From the designer: Ten tips on packing for trips
Brian Spaly — February 6, 2009 @ 5:11 pm
Our customers travel a lot. Business trips, wedding weekends, jaunts all over the world to see friends and family and sporting events. Over the last 10 years I’ve come up with these 10 strategies for traveling sharp:
1. Pick a theme or color scheme for the trip and stick with it. Pick one great outfit and then build a few variations on it; hold the shoes, belt, and trousers constant and bring a few different shirts or sweaters. Whether the theme is black and yellow or navy and pink, make sure that everything works well together. As always, the more aggressive the outfit, the better. When’s the next time you’re gonna be in Haiti/Hawaii/Houston/Hebron?
2. Sweaters are elegant. Rock it simple and high-end, preferably a black, navy, or charcoal cashmere v-neck or crew neck. Sweaters can be rolled, worn around the shoulders to establish credibility with the jet set and signal you are a man of leisure, and are just plain easier to work with than dress shirts when on the road. Bring a few lightweight, soft cotton t-shirts to wear underneath and you are golden.
3. Accessorize. Invest in and travel with cool hats, sunglasses, sneakers—often the details make the outfit and allow you to do more creative stuff with your basics. It’s easier to pack a cool pair of shades than a second pair of jeans, and people are much more likely to notice your smooth accents than a different shade of indigo.
4. Get a cool weekend travel bag, and find a stylish larger rolling duffel/suitcase for gear-hauling ski trips and international excursions. Frame backpacks are for hippies and people that are going to be sleeping in the wilderness. You don’t need to be Kan(ye) the Louis-Vuitton-Don, but you should be if you can. Find a stylish overnight bag for shorter trips. You want something that says to the cab-driver or friend that picks you up at the airport this guys is legit, has all the right moves, and is probably on his way to a great party or an important meeting, perhaps to discuss a club-opening or a contract to play first base for the Chicago Cubs.
5. Go long on the small stuff. Bringing a few extra pairs of underwear and socks doesn’t take up much space. Fashion commandos do not require underwear at all. We’ve all had to free ball the plane ride home once or twice, but it’s preferable to have extra refreshments in this department.
6. Lightweight, zip-up track jackets/sweatshirts/hoodies are great for travel. Especially if they have two front pockets that close. These are extremely convenient for tickets, phone, 
music player, etc. Be aggressive—you want to look sharp when you take that middle seat next to the cutie in the window on Southwest…. The hipster zipster can also be a good way to camouflage your corporate origins when traveling for business (more on this topic in a post coming soon).
7. Be resourceful. If you bring gym clothes, most good technical shirts and running shorts can be washed easily in the shower and will hang dry in hours. They can be worn again day after day. Workout shirts and socks are good undergarments while in transit on the plane/train—they don’t need to be fresh clean when you work out in them later in the trip. Use that iron in your hotel room to make a good outfit look much better in under 10 minutes. It also enables you to pack wrinkled shirts and trousers and know that you can freshen them up on site.
8. Pack light and shop a bit on your destination. Especially when traveling abroad, leave space in your bag and plan on getting some fresh duds on location. Wear immediately to blend in with local hipsters, or replace outfits you destroyed at incendiary dance floor outings or impromptu Hyde Park rugby scrums.
9. NEVER, under any circumstances, is it okay to wear pants that have zip-off legs. Ever. If you own a pair, return them. These are truly a fashion disaster. Do not donate to charity—it’s not charitable.
10. Give things away. If you are staying at a friend’s house, and he compliments your impeccable taste in rugby shirts or hipster zipsters, leave the celebrated article as a host gift. Nothing in fashion is more noble than sharing your style with your best friends.
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great article!I am always looking for better ways to pack. Packing for trips the wrong way can lead to disastrous results and lots of money spend on additional crappy luggage that could have been put to good use by buying a new pair of Bonobos for example.
What stylish overnight bags would you recommend?
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I must admit, I have pants with zip off legs! I only wear them on long hiking trips. It sure isn’t fashionable, but it’s practical for the unpredictable weather in the mountains!
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Awesome piece. Strangely, I’ve adopted many of these suggestions over the years from pure laziness–I hate carrying a heavy load when heading to a destination (I tend to pack light, and tote garb that’s easily mixed and matched), and I leave enough space to pick up items from in my destination…local flavor is always good.
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jeans…on bonobos? crazy
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I was thinking the same thing Matt. Can someone photoshop some Capertons on that guy?
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you’d be surprised where you can find stylish overnight bags… the one pictured is customized by a member of our design team – sometimes it’s as simple as taking a cool canvas duffel and sewing on some vintage ski resort patches… other times you just pay to play and go with a higher end version – Orvis, LV, Patagonia – there are a bunch of great options out there. The more unusual, the better!
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Hipster Zipsters and Rugby shirts? Played out. The best travel advice I’ve ever read, and which you’ve echoed here, is to pack a navy blue cashmere sweater. It works with virtually anything, looks good dressed up or down, will keep you warm in the evenings, and will never go out of style. I buy a new one every year and take it on every trip, every time.
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