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?