The Derby Look

I’ve never been to the Kentucky Derby.  Along with just about everyone, it’s on my bucket list.  It seems like a wonderfully debaucherous event, like a sorority formal for the post-grad set.  It’s completely acceptable to get overdressed, almost to a costume level, and get hammered on special drinks (mint juleps) out of special cups (sterling silver, bro).  I think there’s a horse race or something.

Anyway, I’d really like to go.  I’m all about experiences that are like no other, like seeing The Masters, bonefishing in the Bahamas, and playing Burning Tree.  I love seeing the crowd shots when watching on TV, as well as the coverage post-event.  Of course ALL of the ladies are beautiful, but for the guys: there are some big time winners, and some serious faux pas.  Personally, I wouldn’t deviate too far from my mean.  Everything I would pick is something I could wear to work or church the next week.  Since style is a serious part of the Kentucky Derby, and I’m a serious guy, here is how I would handle it:

From top left:

1. Custom Sport Coat in an exploding color/pattern:  While I’m not a costume guy, I do love the exploding jackets.  Going to the Derby would be a great excuse to add one to the arsenal.  This green silk and linen sport coat from Miller Brothers hits on all cylinders.
2. Read Wall X Thomas Mason White Spread Collar Dress Shirt:  You don’t want to look like some kid that snuck into the infield wearing some critter logo on his chest.  Get a nice shirt that will hold up to the day’s activities.  The oxford cloth is a good choice, and the spread collar turns up the heat on this dress shirt.
3. Persol 3019S Sunglasses:  These serve a couple functions: sun protection during the eight hours of tailgating, and to elegantly block the side eye.  You decide which is more important.
4. Rolex Cosmograph Daytona Gold Watch:  Pull out the big guns, just to use it as collateral when placing a bet.  Most likely you’ll be out of your element, and beyond reproach.  Keep Goldie on your wrist.
5. Col. Littleton No. 5 Cinch Belt in American Alligator:  The alligator leather puts this one a step above the rest.  The cinch keeps it tight.
6. Incotex ChinoLino Pants: Considering the event is in May, there’s a good chance that heat is going to be a factor.  Avoid wool.  A well cut pair of chinos will do the trick.  These from Incotex should be finished with the slightest of breaks, and a 2″ cuff.  The blend will give them a nice, worn look.  Don’t let them know it’s your first time.
7. Drake’s Silk/Linen Tie: I think I’m too old for ‘funny’ ties with beach chairs or something as cheeky, as I can stain grown up ties just as easy.  I don’t really wear bow ties, so I’d elect for a neck tie.  A really nice neck tie.
8. Monogrammed Linen Pocket Squares from Mark & Graham:  Pocket square slash sunglasses cleaner slash stolen by your better half because her mint julep cup is too cold to hold.
9. Barker Black Crown Loafers:  Instead of buying some overpriced jacket/suit/tie that you’ll wear once, allocate those funds to some serious sleds.  Barker Black loafers are as good as it gets, and the crown is the icing on top.  Show ’em who’s boss.
10. Fiddler Bourbon from American Spirit Whiskey:  While I love bourbon from up the road, I’m a Georgia boy, so I’ll let ’em know about some of the sauce we’re brewing down here.

And that’s that.  How would you do it?



  1. SMC
    04/26/2017 / 8:56 AM

    I’m getting to check it off my bucket list this year. Very similar choices, but I’ll go with bit loafers (since it’s a horse race) and a needlepoint belt. 

    • JRS
      04/26/2017 / 11:07 AM

      Lucky duck!  Bits and needlepoints are approved.  

  2. Alex J
    04/26/2017 / 9:21 AM

    Great look, very similar style from what I’ve done in the past couple years. Major points for going with a necktie instead of bowtie, wore them in college but ever since graduating I’ve always felt like I’m trying to hard with one.How would you compare the cut to other pants on the market? I’m in the market for some “more refined” chinos and those chinolinos always pop up in the conversation. I have some BB Milano fit twill chinos that have a nice fit, and I have always like J. Crew’s Classic Bowery pants. 

    • benny
      04/26/2017 / 9:47 AM

      Haven’t tried the Incotex yet – but if you want to get a more refined chino – check out the Unis Gio.

    • Ryan
      04/26/2017 / 10:31 AM

      Agreed. The bowtie is way over played. I have been guilty of wearing one myself.

      • JRS
        04/26/2017 / 11:09 AM

        The only time I wear a bow tie is at a black/white tie affair.  For me, bow ties have migrated to the ‘costume’ section of the sale rack.

    • JRS
      04/26/2017 / 11:08 AM

      Incotex are about as nice as it gets.  The Chinolinos are a cotton/linen blend, and I wouldn’t consider them ‘dressy’.  Look at their 100% cotton option, along with Epaulet, the Unis mentioned by Benny, or the in-house chinos at Harrison LTD (google them). 

  3. BCM
    04/26/2017 / 10:29 AM

    Wearing a heavily patterned jacket with a heavily patterned tie can get dicey real quick. Perhaps a more subtle tie in a complementary color to the jacket. Whatever you choose, check it out in the mirror before you leave just to be safe. I trust your style. 

    • JRS
      04/26/2017 / 11:10 AM

      Good call – and I agree.  I’d be sure to limit my bourbon intake prior to getting dressed…just to avoid faux pas like you mentioned.

    • nachdrock
      04/27/2017 / 6:14 PM

      Agreed but the combo above is perfect

  4. cRc
    04/26/2017 / 2:21 PM

    louisville, ky resident here and yes, you must attend but be sure to make it a two-day event by attending the oaks as well. i typically go with a silk/linen blend jacket, chinos, poplin shirt, bow-tie, needlepoint belt and gucci bit loafers. you will have an enjoyable time good sir. oh, and they are juleps not julips 😉

  5. Nem
    04/27/2017 / 9:23 AM

    Stylish choices.  That gold Rolex is gaudy, but I get your joke about collateral for wagers.  Make sure you check the weather if you ever actually do go to KY for the race weekend.  You’ll want that pair of Gokey field boots on if it’s wet. 

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