Q: If one were lucky enough to own, hypothetically speaking of course, a horse that were talented enough to qualify for the Kentucky Derby, what could one wear in so far as footwear that would be appropriate? Would, say, Santoni double monk straps sans socks be too ridiculous? Hypothetically speaking, of course.
A: It's the Kentucky Derby, not the Kentucky Loafer. You could be wearing a pair of live flaming kittens on your feet — no one's going to notice. The Kentucky Derby is all about hats. Hats that would make Princess Beatrice say "What the fuck is that on your head? A designer extension cord? A pterodactyl's vacation home?"
Now, about those Santonis. The degree of difficulty is obviously very high, and unless you're a clotheshorse with a very good pedigree, we recommend them only for occasions where the collective blood alcohol level is .10 or higher. But that's exactly where you're headed, so we say go for them. Spending $1000 on shoes to wear in a setting where they're guaranteed to get overlooked takes senseless lack of utility to a level that makes us want to put a tiny replica of Churchill Downs on our heads, just so we can take it off to you.
Good luck on Saturday.
Earlier: Spring/Summer Looks. MB Endorses: Exposed Ankles
Earlier: Ask the MB: Kentucky Derby