What Do I Pack for a Three-Day Work Trip?
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You know the score. It’s a classic three-day, two-night work trip punctuated by meetings, working lunches, and dinners out. There will be handshakes, huddles, and pitches, early starts and late nights. You might get to visit the gym, maybe see a friend from college, or spend a free afternoon exploring a new city—but don’t bank on it.
Packing a carry-on to cover all the above is hard. I’ve spent the last decade trying to perfect it (with occasional success) and the one thing I’ve learned is that in this instance, personal style needs to be reframed through the prism of efficiency. Sounds dry but hear me out.
If you’re taking a flight, moving all day, jumping in cabs, going straight from work to dinner, you need clothes that can go reliably unnoticed through all of it. Looking cool is great, I spend most of my time trying to do it, but when it comes to clothes, “cool” is often a byword for uncomfortable, heavy, hot, or conspicuous—four attributes you don’t want from your outfit in this situation.
Unlike a vacation, packing for this category of trip requires military precision. You need a concise, multi-tool edit of uncomplicated, stylish stuff that can be mixed and matched to maximum effect, adapting easily to shifts in climate, schedule, and mood. I spoke to Mats Klingberg, founder of menswear boutique Trunk Clothiers (and a master of elegant business attire) on this very subject, and he had just returned from a trip that started in 10-degree Canada and finished in 90-degree St Barths. He took a single carry-on.
That sounds extreme, but the single carry-on is common among serious travelers. With this guide, you needn’t be a grizzled road warrior to adopt their hard-earned lessons.
The first port of call should be a suit in a soft, non-shiny fabric. The cloth is crucial because it needs to be comfortable all day and work when you break the suit into separates (more on that later). You could go for one of the many “travel” suits on the market—high-twist wool makes them water-repellent and wrinkle free—but unless all your time will be spent in the C-Suite, I’d recommend something in a cotton twill or textured hopsack, like this Thom Sweeney suit, or in a varied mix of cotton, linen, wool, silk, like this cotton-linen blend by J Crew. Navy is the logical go-to, and I’d avoid black or charcoal, which are both too drab. If you’re feeling bold, you might try a dusty green, or even a slubby brown. Neapolitan tailor De Petrillo would be good for that. Pack a travel steamer, just in case.
Next, a poplin shirt you can wear with a tie—I love the striped shirts at Budd—and then a more casual chambray shirt (try Sid Mashburn) that you can also wear with a tie, but that looks even better without one. In terms of the tie, a plain knit number will suffice. Nothing chunky and loud; you want simple and textured. British brand Percival’s woven linen ties are perfect.
You already have two looks, and we’re just getting started.
In terms of footwear, you need one pair that will work with everything. I’d opt for black penny loafers. I’m a Paraboot devotee, but you could also go with a chunky derby, either in brown suede or black leather. Another option: a great pair of chelsea boots, which would be handy at the TSA line. It’s up to you, but you just need a pair of shoes that won’t look mismatched with a pair of mid-blue, regular fit jeans, which you will also need to pack. These can come from anywhere, but Levi’s 501 is still pretty hard to beat. If you want a substantial pair, head to Orslow for 107s. Whichever brand you prefer, make sure they finish at or above your shoes and don’t puddle over.
Now you need an alternative to the suit jacket, which is where a good chore coat comes in. You probably won’t wear it with a shirt and tie, but it’s nice to have the option, and it will be more comfortable on the travel days. Brunello Cucinelli and Loro Piana make luxurious versions of the format. If you don’t want to break the bank, visit Mr Porter for itsMr P collection or Swedish brand A Day’s March. Milan’s Massimo Alba would be good, too.
Next, a white crew-neck tee, maybe two (or one in navy, or maybe even a vest to peek out from under the chambray shirt), and an open-collar knit polo that you can wear on its own or underneath the blazer. They’re great because they’re not as golfy as a classic polo, and right now you can find them everywhere. Abercrombie & Fitch do one with what they call a “Johnny collar,” but I’d point you in the direction of Sunspel’s fine rib silk-cotton polo, which is lighter and a little slicker. If it’s going to be chilly, consider making the polo long sleeve.
Now you just need underwear (three pairs, max), socks, and workout clothes. Be sparing with the latter, you probably won’t work out as much as you think. This is where your second pair of shoes comes in—if you can bring running sneakers that don’t look terrible with the jeans (such as Asics’s Trabuco Max III) all the better.
If it’s going to be really hot, you could opt for a suit in seersucker or a linen mix (pure linen will crease too much). Make sure it’s unlined. Officine Generale is great for warm weather suiting. And maybe bring an extra pair of lightweight pants and some swim trunks.
If the forecast says rain, pack a simple raincoat. Burberry still makes the best. And if it’s going to be really cold, you could keep the raincoat and add a quilted down or fleece vest underneath, or swap it out completely for a proper wool overcoat, like this one by Lemaire. Then pack a thick gauge scarf or a beanie (nothing too chunky or branded) but not both—they never look good together. Acne Studios is good for either.
Noew just the finishing touches. A steel watch would be good. I love the compact functionality of Tudor’s 37mm Black Bay 54, and the Mid-Century charm of Nivada Grenchen’s Super Antarctic (on a Twist-O-Flex strap, ideally.) You might want to pack a baseball hat, too. And you will definitely want sunglasses—for me, black acetate always—even if there’s no chance of sun. That red-eye home can be brutal.
How To Wear It
Traveling Out + Arrival Day: Jeans, Loafers, T-Shirt, Chore Coat + Overcoat/Raincoat. Comfortable enough for traveling, and if you switch the tee for a shirt, smart enough afternoon meetings and/or dinner.
Day Two: Suit, Shirt, Tie, Loafers, Overcoat/Raincoat.
Day Two: Suit Pants, Knit Polo/Chambray Shirt, Chore Jacket (if Necessary,) Loafers, Overcoat/Raincoat.
Day Four + Traveling Home: Suit jacket (switch to chore jacket at the airport), White Tee, Jeans, Loafers (switch to sneakers at the airport), Overcoat, Beanie, Sunglasses.
(Watch on at all times)
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