I’ve packed plenty of times this summer.

My wife and I traveled for two weeks, each with only one carry-on. We went from San Francisco to Miami, Indiana, Chicago (for a day), Washington D.C., and finally ended up in New York.

We experienced a bunch of different climate combinations and weather changes: sunny and humid, wet and rainy, warm and overcast.

Currently, in New York, we’re in the middle of a seasonal shift, from summer to fall.

And yes, up until recently, we were living out of the same carry-ons we started with two months ago.

Living lean, traveling lean

Packing for versatility and flexibility is always a smart move, whether you’re going away for the weekend, or traveling for weeks.

What’s the best way to do that?

Here are a few things I’ve learned over the years, that I was able to put into practice this past summer.

Evaluate your situation, travel plans, and destination

Asking yourself the following questions will help you put your trip into perspective. It’s important to be honest with yourself so you’re not overpacking (or underpacking).

What activities do you have planned? Will you be on your feet a lot, or are you just lounging around sipping Mai Tais?

Is this a business trip, or is it for pleasure?

Any idea what the weather and climate is like at your destination this time of year? The average high and low temperatures? Humidity percentage?

Where are you staying? Can you do laundry if necessary?

Lay it all out

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Here’s a strategy I’ve always used: lay out every single item on your bed or floor. Seeing everything laid out helps you visualize how things will go together.

If you’ve been following the Lean Wardrobe philosophy, most of your clothes will complement one another, but laying everything out is still a good exercise.

Footwear, FTW

After knocking off points 1 and 2, you’ll want to take into consideration your choice of footwear.

Shoes are super important, not only for aesthetics, but for comfort as well. If you’ll be doing a lot of walking or hiking at your destination, your shoe choices will be very different than if you were going on a short business trip.

It gets a little more complicated in situations like what I just experienced, where I spent part of my time lounging, vacationing, and beaching, and the other part in a big metropolitan city. Two completely different situations called for two different sets of clothing, but in the interest of packing lightly, I just had to make it work.

In case you’re curious, I took a pair of white Chuck Taylor converse sneakers, a pair of tan boat shoes (similar), and a pair of cognac-colored leather loafers.

Don’t forget the little things

Underwear? Toothbrush? Socks?

Sometimes I get caught up making sure my clothes work well together that I forget to pack these items until the last minute.

Keep a checklist if possible, and mark everything off as you go.

Your hotel (if you’re staying in one) usually has the necessities, such as a hairdryer, shampoo, soap, Q-tips, etc., so no need to bring those things. You could also hit up a local convenience store at your destination to stock up on those necessities so you don’t have to travel with them.

Strike a balance

It’s easy to overpack for the sake of having options. I’ve done this many, many times, always with the same result: I don’t use half the options I pack.

It’s good to throw in an extra shirt just in case, but three extra shirts and two extra pairs of pants for a short weekend excursion is probably overkill.

By the way, this is why having an interchangeable wardrobe is so helpful. You can grab any shirt from your closet and you’re guaranteed a good pairing with your pants, shoes, and jacket, every time.


Here are a few extras that are worth your time if you really want to nail this Lean Packing / Lean Wardrobe thing.

1.) My friend Antonio over at Real Men Real Style covers topics like building an interchangeable (i.e. Lean) wardrobe and having the right wardrobe when traveling. Here’s the article via The Art of Manliness.

2.) Here’s the video about putting together your interchangeable business wardrobe while traveling.

(Can’t see the video? Click here.)

3.) The last video is a series from Mr. Porter, which I’ve included just for fun, so you can see how other stylish men pack their suitcases.

(Can’t see the video? Click here.)

I’d love to hear your packing tips, tricks, and routines! Leave em in the comments below.


Top photo via Emiliano

If you found this article useful, make sure to check out our Lean Wardrobe resources page.


7 Responses

  1. Linus on

    Thank you for your post and ideas! Here is what I had with me for a 4-day business trip that included a lot of time on my own. I chose to spend it outdoors at a few forests and environment conservation areas nearby. This is reflected in my packing.

    Here is my list: http://himmelochstoft.blogspot.fi/2013/10/carry-on-packing.html

    – Flyye Fast Pack EDC pack, ca 30 litres- HSGI T.E.A. Bag as a EDC bag on the conference
    – Camera, Fujifilm x-e1 + Xf 35mm, spare battery
    – Sleeping bag, Halti + liner + pillow
    – Haglöfs stuff vest
    – 2 shirts, 2 pants, 1 sweater, underhirts, boxers, socks, woolen socks, tie
    – Fjällräven G1000 coat + Mac in a sac raincoat
    – 1 pair Brown derby shoes + galoshes
    – hat, necktube, gloves, cap
    – pocket towel, wash kit
    – iPad + keypad + charger, phone + charger, headset
    – pens, flashlight, passport, wallet
    – packing pouches

  2. Nathan on

    If you haven’t already seen OneBag.com, you need to go check it out. Doug Dyment has it all figured out (well, most). He suggests clothing that might not appeal exactly to EG readers in general, but you can always adapt your personal style into the system of the one bag.

  3. Shailesh on

    I travel for 2 weeks at a time quite often and usually don’t check a bag. The biggest challenge is having a work wardrobe and weekend wardrobe for those 2 weeks.Here’s what i pack:

    2 twill white shirts
    1 blue twill shirt
    1 pink twill shirt
    2 dress slacks (charcoal and light grey)

    1 white OCBD
    1 blue OCBD
    1 pink OCBD
    1 pair of chinos
    1 pair of dark jeans
    1 pair of sneakers
    1 pair of gym shorts

    Dopp kit
    underwear for 12 days
    undershirts/t-shirts for 5 days

    Then i fly wearing my suit, one other dress shirt, and a pair of bluchers. It all fits in a carry-on and i have everything i need for just about any scenario.

    • Barron on

      yep! that sounds perfect, and pretty much everything in there goes with each other. On top of that, they’re basic colors that won’t draw too much attention if you have to wear them more than once.

  4. NF on

    I’ve always struggled with how to travel with or pack a suit or sports coat when I didnt want to wear it on the plane. any recommendations?