Every year, around this time, we get a flurry of travel-specific questions. Whether it’s how to pack for a specific destination (Paris, Rome)… how to pack for a summer sporting event (the US Open, Wimbledon, the Kentucky Derby)… or how to dress for the actual journey (In-Transit Dressing). But a common refrain is that no one wants to check a bag for their trip.
And we get the appeal of traveling light. In fact, as it turns out, Sid is in Italy right now on a two-week trip to visit factories… with, you guessed it, only a carry-on. 14 days, one suitcase. And since he’s on the road (wait, we mean the Autostrada,) this month’s column is going to be more of a show than a tell. He’s in Sicily – mostly business with a little pleasure squeezed in – so this stuff is taking him to factories, meetings, showrooms, dinners, and the beach. What better time to show you how it’s done?
Here’s what he packed, and here are his hacks.
The Shirts
The Ties
Everything Else
The Shoes
The Extras
Hack 1: Wear one of your sport coats on the plane. Seriously – the high-twist wool Ghost is lightweight and resilient enough to look great even after a transatlantic flight. I wear it almost every time I fly. Pack the other one in a garment bag, fold it in half (“hamburger style” in elementary school parlance, or top to bottom) and tuck it in your suitcase.
Hack 2: This isn't for everyone, but I can get 2-3 wears per shirt, so it’s worth the time for me. Before the trip, I get them washed and folded at the cleaners, which makes them stack nicely in the suitcase. Oftentimes I’ll put them in their own nylon zip bag, but not necessary.
Hack 3: Don’t be afraid to do a little DIY laundry... in fact, you definitely don’t want to wait til you’re home to deal with stains. I spilled olive oil on my blue cellulare shirt this weekend and Ann got it out with the hand soap in the hotel bathroom. She’s unbelievable at stains. Anyway, I wore it again and it was as good as new. One week in and that’s the shirt I’ve worn most so far.
Hack 4: When you’re assembling your lineup of jackets and shirts, make sure ALL combinations will work together and that you feel good in them. Every shirt should go with every jacket. Solids and small stripes are a pretty sure thing for the shirting, solid and a check for the jacket.
Hack 5: This isn’t much of a hack – in fact, it’ll probably bum you out – but I recommend bringing one pair of shoe trees to keep in the pair you aren’t wearing on the plane. Heavy, but necessary. That’s what you gotta do when you invest in your shoes. Like the sport coat, I recommend wearing one of your heavier pairs of shoes on the actual flight so it doesn’t need to take up space in your suitcase. Loafers are an easy-on-easy-off through security, too.
Hack 6: Alright, this is just a reminder, so maybe we should have called these tips. Always bring something to swim in. You never know. On this trip, I had a long weekend with Ann, so it was always in the plan, but I’ve learned this lesson the hard way a few times so now I always bring a pair of swim trunks. I brought the neon yellow pair from a few years ago, but the green we’ve got now is pretty fantastic as well.
Hack (tip?) 7: In that same vein, bring a sweater. Even in the summer, nights can get cool and fine-gauge cashmere is lightweight enough for all seasons. (And if your hotel bathroom laundry efforts are unsuccessful, a sweater is a great way to cover a spot.) You won’t always need it, but when you do, you’ll be happy you spent the extra space. Mine is a purple one from last season but the blue Escorial would be exxxxxcellent as well.
Thanks y’all. Signing off from Sicily.