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The Authentic Gentleman’s Guide to Perfect Holiday Packing

Pack smarter, not harder.

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This month, our friends at InsideHook are launching a once-weekly travel newsletter. What it won’t include: longwinded diaries about backpacking through third-world countries and people “finding themselves.” What it will include: actionable advice on new and intriguing destinations around the world, along with hacks, tips and tricks to help you jetset more intelligently. Sign up for free (and a chance to win a $500 Mastercard travel card) here.

Regardless of where you’re headed this holiday season, be sure to mind the three following principles of packing:

1. Versatility
2. Comfort
3. And weight (or rather, lack thereof)

In other words, the perfectly packed bag contains an ecosystem of items that serve multiple functions, play well together and easily withstand the rigors of the road.

Below, we’ve pared it down to the 13 most necessary ingredients, from wrinkle-proof suits to odor-resistant undies to the two pairs of shoes that’ll suffice for any situation this side of a black-tie dinner. Plus: a couple of alternates per category for your more specific use cases.

Safe travels.

Your Bag: Away Solstice

After a year of using one nonstop, your correspondent can safely say that Away’s “Bigger Carry-On” is the best suitcase he has ever, er, carried on. Holds enough gear for even a semi-extended trip (yet fits neatly in the overhead), is durable as hell, and its internal phone charger has saved my cellular bacon more times than I can count (no more scrounging for airport wall outlets). Their new limited-edition “Aurora” colorway is a Borealis-inspired iridescent green, which not only looks cool but also should make it very difficult to confuse your bag with the next guy’s.

For Transporting a Suit: Bennett Winch 2-in-1 Canvas Holdall

For Guys Who Hate Wheels: Baboon Go Bag

Your Dopp: Gravel Expeditioner

As our intrepid managing editor referred to it, “OCD heaven in a dopp kit.” Gravel’s Expeditioner (also referred to as the Explorer Plus, don’t let their site confuse you) contains a neat grid of varying pocket sizes to accommodate all your gear in an organized (and mercifully segregated) fashion, plus a quick-access clear TSA pouch and a fleece-lined pocket for passport, cords, etc. Bonus: the whole damn thing is waterproof.

For Quick Trips: Gravel Explorer Slim Dopp

For Showing Off: Hard Graft Refresh Dopp

(InsideHook)

Your Tees/Socks/Undies: Unbound Merino

So here’s the thing about merino wool: not only is it super comfy, wrinkle-resistant and temperature-regulating, but you can wear it again and again and again and again and it just … doesn’t stink. It’s like some kind of weird fabric black magic, and it is key for your undergarments when traveling. Do you need to go full native and rock the same getup for 46 straight days ala Unbound Merino’s founder? No. But it’s kind of cool to know that you could.

For Gym-to-Boardroom Performance (Undie): Rhone Boxer Brief

For Gym-to-Boardroom Performance (Tee): Mack Weldon Pima Cotton Crew

Your Pants: Rhone Commuter City Pant

Hard to beat a good pair of lightweight chinos for versatility/packability — when done right, the same pair you had on with your shirt and tie earlier in the day can be cuffed and rocked with a tee and sneakers later on. Rhone nailed not only the cut on the Commuter City, but also key details like quick-drying Japanese stretch fabric, zippered pockets for both your wallet and phone and reflective trims for your nocturnal excursions.

For Decidedly Chillier Climes: Gap Flannel-Lined Flex Khakis

For Your Holiday Trip: Zanerobe Tartan Unblockshot Chino

Your Dress Shoes: Fliteless Counsellor Longwing Lug Sole

First, a shoe nerd tutorial: “longwing” refers to a style of brogue featuring wingtip perforations that run the length of the shoe — a longer wingtip, if you will. This pair from new concern Fliteless has got you covered on multiple fronts: first, their revolutionary design fuses the best of running shoe and dress shoe technology for minimum weight and maximum comfort (we’ve tried them, it’s crazy). Second, a classic brown brogue like this will play with everything from a proper suit to jeans and a sweater (see above). Third, the lug sole can handle any inclement weather you may encounter. Win win win.

For Boots You Can Chase a Train In: Wolf & Shepherd Chelsea Blitz

For Suspiciously Casual Business Trips: Sabahs