It always starts with a jacket, doesn’t it? So many good and strange adventures do. Let’s start with that jacket — a sport coat — because while you’re hopefully not intending to steal a shipping heir’s identity, you very well may be getting ready to travel.
Perhaps to some small, idyllic coastal town in Italy? Let’s assume so.
You’ll need a few different types of button downs. Just a few. Tom Ripley was fine with the same shirt re-washed for the whole first half of his trip, wasn’t he? You could be, too. But you might want to consider something extra light with short sleeves for your loose linen pants and floral shorts, something oversized and white to wear as a coverup on the sailboat, and something that you can tie at your belly button for afternoon apéritifs — you know, that goes with those flowy mid-calf skirts and espadrilles.
You need espadrilles. How silly of me to not have mentioned that by now.
I also suggest a pair of white-soled sneakers (you’ll learn to sail), loafers for the cobblestones and a very fancy pair of heels just in case you hop over to Rome for the opera.
…In which case, you’ll need earrings that work just as well with a swimsuit as they do a gown — for once you’re back on the beach, where you belong, relaxing by the water with a book and a basket. That basket’s going to carry your bread, your towel and your secrets, by the way.
Speaking of secrets, you’ll need a cashmere wrap to shrug them off. You’ll want tortoiseshell glasses to remove when reality needs blurring. Cat eye sunglasses for Vespa riding. And you’ll require a great knit to keep you warm on cool evenings while you sit outside to type. (Letters to home or ideas for that book you’ve been working on. Either option is equally as cryptic!)
A scarf would look great on you. And I think you could pull off a beret. You’ve been listening to a lot of Chet Baker, right? You can pretend your beret is your equivalent of a porkpie hat. Capris will feel wrong at first but they’ll work overseas, and I know a trench feels mom-ish but isn’t that perfect since you’re traveling under her maiden name?
Just avoid an incomprehensible web of lies and you will be more than fine. You’ll be divine! I’d simply be careful of whose jacket you borrow.