Classics: The Well Dressed Traveller’s Packing List

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Travelling can turn even the sharpest minds into puddles of dumb.  Especially if you’re hitting multiple locations and/or flying overseas.  You want your clothing options on the road to be sharp, yet foolproof.  Don’t pack with the mindset that you’ll need to assemble an outfit for each day.  Instead, pick one group of complimentary colors, and assemble items around that palate which you can mix and match with each other.  What you sacrifice in variety you more than make up in simplicity and versatility.   Here’s three colors that most if not all men look great in:

  • Navy
  • White
  • Grey

The scenario below shows a longer trip.  Specifically a week and a half with an early stop in the states for a wedding, then afterward heading overseas for a week in London.  If your trip is shorter, say a long weekend, cut out bulk by eliminating a few dressed down items.  More on why later.

Dressed Up:

The Why:  For the suit, worsted wool will work better with jeans than a solid/flat fabric because the alternating black with white or light grey threads adds some depth.   That depth helps make it look less like a suit jacket and more like a sportcoat (tweed sportcoats = lots of depth) when worn with jeans.  The light grey will also give it some contrast when worn with your denim.  Both pairs of shoes work well with suits, but aren’t too fancy to wear with, again, jeans.  Don’t be too concerned with mixing up your shirt arsenal.  The sunglasses can be worn with just about anything.

 Dressed Down:

  • Navy Cotton Sportcoat: GAP (out of stock)
  • White OCBD and Black Gingham Shirt: Bonobos, Nordstrom
  • A couple of favorite t-shirts: Thrift Store, Target
  • Lightweight Navy and Grey V-Neck Sweaters: Banana Republic, J. Crew Factory
  • Dark denim and grey 5-pocket pants: Levi’s, Hickey Freeman (out of stock)
  • Grey Suede Desert Boots: Jackthreads (out of stock)

The Why:  A cotton sportcoat is perfect for travelling.  Jackets have pockets.  You need to carry stuff when on the road.  A jacket is a slim way to keep things on you without overloading your pants or necessitating a bag.  Cotton means it’ll breathe, go well with jeans, and can handle a decent beating.  Bring two dressed down shirts for under the sweaters/blazer (the dress shirts can obviously be worn here too), and meanwhile, the bold check will look smart with your suit as well.  Go dark with your denim.  Bring your jeans that are well worn but still free of rips/tears.  Now’s not the time to break in your raw stuff.  The grey 5-pockets are optional, but great for mixing it up and creating a not too dressed up combo of the blazer with a grey cotton bottom.

The Little Stuff

The Why:  If the forecast calls for lots of rain at your destination, pack a small umbrella.  If not, buy one there if needed.  Brown/Black strap watches to match your shoes, and the less weighty option would be just one watch with a clean stainless steel band.  Card case instead of a wallet because you’ll be on your butt for too long while in the air.  About the belts… that grey suit doesn’t have loops, but instead it has side tabs.  The belts are to be worn casually of course, but you could easily bring a reversible dress belt with a matte buckle and use that to hold up your jeans and suit pants.  Make sure to keep your magnetic stuff away from your laptop, iPod, phone, and wallet.  You don’t want to risk screwing up any data with your wurkin’ stiffs buttons, especially if there’s a screaming toddler on your plane and you desperately need your tiny iPod to drown out the noise.

The Big Stuff

The Why:  Garment bag engineering has come a LONG way.  There’s now so many pockets, snaps, and elastic inside of these things, that your clothes are almost pulled into order by some magic luggage tractor beam.  Wire hangers are a huge no at home, but use em’ here.  Stick with a midweight trench and layer underneath if it’s cold.  Wool overcoats are bulky and heavy.  If you won’t be wearing it on the plane, hang it inside the bag on the same hanger as your cotton blazer and jeans.  Those should be on one of those lightweight suit jacket/pants hangers you get with your dry cleaning.  Layering multiple jackets on one hanger saves lots of space.  And bring the detachable shoulder strap for the brief.  If you’re stuck lugging the garment bag up steps (lookin’ at you London Underground), you’ll want to go hands free.

Final Notes:
  • Wear your suit on the plane:  Besides getting treated better, if the airline does happen to lose your luggage, you’re prepared.  Better to be overdressed and say: “They lost my luggage” than to be wearing pajama pants and a t-shirt to a wedding or big meeting, only to say: “they lost my luggage.”  Go casual on the way back.
  • Cut bulk by eliminating casual stuff:  Err on the side of dressed up if you’re travelling light.  It’s much easier to take something more formal (like a suit jacket) and dress it down (wear it with jeans) than to try to dress up something super casual.
  • Check a bag.  Really:  Free thyself from your luggage anchor!  Walking around a nice airport with nothing but a briefcase is a terrific feeling.  Yes you risk them losing your luggage.  But it can be well worth the risk.  And if you’re in that “I might be able to get away with a duffle” range, consider sizing up.
  • Conserve space inside:  Use your shoes as compartments for small stuff.  Your watch, belts, socks/underwear, etc… can all be shoved in those.
  • Use newspaper as shoe trees: Not as good as the real thing, but it will help them keep their shape and absorb moisture.
  • Use the hotel laundry bag for your dirty stuff: It’s just a plastic bag inside the closet.  Use it to keep your dirty stuff from taking over your room and later on your bag.
  • Pack lots of socks & underwear:  You’re only as comfortable as your feet and crotch.  A clean pair of socks and underwear can work wonders.  If you’re the groin & foot commando type, well… good for you.
  • TRY to have fun:  Treat yourself to a beer on the plane.  Download some podcasts you’ve been meaning to get to.  Smile at the flight attendants.  Travelling used to be glamorous, and it still can be fun if you go in expecting good things.  Yes, it doesn’t shake down like that all the time, but here’s to hoping that your next trip does.