Packing with Zach Weiss

Nobody moves through the world quite like international man of mystery Zach Weiss. Trying to keep up with his whereabouts will leave you dizzy—one day he’s cannonballing into the Hearst Castle pool, the next he’s watching snow polo in St Moritz, then dashing off to a party in Tokyo or Doha—and somehow always has the perfect outfit for whatever niche situation he’s in. If you’ve ever wondered how the hell does he pack for it all?—same. Luckily, we caught him in one place long enough to share his hacks for shipping things ahead, squeezing in one last swim (without soaking your suitcase), and avoiding cowboy faux pas at the airport.

What is your general approach to packing? How do you manage packing for multi-leg trips with different events and weather?

First things first: I do not subscribe to the “carry on only” lifestyle, and I’m never impressed by those who swear by it. They’re often preachy and a bit smug about it, too. Congratulations to you for saving 20 minutes at baggage claim!

Now that we’ve gotten that out of the way, I usually tackle my packing by making a Word document or note in my phone with an itinerary of things I should dress for, including any particularly important dressing guidelines to keep in mind, often for a wedding, such as *BLACK TIE* or *WESTERN FORMAL* or *OUTDOOR DINNER, BRING LAYERS.* If the trip doesn’t have a set itinerary, I break it up by picking one daytime and one nighttime outfit for each day, and try to take note of where I might be able to repeat a jacket or a pair of jeans to save room.

When it comes to actually putting the items in the bag(s), I start by separating my most valuable or irreplaceable items, and putting those in my carry-on roller bag—vintage clothes, jewelry, shoes, black tie. If there’s room left over, I try to put in one pair of underwear, one undershirt, and one full outfit for the day I arrive, just in case I don’t feel like opening my large bag and unpacking everything.

When I have multiple stops or climates strung together, I try to pack far in advance and use one of two baggage shipping services called SendMyBag or Luggage Forward. I check the price of the route on each, and go with the cheaper option. It basically just entails printing 3 documents: a packing list for the interior of the bag, a label to tape to the front of the bag, and a final set of labels and customs forms zip-tied to the bag’s handle. If you’re feeling weird about sending it ahead, add an AirTag in to keep an eye on its journey.

What’s your go-to luggage?

For my carry-on I use a duffle bag from MAS Brothers. Full disclosure, the brand gifted it to me many years ago, and I loved the way it looked, but over time I came to realize it’s the largest possible bag I’ve come across that could be considered a “personal item.” It fits under the seat in front of me when I’m in an economy seat, and it fits well on top of my carry-on roller bag so I don’t have to lug it on my shoulder through the airport.

For the carry-on roller bag, I use an old Rimowa Salsa trolley bag, which I scored during a press trip with the brand to Oshkosh, Wisconsin (that’s a story for another time!), just before they were acquired by LVMH. It’s an almost-hard-shell case with a little bit of squishiness, so I find it’s the best of both worlds and fits a lot more than the average carry-on sized roller.

If I’m really trying to be fancy, and I know I might be traveling with a group or encountering some folks right when I get off the plane, I use one of my small leather Globetrotter trolley bags. The only caveat when using one of these is that you need to be very, very sure you won’t have to check the bag due to limited overhead bin space. They’re too precious to be tossed around, but if you’re into nicks and scuff, go for it.

For my checked baggage, I use one of two Rimowa trolleys, which can take a beating and still look good. They both have the basic single clasp, not the hinged double latch, of which I’ve heard mixed reviews.

If I know I’m going to shop and need room for new items, I like the Victorinox Spectra collection that can be zipped open and expanded, or if I have a lot of soft winter coats and accessories to bring with me, I have a beat-up rolling duffle that never fails me.

How do you approach the basics?

In addition to socks, underwear and undershirts, I have a few core things that I know I’ll wear on every trip: White jeans from RRL for no stretch but better fit, or Brooks Brothers for a little bit of stretch. Always white denim. Then navy trousers, a plain white button-down shirt, a striped button-down shirt, a navy turtleneck, and brown suede loafers. The brown loafers are either off the rack brown suede George Cleverley penny loafer with a small heel, or for no heel: the Emporio Sirenuse brown suede slipper. I also always try to remember to pack a black silk bowtie and bathing suit, just in case. I find that Thorsun and Frescobal Caraioca suits dry the quickest. Vilbrequin has fun patterns but they’re a bit slower to dry.

If I’m packing anything particularly bulky like a big overcoat or a chunky sweater, I try to make sure I’ll wear it at least twice to make it worth the space.

Are you a roller or a folder?

I fold, unless I am truly trying to cram everything in, and then I resort to rolling. It’s more efficient, but it’s an extra step I don’t always take. During a safari trip to Botswana last Thanksgiving I was limited to one duffle for 10 days. That required some creative rolling and repeating.

Any other packing tricks or hacks?

Bring a waterproof nylon swimsuit bag, or a few large plastic Ziploc bags, in case you go swimming the day you’re departing and don’t have time for your swimsuit to dry. One last swim is a great sendoff on a trip, and bringing one of these simple bags makes it that much easier to enjoy.

What’s your shoe strategy?

I lean heavily on one or two styles of brown loafers, and I go through my packing document to make sure they pair decently with each potential outfit. If I see an opportunity for a more fun and interesting pair of shoes, I follow the same “bulky item” rule and make sure I can wear them twice or more on the trip to rationalize the space and weight they’re taking up.

The one mistake I used to make, mostly due to my ego but also as an attempt to save space, was wearing my cowboy boots in the airport. I love when the airports in places like Texas and Colorado have a bootjack available for you to get them off, but most airports don’t offer it, and you end up looking like a fool trying to get your boots off. Not the most cowboy move.

Do you have a great travel hat?

I usually go for a baseball cap in the airport. I’ve amassed a couple hundred from hotel shops and dive bars and gift bags, and they’re always an easy accessory for the road that I don’t feel bad beating up. My hair’s also too unruly to get off the plane and greet someone, potentially a new acquaintance, without a hat on.

The one thing that always drives me crazy, and also in the cowboy category, is when I have to travel wearing a cowboy hat. It’s cumbersome and prohibits you from putting your head all the way back on your seat, so I try to avoid it at all costs by making room for it in my bag or shipping it ahead. If I don’t have any other choice, and need to wear the hat for the sake of space in my bag, I make sure I don’t wear sneakers. A man in a cowboy hat and sneakers just looks goofy.

How do you think about accessories?

My accessories are minimal, but I’m a big collector of sunglasses, so I bring one pair or more for each day I’m away so I can switch it up. I lay them all out in an effort to resemble Elton John’s sunglasses closet (Google it!), but my room usually just ends up looking like a Sunglass Hut. I have yet to find an elegant and efficient way to pack them though, so if you have any ideas please share them with me!

What’s always in your Dopp kit/toiletry bag/pharmacy kit?

The obvious things—toothpaste, toothbrush, deodorant—none of which I’m precious about. After trying every boutique-y brand and venture-backed DTC “disruptor,” I’ve retreated back to the big box, Proctor & Gamble types.

If I splurge on a shipment of it, my friends Bari Baz and Saralynn Feinberg recommended two supplements you mix together in water, LivOn Laboratories Lypo-Spheric B Complex and Glutathione. They taste terrible, but they make you feel great, even if they’re a total placebo.

I just found these small pain relief patches in Tokyo called Nichiban Roihi Tsuboko; basically a cooler, smaller, international version of an Icy Hot patch.

I use the IS-Clinical Cleansing Complex, recommended to me after I saw the great facialist Cynthia Rivas.

I don’t always remember it, but I love when I have a bottle of Downy Wrinkle Releaser. It’s just fabric softener that saves you some ironing or steaming time. If I forget it, I just hang my clothes in the bathroom and run the shower as hot as possible with the door closed.

I bring a new Kaze face mask just in case I’m next to a sick person, and know I don’t have time to get sick when I get to where I’m going. I learned my lesson next to a sick kid on a flight last year who seemed to be parading his pneumonia around for everyone to enjoy.

On a plane, what essentials does your carry on bag always contain?

Eye mask, over-the-counter non-prescription sleep aid, glasses and contact lens stuff, chewing gum, two pairs of wireless headphones (one over-ear and one in-ear, you can swap them out when one dies on a long-haul flight), and one pair of corded headphones if you want to watch a movie on a cheap airline that won’t give you free headphones.

If I’m on an overnight flight, I bring a pair of thin sweatpants from Vuori that pack down to almost nothing. I put them on in the plane bathroom after we take off, and change back into my trousers before we land.

Any wisdom on traveling with electronics?  

I try to isolate all of my cords and converters into a small zipper bag inside my carry on. They always end up in a tangled mess, but I find it’s better to contain them than have them all over the interior of your duffle.

I’ve recently gotten hooked on the over-ear AirPod Max headphones, and if I’m traveling alone I put them on from the moment I get through airport security. They’re especially great to wear when boarding the plane to avoid anyone asking you which group number you are.

My laptop goes with me everywhere. I’m a bit of a boomer in that I bring it with me everywhere more so out of fear that I’ll need it to write something long form or to complete some task that can’t be done on my phone’s browser. I aspire to be an iPad person one day, but I’m not quite there yet. A boy can dream.

Do you have a travel uniform?

I wouldn’t say it’s a uniform, but I’ve found that I prefer some combination of…A lightweight piqué polo shirt, baseball cap, a chore coat with front pockets for easy access to my passport, wallet, and AirPods, a hooded sweatshirt over my shoulders to put on during a cold plane ride, with the hood for extra noise muffling. It can also be folded into a pillow. A pair of jeans with a bit of stretch in them or roomy trousers. I also never fly wearing shorts or wearing shoes without socks!