Kentucky Derby Style

So the famed Kentucky Derby is this Saturday, and admittedly, I don’t really know much about the horse race or it’s implications.  It seems that the race’s reputation is more centered around the atmosphere, the bourbon, and the style…and really – is there anything wrong with that?  Most of the guys look very dapper, save for the ones in costumes or the kids that throw every pastel into the blender and think it’s ‘preppy’…and all of the women look great, with their hats topping off hours of primping.

Me?  This is how I’d do it:

From top left:

1. Persol Suprema Keyhole Sunglasses:  First and foremost, the race is a chance to spend the day outside, so protect your eyes from the sun and make sure you are not caught staring.
2. J. Crew Ludlow Jacket in Italian Oxford Cloth:  Since it’s going to be warm, wear a jacket that will breathe a little bit.  J. Crew’s Ludlow stuff is about as good as you can get for the money…and this one is 30% off.
3. Southern Proper “Mellow Yellow” Bow Tie:  I’m not even a bow tie guy, but Emmie and Co. have really knocked it out of the park with the bold stripe options.  An updated take on a very classic style.
4. Mophie Juice Pack:  Since chargers aren’t available, bring your generator.  There are lots of pictures and texts to be had…and with our social media culture, if the event isn’t Instagrammed, did it really happen?
5. Salvatore Ferragamo Horse Print Silk Pocket Square:  You know, get in the spirit.  Horses on silk.
6. Ledbury White Fine Twill Dress Shirt: Classic and comfortable, the best base for the rest of your pallet.
7. Breitling Navitimer:  If you had any idea what all the numbers and dials meant, you’d be able to time the race.  No way that happens.
8. Sid Mashburn Navy Seersucker Sport Trousers:  A very dressed up version of seersucker.  The darker, well cut pants will give your look an updated style, and the seersucker will keep you cool.  Don’t worry about any bourbon spills, these can go in the wash.
9. Res Ipsa #11 Wool Loafers:  Comfort is the name of the game, and it doesn’t get much better than these.  Your shoes are a great place to show off your flare.
10. Basil Hayden Bourbon:  In my top two Bourbon choices.
11. Filson Oil Tin Wine Tote:  You’ve got to carry your bourbon somehow, and brown paper bags are so ‘grocery store’.  Be better than that.
12. Belle Meade Bourbon:  …and since there are two spots in the tote, add the other of my top two.
13: Martin Dingman Newport Belt:  Light blue, finely woven, and nice leather.  Sounds about perfect for a dressed up day at the track.

What are you wearing?

1st and 2nd Images: Google Image Search



  1. Tyler
    05/01/2014 / 10:08 AM

    Great list. Being a Kentuckian, I would however have to replace the Tennessee-made bourbon(Belle Meade) on the list with some more bourbon from our great state!

  2. Seth
    05/01/2014 / 12:06 PM

    Did you size up or down on your Ispa’s?

  3. JRS
    05/01/2014 / 1:28 PM

    @Seth – I wear a size 9 dress shoe, and am going with a size 9 in the Res Ipsas. They recommend going a size down, but it’s just a bit short for me. I’m going to put a pad inside.

  4. Seth
    05/01/2014 / 1:52 PM

    @JRS Thank for the input I’m ready to get a pair

  5. RayLRiv
    05/01/2014 / 1:58 PM

    I’d wear ANYTHING from Crittenden Gentlemen’s Clothing in Midway, KY (near Lexington.) Crittenden Rawlings spend 10 yrs working for Norman Hilton, 10 with Ralph Lauren, and Critt was CEO of Oxxford Clothes in Chicago. Critt retired from Oxxford and he and his wife Judy moved back home to Midway – but Critt came out of retirement to start his own line of gentlemen’s fine clothing. He KNOWS style.

    I’ll have to disagree with Number 7. I’m wearing my Omega Speedmaster Professional. Breitlings are an adequate fall back but I’m an Omega man (and a pilot.)

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