Although O’Brien assured me that he would never actually wear a garish fanny pack, he told me that he does travel with “fake beards, fake mustaches, and a weird Don Quixote costume,” which are all props that get sent ahead. But when O’Brien travels alone, he is left to pack his everyday clothes and toiletries, just like the rest of us.
Miraculously, he manages to fit everything in a single carry-on, thanks to his philosophy of underpacking, bringing versatile and comfortable multipurpose clothes, and sticking to a single color palette. “Pretend you’re Steve Jobs,” he suggested.
O’Brien travels with Away’s The Bigger Carry-On (incidentally, our pick for the best hard-sided carry-on) because it’s “pretty indestructible” and it “fits the most,” even if it may be too big for smaller planes.
Top pick
This great-looking, relatively resilient piece of hard-sided luggage is O’Brien’s go-to suitcase and a Wirecutter pick. It’s roomier than Away’s standard carry-on, though it may get gate-checked on smaller planes.
O’Brien typically packs two pairs of jeans, one blue and one black. And this “tends to take care of 95% of the situations you’d be in,” he explained. His favorite brand, Du/er, makes stretchy pants with a dash of Lycra.
“You could do yoga in these, but they just look like regular jeans, and they’re incredibly comfortable,” he said. (He was, in fact, wearing a pair during our interview.)
O’Brien says his go-to jeans are made from comfortable, stretchy, material (which is also designed to be moisture-wicking), but they look like classic denim. A blue pair and a black pair will cover most travel situations, and they come in a slew of cuts.
He pairs his jeans with a classic tee, like his favorite dark blue T-shirt from Sunspel. “It’s not a cheap T-shirt,” he admitted. But the shirts “hold up pretty well over time,” he said. “And they don’t start to look ratty. They actually look kind of nice.”
This classic T-shirt is O’Brien’s favorite because it holds up well over time, without looking ratty. It’s made with Supima cotton, which is known for being soft and breathable, and it comes in several cuts and weights. But it’s on the pricey side.
O’Brien also brings a dark blue, cashmere Brunello Cucinelli zip-up hoodie, which he’s had for years. “I’ve noticed that you can wear that with anything,” he said. “It can go to almost any climate, and you can just wear that and be a chill, relaxed dude headed down to the gym, or you can wear it underneath an overcoat, and, you know, you look like Sting on his way to the Grammys.”
But you don’t need a luxury version. “Literally, you could get [something similar] at Banana Republic,” he suggested. (We found this zip-up cashmere hoodie from Naadam, a brand that makes one of our favorite cashmere crewnecks.)
O’Brien loves this cardigan-hoodie hybrid because it’s made from soft cashmere that works in many climates, and it can easily be dressed up or down. It does have a luxury price tag, though.
O’Brien also packs a versatile dark blue suit from State & Liberty, which he said he likes because it’s made with stretchy, athletic-like material. “You can attend a funeral or enter a jujitsu tournament, and you’re set either way,” he joked.
O’Brien says his go-to travel suit is comfortable enough for jujitsu but sophisticated enough for a funeral. It’s made from a stretchy, blended material that includes rayon and spandex.
He stresses that for Conan O’Brien Must Go, his team will send some of his wardrobe ahead of time, including a variety of coats — take, for example, his trip to Norway in Season 1, where he wore a warm, double-breasted coat during a car breakdown in the snow and a bright yellow raincoat during a fishing expedition.
But when he’s traveling sans show to a cooler climate, he likes to bring one versatile coat, like his favorite water-resistant, blazer-like outerwear, which also has a lining. It works as a kind of raincoat and a winter coat, and it looks good no matter the setting. (O’Brien’s jacket is from L.B.M 1911, though the company no longer makes the same style.)
He also suggested bringing an “airline’s captain uniform to ensure early boarding,” but, personally, we don’t recommend doing this.
