Introducing Uncle Digby: Country Club Prep's Preppy & Spiritual Guide

He was kicked out of one prep school, two colleges, and three marriages. But he's our Uncle Digby, and we love him — at least most of the time. 
Uncle Digby
Pictured: Uncle Digby pondering the repp stripe.

Despite his wicked ways, Uncle Digby is a proud defender of preppy tradition. And so it only took three mint juleps to convince him to write an advice column where he could opine to his artery-clogged-heart's-content on all matters of style and decorum. 
And so with a great deal of pride (and the green light from our legal team), we're proud to introduce the Ask Uncle Digby column. Questions may be submitted in writing to

Uncle Digby,

I love the nautical trend, but I'm landlocked and get seasick on pool floaties. Can I wear sailing motifs without looking like a hopeless landlubber? 

Terra-Fied If Not On Terra Firma
Great Plains, USA


My dear, do you think all those '80s preppies in Top-Siders knew their starboard from their portside? Or those kids last year who caused the Bean Boot shortage had ever been duck hunting? 
It all comes down to intention. Imagine being tried by a jury of your fashion peers (you will be anyway). If there's no intent to defraud, then you're in the clear. Lighten up and think of it as style more than statement — as in member of the local yacht club. You don't have a local yacht club, anyway. 
If the thought of sporting anchors and nautical flags still makes you queasy, then steer towards basics, such as classic blue and white stripes.

Digby's Trivia: The word nausea comes from Nausicaa, a character in Homer's "Odyssey" whose name means "burner of ships."  

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