hat.  Well done, Ty Burrell.

Here are some ideas for next year, in the theme of salsa (since the Derby was on Cinco de Mayo).  Note: these are not meant to be outfits, but examples of appropriate pieces to consider for your Derby look:

Mild Stuff:

Brooks Brothers Hopsack Navy Sport Coat:  It’s a navy blazer.  A good base to add some medium or spicy shoes (like those Res Ipsas) or a bold tie.
Onward Reserve Whiskey Tie:  A little whiskey theme should be right at home in Kentucky.  Good with seersucker or tan.
Salvatore Ferragamo Crown Bit Loafers:  Bit loafers are about as cool as it gets, and they essentially go with everything.

Medium Stuff:

Brooks Brothers Brown/Blue Windowpane Sport Coat:  Adding a little something extra to the look, like a cool windowpane sport coat with some texture.  Do this over a crisp white shirt and a solid tie, and you are in business.
Trumbull & Rhodes Isle of Wights Tie:  A cool floral tie that isn’t pastel.  This works great with a seersucker blazer or a solid tan sport coat.
Cobbler Union Noah V Suede Dress Shoes:  Suede derbys are super cool.  They are like race cars that double as shoes.  Suede is a power play, unless there is a downpour.  Check the weather.

Spicy Stuff:

Ledbury Beckwith Sport Coat:  If you must add color to your wardrobe, do it right, as in a jacket that you’ll wear outside of Churchill Downs.  Let this be the statement of the day.
Drakes Large Flower Silk/Linen Tie: This is what I think of when I think ‘spicy’ tie.  This floral has great texture, and would look great as the statement piece of an outfit.
Res Ipsa Kilim Loafers:  The definition of spicy.  A bold move that requires confidence.  There’s no need to go hard in any other part of your outfit: just go basic with a navy blazer, tan pants with little to no break, a solid shirt and a good tie.  Let the shoes speak for themselves.

For accessories, there’s all sorts of stuff you can bring, but it’s really about lugging it around with you.  I’d suggest going minimal, unless you have the option of storage (like a suite).  There’s also the infield considerations, which is a pretty hardcore environment.  You are completely susceptible to the elements.  It’s ‘Hunger Games’ in Vineyard Vines whale hats.  Anyway, here’s where I’m at:

1. Panama Jack Straw Hat from Colonel Littleton:  Of course you need a cool hat.  Don’t think too hard on this – a Panama Jack hat looks perfect in this environment, and you can use it as a fishing hat this Summer.
2. Persol Foldable Sunglasses:  Shades to allow some serious people watching.  You wouldn’t want to be caught staring.
3. Le Chameau Chasseur Boots:  Infield play: if there is any rain in the forecast, go ahead and boot up.  There’s nothing worse than wet feet all day.
4. Bandana:  Instead of a pocket square, pack a bandana in your pack pocket.  It’ll be much more practical for a seven hour fiesta.  It will also catch all of your tears should your horse lose.
5. Rain Poncho:  The said that it has rained during five of the last ten Kentucky Derbys.  Pack accordingly.

What did I miss?

Images:  Google Image Search 


1 Comment

  1. HL
    05/07/2018 / 9:55 AM

    I like this post. I like the idea of a little flare but it needs to be one piece (i.e blazer, bow tie or pants) I like the idea of slimmer pants, shorter inseam to wear loafers sans socks and a little ankle shows. A proper fitting blazer ( if the blazer is more of the spicy attire then just a shirt, if the blazer is more mild then wear a spicy bow tie. I also am a fan of watches so its a simple way for guys to show some wrist game action.

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