The rundown:

Vintage Fair Isle bought at Trimingham’s in Bermuda

My go-to perfume

A classic watch c/o March Hare (20% off with FEWERBETTER20)

A perfectly slouchy bag to hold everything but the kitchen sink without looking ludicrously capacious (c/o Parker Thatch)

Vintage Ray-Ban aviators

The perfect slim-but-not-skinny jeans (c/o Frame; use FEWER15 for 15% off)

Chelsea boots

Notable: this Fair Isle sweater is more than fifty years old and still in excellent shape after years of wear. These jeans are ideal to update the 2010s interpretation of “prep”—I know I’m too mentally old to pull off the skinny jean the way I did the first time around! These are still slim enough to tuck into boots without being uncomfortable.

I’m always a fan of a bag that will really show its lifetime: the leather on this Parker Thatch bag will only get better with age. And, in this super-analog outfit, the Harriet watch and Eternity perfume brings us back to the 90s: you can almost see “You’ve Got Mail” emblazoned on the movie theatre marquee.