How to Pack for Vacation

The Directrice presents: How to Pack for Vacation.
Perhaps some of you are thinking, Thanks for nothing, Directrice. I took my vacation in July.
Please don’t be mad. Perhaps this advice will be useful next year. Or, perhaps you won’t find it useful at all, and therefore can’t be mad that it’s late.
The Photographer and I are on vacation and looking over what I packed, I am thinking I did a pretty good job. Guess where we are? The person who comes closest to the spot will win a Directrice coffee mug.

Maybe I don’t even need to say this, but the chief objectives in packing for vacation are (1) to pack as little as possible but (2) still have enough clothing to put on something stylish and clean (relatively clean) every day. Do we agree?
Did you think the objective was something else?
We agree about the objectives, right?
We agree about the objectives, right?

White denim jeans, striped t-shirt, navy cotton jacket
White denim jeans, striped t-shirt, navy cotton jacket, and primary shoes: black sandals
What is most likely to prevent you from achieving this objective?
Shoes. Cut this off at the pass. You are packing two pairs of shoes (one of which are black flats, unless it is summer, in which case they are black sandals) and you will wear a pair of stylish sneakers on the plane.

What else is likely to cause you headaches? Specialty underwear — e.g., Y-back bra, specially-colored underpants that won’t show through a particular dress, etc. If possible, try not to pack garments that require special foundations.
On to clothes!
But first: Do you have any special wardrobe needs for your trip? Are you attending a fancy dinner? Giving a talk? Going on an extended hike? If so, pack what you need for those activities first. Perhaps those clothes can be worked into the rest of the vacation rotation, but probably not.
Now on to general wardrobe, suitable for light physical activity: sight-seeing, museums, restaurants.
When I said, “as little as possible” I meant as much as you can fit in a suitcase and lift without difficulty. You do not have to lift the bag over your shoulder, because you are going to check it, but you should be able to maneuver it around the airport and manage it on a train, where you can’t check it. To give you some sense of capacity, my suitcase is a standard Tumi that fits in an overhead compartment, but can be expanded by 3 inches (after which it no longer fits in an overhead compartment). For a two week trip, I use all of that space.

White denim again, this time with a red linen top and khaki jacket + scarf and black sandals
White denim again, this time with a red linen top and khaki jacket + scarf and black sandals

Not wearing this "again" in this photo . . . this is just later in the day
Not wearing this jacket “again” in this photo . . . it’s just later in the day; this photograph provides another clue
Two weeks means you will need to wear everything in your suitcase three times — although there is some variation for tops (which I would wear fewer times) and jackets (which I would wear more times). But let’s start where I typically do — with pants. You will need 5 pairs of pants.
Pack 1 white or light colored pair, 1 medium khaki pair, 1 dark pair, and 1 pair of jeans. Wear the other pair of jeans.

Next, three little jackets: 1 black or navy, 1 light colored (white/ivory/tan) and 1 in any color of your choosing (including a white/ivory/tan alternate). You will probably wear one of these on the plane unless you decide to wear a sweater.
But here, I am wearing my navy cotton jacket again, this time with light colored khakis and sneakers
But here, I am wearing my navy cotton jacket again, this time with light colored khakis, a chambray top, a sweater, and sneakers; this photo provides more clues

Another clue
Another clue
Under the jackets, an assortment of tops: 4 striped tee shirts and 4 blouses.
Hint: Every top should go with at least 2 pairs of pants and 2 of the jackets.

For weather extremes . . . which includes airplanes, pack one sweater (black or navy blue) and two or three lightweight scarves.
The third jacket: white cotton, worn with a white linen tank and fatigue green pants
The third jacket: white cotton, worn with a white linen tank and fatigue green pants; a very good clue behind me

A clue for the art history majors
The final clue; this one’s for the art history majors
Now that you’ve picked out your clothes, you can select your second pair of shoes: sometimes I take a pair of black penny loafers, sometimes my leopard Mary-Janes. On this particular trip (a summer trip to as yet undisclosed location), I packed a second pair of sandals.

New sun hat, obtained while on vacation
The Photographer, me, and one new sun hat; The Photographer also bought a sun hat, but he felt that it was too dorky to wear for a photo
Essentials and Incidentals: I do pack a zillion pairs of underpants (it’s nice not to bother with laundry on a trip) plus a sunhat and 2 pairs of sunglasses.
Here, a confession: I packed three sunhats for this trip. And then I bought two more, although one will probably be a gift. They are all foldable and crushable, so they aren’t taking up much room in my suitcase, but I could have done better.

Have a fantastic weekend!

26 thoughts on “How to Pack for Vacation”

  1. Recently, I vacationed in Prague for 5 nights. My suitcase – a regular sized backpack! It was fantastic. I had plenty of options and didn’t have to wait for checked luggage. Less is definitely more.

    • That is very impressive. Very impressive, Susan. A heavy bag can sort of spoil a trip — certainly if there is much moving from place to place.

    • You are correct, Deborah! We are staying in Rockport, and the pictures are from Rockland (Farnsworth Museum) and Camden. Please send your street address to me at and I will ship your mug in the next few weeks!

  2. Darn, Deborah got it before I could. Rockland, Maine. Hope you enjoyed your lobster roll! Love the packing tips. The love of my life and I also travel light. It’s nice to be nimble when on vacation.

  3. I AM an art history major. Do I get points for recognizing Andrew Wyeth’s house?
    Glad to see you and your husband taking a nice break. Thanks for posting even though you are on vacation. I like your new sunhat.

    • You do get points, Nicky — it’s Christina Olson’s house and the background for Andrew Wyeth’s Christina’s World. We visited the site and had the best tour guide who was not just knowledgeable, but a great storyteller. If you send me your street address (, I’ll send you a coffee mug, too!

  4. It’s lovely to see happy photos of the Directrice and Photographer on vacation! Such wise advice to start with gear or special wardrobe needs, I will keep this in mind. Someday it would be nice to see the Directrice’s tips for packing for business travel.

  5. Principals like the two-shoe and wear everything three times are great vacation packing advice. Shoes are so bulky and take up so much room! I have shirked on packing enough wearables on occasion to leave room in my suitcase for anything I might buy, unless of course my H is coming with, because that’s what his suitcase is for 🙂

    • I thought I would get more push-back on the wearing three times, or the shoes, not white pants. White pants = summer. If stained, can be bleached after vacation. But you will note there are other options. So far, I have eaten an overstuffed lobster roll, an extra thick chocolate frappe, and too much fudge in the pants and no stains yet.

  6. Maine looks beautiful!! I love that house. What is that flaky layered pie type food on Directrice’s plate please? Looks delicious. I’m in/from Australia and have never been to Maine, and I have no idea what the food you’re about to enjoy is. My guess, if it’s a clue as your say, is a lobster pastry? Happy holidays! Ps your sun hat is perfect.

    • Justine — it’s a lobster roll! That’s a white bread roll, split, toasted, and often buttered, filled with lobster salad (lobster, mayo, a little celery). Heaven on earth!

  7. Yep, Maine. It’s pretty amazing when a state is so instantly recognizable!

    Nice to see a photo of the photographer. You both look great!

  8. Great advice and such perfect timing. I’m headed to Spain for two weeks and have been wondering about my wardrobe packing strategy. Thank you – your post has given me one less item to worry about!

    • Have a fantastic trip, Monica! So many wonderful spots to see, so much fantastic art, design, and style. My favorites (to date) are Barcelona and Bilbao, so hopefully one or both are part of your itinerary.

  9. Awwwww! I have a very deep connection with the Wyeth family (all 3 generations of painters) – I’m so in love with the Brandywine River Museum in PA as well. I even gave my oldest daughter their name! (well… her middle name). Andrew happens to be my personal favorite 🙂 Excellent vacation choice!

  10. My packing approach is similar but different in the details, for two weeks I would propably take 2 trousers and one pair of shorts ( or the other way around, depending on the expected weather), one skirt and one dress. I agree on the shoes though – two practical and comfortable shoes that work well with all the bottoms. These should be chosen first. With the tops I’m usually not as disciplined and take more than I need, but that’s not as bad, as they don’t take that much space.
    As a European I’m impressed that your fellow US citizens have regognized Maine – I don’t find this landscape very recognizable . But then again the only references I have are the books of John Irving, so nothing visual to go by.

    • Hello Sonja — I think the tell-tale signs were the lobster traps and the lobster roll (cold, cold water crustaceans, specialty of Maine) and the house, which is pure New England. But there is something about New England coastal cities . . . the architecture, the paint colors, the light. I associate Mr. Irving more with New Hampshire (where I grew up) than Maine (although Cider House Rules takes place in Maine); my father went to high school with him. My personal favorite is A Prayer for Owen Meany.

      • Ah, I see. And you are right about Irving, I remember now that there is actually a novel called The Hotel New Hampshire. I think A Prayer for Owen Meany was the first one I read. And it always impresses me when Americans say, “Oh, yes, I went to University with so-and-so”, because all these people seem so far away, but then again obviously the same happens here with local celebrities. 🙂

  11. To be clear: I love white pants in summer! I just can’t keep the darn things clean. That’s why I wouldn’t take them with me on vacation. Because I am a slob, they wouldn’t last a minute before they were covered in some local delicacy! But for the tidier eater, the Directrice’s advice makes perfect sense (as ever).


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