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You Need This... I Promise

The Packing Groove

what i was supposed to wear on Saturday night

It really feels like "going somewhere" is in the air. Personally I have loved the year-long pause on travel… I didn't realize how frenetic so much of my life was until it stopped so abruptly. I actually liked it. But let me tell you, based this past weekend, the thing I really need now (I promise) is to get my travel groove back. Sid and I went to Greenwich for 36 hours this past weekend for a retirement party for a dear, dear friend. And when it came to packing, I would give myself about a C-minus. It ended up okay, but I spent waaaaayyyy too much time on it. Maybe you are as out of practice as I am, maybe not, but I will share all the ways I blew it and refresh myself on all the things I know to be true when it comes to packing.

First of all, even though I had a full weather report, and a clearly outlined social schedule, I was paralyzed by what to bring to wear. We had to leave for the airport at 8am on Saturday morning, and I went to bed on Friday with my bag only half packed. I just couldn't get it together. In the past, I have packed for a two-week trip to Europe without even thinking about it, but this time, I felt like a pro athlete psyching myself out. Performance anxiety.

We were scheduled for a casual dinner party on Saturday night, but the forecast showed 68 degrees and this threw me for a loop. A sundress and a wrap would have been a layup, but I know myself, and when my feet are cold, my whole body is cold… so sandals were out. None of this would matter, because what I actually ended up in on Saturday night was the exact same thing I left the house in at 8am that morning. (I did not plan it this way, but more on that later.) Dressing for the plane is maybe one of the most important things for me – I want to be comfortable and chic (who doesn't?) and often I will plan on wearing those things again. This time I wore white flared jeans, a tan safari shirt, and short brown cowboy boots. These are my default travel boots – I find that it's not just the plane that can be freezing, but airports are almost always extremely well air-conditioned. As bad as it is to be delayed at the airport, it's worse to be delayed and cold at the airport. And these can be year-round boots… cowboys wear them in the scorching heat, don't they? To me they are seasonless.

Although I didn't get to wear it, the outfit I had planned for Saturday night would have been great. Straight-leg jeans (I have worn wide-legs to death lately and needed a break) and this striped Grace Top with a cardigan over my shoulders. I brought this one, made with patterned silk, thinking it could be both a sweater AND a scarf when worn around the neck. The pattern mixed with the stripe felt kind of kicky and festive to me. The plan was to make a game-time decision on sandals or the boots I had flown in. BUT (isn't there often a "but" when you're traveling?) Sid and I got sidetracked while driving around Fairfield County to look at all three houses we had lived in years ago. We ended up getting stuck in traffic and ran out of time to go back and change before dinner.

Though I would have loved the change to take a quick shower and throw on a prettier, more festive shirt (the little smocking on the neckline is so special and feminine) it would have meant skipping that spur-of-the-moment detour down memory lane. It was a sweet little adventure and worth it to me. In our house we always say that who you eat with is more important than what you eat, and the same can be true here. The experience is always more important than how you are dressed to have the experience. Don't get me wrong – most of my career has rested on the idea that looking great can make you feel great. I believe that. But if that ship has sailed, let it go and lean into whatever you've got on. I had a great time at the party in my airplane outfit. And no one cared, or even noticed what I had on, because we were all laughing and smiling and chatting.

Saturday and Sunday, documented

Sunday posed less of a packing challenge. It was supposed to warm up a bit, so the Sunday church service didn't freak me out as much. (The retirement party was, in fact, our friend's final sermon – he has baptized and married a few of my girls, and outside of his religious duties, he is also a heck of a lot of fun.) I packed this black sundress and last year's black version of our hippie-ish buckle sandal, knowing we'd be outside on the grass. I brought along a plaid wool shawl, thinking of the lower temperature. I had a "summer in the Scottish highlands"-type getup in my head, but in fact, the wool ended up looking way too heavy by the time it warmed up. I should have gone for something thinner… lightweight cashmere is just as warm as a big fat cape, but it folds up much smaller when you aren't wearing it. Two people commented on the huge bundle of wool sticking out from my small bag. ("Wow.. you are prepared" from one; "you must get really cold" from the second.) It didn't bother me to hear – not everyone picks up on themed dressing – but again, I usually know better than this. I almost always have a thin cashmere scarf or cardigan in my bag (not packed in the suitcase) in case it gets cold en route.

So here's what I know… really groundbreaking stuff here:
Rule #1: When you are cold, you are miserable, no matter how good you look.
(I may have overdone it on this one with the wool cape in June.)
Rule #2: Don't let your outfit get in the way of having a good time.
It's just clothes.
Rule #3: Make a checklist.
Based on how this trip went, I will be doing this more formally from now on. I'm not sure where you are going next, but I will share my own checklist of the things that should always make it in my bag, no matter the season or destination or social schedule:

- Sunscreen. Sometimes at hotels they have prepackaged squares and I will nick a few extras to keep in my dopp kit… I never check a bag and almost all sunscreen bottles are too large to be carried on. On the trip before this one, I was in a hurry to get out the door, and squeezed some into an empty prescription bottle!
- Sunglasses. Sid and I nearly always forget these.
- ID. This sounds obvious, but truly Sid and I verbally confirm every single time because both of us, on separate occasions, have forgotten them at home before early-morning flights and had to get one of our daughters to drive out to the airport for a handoff. They loved that.
- Purse. Okay, this is really, really important because it will probably be in every photo you take. I love to bring both a small crossbody and a small bucket tote in addition to a larger tote bag and just stuff the littler ones inside when it's time to board.
- Bathing suit. You never know.
- Pretty pajamas. Even the worst hotel room is okay if you have a hot bath and a nice nightgown.
- Pareo or track shorts. Both solve the problem of "how do I get from the hotel room to the pool?" I don't know about you but I feel silly in the elevator in a robe. And they are both multitaskers. The pareo can act as a skirt, and I can take a run in the track shorts.
- Boyfriend Shirt. Makes an bonus outfit with the pareo, or a pool cover-up.
- Hair hooks. I bring two.
- Tees. Very Jackie O in Greece with white jeans.
- Scarf. Takes up hardly any space but gives a lot of style.
- Cardigan. See Rule #1.
- Running shoes. I love to get in a run wherever I am… it's a nice way to get a feel for a city.

Good luck. Hope you get to go someplace fun sometime soon.

From Ann

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