How to pack for a week away in a carry-on suitcase

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One weird way I think addiction plays out in getting dressed is to the extent that a person could get addicted to the feeling of nailing an outfit. I think any one of us could probably get addicted to any behavior that releases a rush of dopamine if we don’t pay attention to what happens after the fact but in the example of getting dressed, I wonder: do you ever get that feeling when you put something on and think, I nailed it, only to release the rush that then makes your head go, keep nailing it, or in other words: get! more! rush!

So you decide that this means put more outfits together, keep putting new outfits together that make you feel like you nailed it when probably, a more sustainable next step is just to wear the outfit, and if it all goes well, to maybe keep wearing it until your next good idea.

Clothes peak when they play best supporting role, but flounder as the main event. I find myself coming back to this thought a lot lately. I bring all of this up only because the thing about packing a good suitcase is, basically, nailing one good outfit and expanding it for the sum of your bag.

Here’s how to pack a carry-on for a week away.

Considerations

1. Where are you going (warm vacation, cold vacation, work trip)

2. Who will you be with (e.g. is this a family trip, are you going with friends who you like to share clothes with, is this travel that requires you make an important impression, like for work)

3. What’s the vibe of the destination (beach, mountain, city, and then within each of these categories: laid back, high intensity, fancy, etc)

Warm weather trips are easier to pack for because the clothes are light. For winter destinations, it’s a bit trickier because of coats and sweaters (I use my body as a second suitcase by wearing a ton of layers inflight) but in either case, these are the basic principles.

Things to watch out for:

Packing while overwhelmed.

• If you have kids, pack right after they’ve gone to school/camp but before you have started your own day, or after they’ve gone to bed. Really just during a window of time when time actually feels like it is yours

• If you’re a nervous flier, pack like 2 days before you leave. Be dramatic! Schedule it!

• Also, abstain from reading the news (if you’re nervous, I mean)

• And maybe stay off Instagram too, unless you are successful in using it for outfit inspiration that helps you wield your own closet, as opposed to think its a loser with nothing in it

• If your closet is not organized in such a way that makes packing seem easy (e.g. t-shirts are all together, shorts are in one area, skirts in another, etc) take everything out that you think you want to take on your trip, lay it across your bed and then edit/ultimately pack from that spread

Packing while under the influence.

• Of alcohol or drugs, sure but also:

  • Of who you’re traveling with/where you’re going. I find that when I travel with friends or am going somewhere that maintains its own specific brand identity (e.g. music festival), I start packing into shoulds. Like what should I look like in this place instead of what do I, Leandra the human, want to wear. Maybe this is specific to me, but I will never forget the first time I traveled to Europe for fashion week and brought a suitcase bigger than my closet, which was full of stuff I didn’t wear. This one particular red satin skirt sticks out in my memory as having been a bitch to pack, a perfect companion for synagogue but absolutely useless that week. What was I thinking?

    That I wanted to impress my peers, probably. In the end, you know what they say, your peers don’t care, and thank God for that.

Process

1. Make a list

   1. Start with how many days you’re going to be away

2. Reconcile how many outfits you’ll need (e.g. if it’s 6 nights away and your days are broken up by day look and night look, you need 12 outfits. This doesn’t mean 12 unique looks but 12 times to cover your body over the 6 days)

3. Start making the outfits.

Making the outfits

• Start with one category, like “beachwear” if you’re going somewhere warm. “Meetings clothes” if it’s a work trip. “Daytime touring” (khaki bermuda shorts!) if it’s a trip to a city. I’m using a warm trip as the example for this post, so starting with bathing suits.

Settle on taking no more than 3-4 suits and make the day outfits around them. Shorts (these are fun!), sarongs, and button-down shirts (I think this is probably the best one). Separates make it easier to mix and match. You’ll probably come up with a few of your outfit heroes here.

Identifying the outfit heroes

Pick 3 trip heroes and try to build a few outfits around them so as to limit the number of garments you’re taking. The heroes of the trip are the most versatile pieces you have with you. Figure a black one-piece bathing suit, for example. You can wear it to work out (hike?) all week if you plan to do that (ambitious), then turn it into a top at night — maybe with white pants like these (or these) or shorts, with a shirt-as-jacket over a la:

or you can pair w a skirt, a non-sheer version of which would be great with a bikini top and button down shirt-as-jacket for the same purpose too.

Khaite at left, Prada at right

And because the hero items are ~basics~, you can wear them several times with different bottoms (e.g. during day: a sarong, pair of shorts, ya di ya).

How to figure out what your heroes are

Ask yourself: what from the day can I integrate into the night?

You’ve already seen the example of the black b-suit, but can any of your sarongs also make for, say, scarf tops (or even skirts) at night?

Are there any shirts you’d pair with a fancier skirt, or shorts for the night? (Figure a button-down like this one, maybe a tank top.)

A more tropical and formal way to way a lace tank at left, or the walking-tour way at right. Good over a bathing suit too:

Any day dresses that would look cool with more formal shoes too?

Build 3-4 outfits around these versatile pieces and then fill out however many other outfits you need with the garments not yet accounted for.

Some ideas if you can’t think of any heroes:

• Denim or cotton (soft or poplin) or cycling shorts

• Neutral-color button-down (white, brown, navy, black, ivory all good)

• Silk scarf/sarong

• A beach dress (top?) with personality

Now, after your trip heroes are picked, my rule is: NO THROAT CLEARERS

Your wardrobe heroes are the security blanket garments that make you feel most prepared to travel/confident to get dressed and look like yourself (meaning: good). A throat clearer is kind of like the equivalent of this security blanket, but past its shelf life. Like imagine yourself with your baby blanket on the subway at 17 years old (not saying this was never me). The low-risk clothes are already packed, so here with the fillers around the heroes, we go balls to the walls

with wrap-over things like this, or top things like this or this.

The basic necessities

Now you pack underwear and bras. You do this so late in the game because you’ll want to base this on the outfits you have packed. Do certain garments need special undergarments?

If there is any jewelry you want to bring for certain outfits, pack that now too. And your toiletries/makeup.

Finally: shoes

Not my strongest packing suit. I usually over-index but you could probably get away w one day pair and one night pair. Or one day one night and one that could be worn to both. Good example of a shoe that could be worn at both day and night:

Salt water sandals, Gabriela Hearst boat shoes

How do I mean? Well, consider either of them with a dress like this or this (maybe a sarong and button-down is a better example?) for the days, or a dress like this for the night.

But then, also, rawr what could happen if you wore the day dress again at night with a slightly oversize white shirt-as-a-jacket (as you can see, this is a theme — the slightly oversize button down shirt is, no q, a suitcase/general outfit hero) and a pair of heels? You could even tuck the dress into some shorts if you’d rather not show your legs.

Next: try the clothes on

It takes time, but it’s worth it.

The Plane outfit

Comfortable bottom (sweatpants work but for a summer trip, I like a pair of white jeans — just in case you’ll want them there); lightweight sweater (or sweatshirt) you could wear while away, another versatile garment under, like a white t-shirt, plus silk scarf around neck to later be fashioned into sarong and shoes you could wear too while there too.

And then that’s it — you’re packed.

But wait, your travel bag

It doubles as a beach bag, so maybe it’s straw, maybe it’s a material like this or this.

Toiletries go in a pouch (is this a deal when you consider it as a evening bag or am I crazy) in the bag that you can reuse as an evening clutch (like this one from Man Repeller’s first product drop), you bring your computer if you have to work and if the toiletry bag idea is too scrappy, add in one evening bag, preferably a soft one (?) so it packs in easy. I usually keep jewelry in here too.

Pearls are good for a summer trip — they wear easy on the beach, can be submerged. inwater, and will 10/10 fancy you up if you wear them out at night.

And now you’re really packed. That’s it. That’s all. God speed and have a safe slight.

Signing off,

Leandra