How to break every packing rule anyone has ever told you to follow and have it still turn out great
Sometimes packing is just about a vibe & a you don't need to have a glamorous vacation to have great outfits that make you happy!
We are back from a week at my in laws cottage in Door County on Lake Michigan. (No comment on the fact that re-entering reality has been insane and after about 2 days back at work the relaxation and chillness I felt from a week where my average screen time was under 30 minutes was erased! why is it always that way!??) It was a great week. A week where we move from kitchen table to beach to lunch on the deck to the raft to the kayak to boogie boarding to beach walks to board games in the living room to pizza and gin and tonics and endless games of cribbage and late night swims and beach bonfires and rinse and repeat.
Family vacations that involve sharing space with family can be wonderful, but are also not without complexity (the most diplomatic way I can think of to describe the situation) — but, three years into this annual trip with all three of our kids, and I feel like we have really honed in on how to make it work, what to expect, and how to all relax and enjoy time together and minimize TENSION. And, I can honestly say that we had a really lovely time. Door County is my husband’s happy place - he grew up spending his summer’s there. Before we got married, we lived in Madison and so we spent a lot of time at the cottage. And now, it’s a very special place to be able to go as a family. We spent a large part of the trip discussing how we might be able to spend more time there in the future (also not without complexity but I would love for my kids to get to experience more than a week there in the summer!)
Family vacations that involve moving 5 people via taxi/plane/rental car are also not without the complexity of getting all the stuff you need ready to go. This isn’t about getting my kids ready, or making sure all the stuff we need as a family (which, for the first time in MANY years, felt sort of minimal this year — our youngest is 2 and that sort of feels like the age at which the amount of stuff is starting to decrease and will continue to!) More about how I handle packing our whole family here. Instead, this about how I packed MYSELF.
If you asked me how to pack, or if I was helping you get ready for a trip, or giving you my best tips on how to pack a perfect suitcase for whatever trip you have on your calendar— I’d tell you the rules - you need less than you think, don’t overpack, make a list of what you’re doing everyday, pack outfits, try things on, stick to a color scheme, no more than 3 pairs of shoes, etc etc etc.
But what about those trips when you don’t have an itinerary for every single day? It’s not necessarily tropical or glamorous, but it’s relaxing and fun and happy and even though there may be no social agenda to speak of, or anything fancy or big or momentous on the calendar you still want to feel good and like yourself and get that perfect little boost that comes from wearing an outfit that makes you feel like your best self.
Right now, most of our summer trips fall into this category. There isn’t that much of an agenda. It’s not a huge adventure. There isn’t a plan for every single day (other than get to and from the closest body of water as soon as possible and make sure everyone eats meals at reasonable-ish times and something other than ice cream for all meals) — the days kind of run together and look pretty much the same. Probably, our summers for the next few years will look this way! Most of our trips, actually. I can’t wait for more glam vacations in the future, and I know we’ll have them, but for now, I’m so grateful for how we spend our time traveling.
So, I’m not packing for the most glamorous vacation circuit. For anyone in the South of France or Italy or Greece or southern Spain — I’m living vicariously through you — and soaking up and loving what you’re wearing. But in the meantime — sue me if I want to have a great outfit when I go to pick up pizza from the local shop, or sip a cocktail with a side of cheese curds and fries at a casual outdoor restaurant, or feel good when my one outing of the day is to pick up coffees and pastries at a local cafe. Or, maybe just feel chic AF when we drink gin and tonics on the deck while the kids run wild on the beach. A day-by-day list of activities and what I was going to wear to each of them wasn’t going to get me to the right outfits (or any outfit other than bathing suits + something to cover up with) — I needed to know how I wanted to feel when I did get dressed and put on real clothes.
So, how did I pack? I’ll start with what I didn’t do: I didn’t have a clear itinerary to make a list and prep for. I didn’t plan for and assign an outfit for each day. I didn’t force myself to follow a particular color scheme. I didn’t create a capsule of any kind. I didn’t follow any rules about how many tops and bottoms and shoes I needed and how many ways I would need to combine them all. I didn’t give myself a few days to edit and tinker and think (NO TIME FOR THAT!) I didn’t stick to things I could wear 2+ ways. I didn’t take my favorite pair of jeans out of my suitcase despite knowing in my gut I wouldn’t need them and they take up a decent amount of space (I did wear them but only so that I could prove to myself that I could wear them, not because they made any sense to wear!) But you know what — it worked out totally fine!
I loved what I wore. I had choices. I had something for everything we did. And, even though I definitely brought a few too many items, (jeans aside, I also somehow ended up with 4 white tank tops/tees which was unnecessary but was no big deal), I fit all my items in a suitcase that I shared with my kids, which, at the end of the day was the only rule for myself that I did follow!
Quick side note: let this be your reminder to make sure you put a tag on all your suitcases, we actually had someone take our big suitcase when we got back to Boston and THANKFULLY they had their name + contact info on their suitcase and we could easily make a switch - but we didn’t have a luggage tag on ours, so it could have been a big mess!) Also BTW that for our next big plan trip I am definitely upgrading our current big suitcase situation to this one — we have multiple carry on sizes (I’ve had mine for a decade I think!) and a medium size and it’s time to have a large one that is as sturdy and destruction-proof as the others.
What did I do? Let me recap for you:
I packed fast. We left Saturday morning. The day before I worked from home and used time in between meetings to move things I had pulled out into the valet hooks in my closet + fill in with other necessities and lay it all out on my bed so I could see it all together before I actually put things in my suitcase. I was packed by Friday afternoon. Having everything laid out helped me do a very quick and dirty validation that I could fit the stuff I pulled in the space I had, and also make sure that I had a somewhat sensical distribution of things (eg: not only bottoms, enough pjs, etc.)
I had a list in my notes app that I started the week the trip before to keep track of needs or anything I knew I didn’t want to forget. I always do this on trips — just helps declutter my brain a little bit and make sure that I don’t forget any essentials. I use it up until the moment we walk out the door — tracking things like making sure I throw my kindle in my bag, grab my airpods, any last minute toiletries, and even passports when needed.
I took fewer pjs and workout clothes than I was initially inclined to bring. I always bring too many of these things and I also knew I had access to do laundry whenever I needed to. This was a smart move!
I packed fewer dresses than I wanted to. This is a casual trip. I reminded myself that over and over again. I forced my pragmatic lenses on!! I was happy to have mostly pants, shirts, shorts and I wore them all a lot. I did wear the two dresses I brought and it was the perfect number!
I packed joyful stuff that I love to wear. I didn’t bring anything I’m lukewarm on. I ignored rules about practicality, or going together, or a “collection,” of things that would go together. I packed a new bright yellow tee that I wasn’t quite sure how I would wear but I had faith I would figure it out because I love it so much. When my outfits didn’t necessarily fit what I was doing, it didn’t matter, because I loved what I had packed and I wanted to wear it!
I remembered that, yes, on a day-to-day basis, when I’m adding things to my closet, there are rules that I follow to make sure I will wear the things that I buy and don’t have that feeling of, “a closet full of clothes but nothing to wear,” and I said “F you” to that rule for a week — not everything made sense, a lot of things were impractical. It was a lot of form and only a little function. I got to let go of practicality for a week, I didn’t worry too much about function - I wore all white to get and eat pizza, which I would probably not do IRL, but on vacation - why not! Because, after all, this IS SUPPOSED TO BE FUN!!!
And, reader, it was, after all, fun. Not to toot my own horn, but actually exactly to toot my own horn — I loved what I wore. I had fun getting dressed, I felt great in my clothes, I felt silly when I re-packed 4 white tops (especially since I never touched two of them!) but I definitely didn’t beat myself up about it. I felt great on vacation and it was fucking fun! And it didn’t take an exotic trip to Europe or somewhere tropical or sans kids to make it happen!
And so, I present to you…the outfits!
I got this athletic dress at the beginning of this summer on a bit of a whim, but it fits like a dream and so I kept it. I’ve been wearing it a ton - it’s the perfect thing to throw on in the morning and I like not wearing leggings. It was also perfect for a morning of hanging with friends and going out to lunch in Madison before we spent about 4 hours in the car. I wore it three times on the trip. A+ move. Not pictured here but I wore it with my Salomon XT-6s which I also wore on the plane and every morning for my beach walk. If the price tag of that dress makes you cringe (I get it!) then may I also recommend this great one from Old Navy.
Our first morning was a little chilly, so I opted for a lightweight sweater (which also doubled as my layer on the airplane, and over my shoulders in the evenings), and trusty white linen shorts. You can’t see, but I’m wearing a gingham blouse.
We really don’t do much while we are at the Lake, but one thing we do do is shlep to an insanely touristy restaurant so the kids can see the goats on the grass roof. So touristy that at 7:45 AM there was an hour+ wait for a table. We skipped the breakfast wait, got muffins and croissants instead, and watched the goats from the playground and beach across the street.
When I wrote that I wanted to have a cute outfit to wear to get pizza…I meant it. I wore this to place a takeout order for pizza and salads and then sit outside at a bar next door and order a pina colada and french fries while we waited for our dinner. Proof that I wear all white (anyone can wear all white!!) Also a great simple tank ($11!) with clean lines that I recommend to everyone! Also, if you’re counting, rewear count (of the pants in this case) = 1.
One thing you can count on in Wisconsin is that if you are going to have a wait at a restaurant, there is most likely a bar that will happily serve you a drink while you wait (even if your wait involves being outside or a walk away from the restaurant!) In this particular case, we waited over an hour for a seat at the “train restaurant” aka PC Junction, which has a counter bar area that is tended by a train that delivers drink, food + entertainment while you eat. Other attractions at the restaurant (for kids!) included go-cart bikes, baby chickens, swingsets, a play train, multiple slides, a giant chessboard and a big in a pen called “pigapalooza.” (The Midwest really is best!)
Told you I would find a way to make the yellow shell shirt work! I was influenced by an Instagram post earlier this summer and I loved this shirt, and after nearly 4 weeks in transit I finally got it! It’s big and oversized, but perfect to pair with bike shorts (or, as you see below, linen pants!) I’ll wear it with jeans too - just one of those pieces that makes you happy!
I found a way to wear the shirt again (Rewear = 2), along with black linen pants (these were my travel pants - in addition to wearing them multiple times during the week, I wore them on the plane ride in both directions! Not pictured but I’ll add 3 to my re-wear count for those, making it Rewear = 5).
A highlight of our week was attending the local 4th of July parade, and this is what I wore. I know I’ll wear this wrap skirt from Tuckernuck x Studio McGee a ton this summer! PS: the air-dry situation via this and this + drying in a braid was really doing it’s job on this trip!
For the evening of the 4th, we had a cookout with my husband’s cousin and her family, with a big beach bonfire and fireworks. They are just a few doors down the beach from us, so this is what we wore to walk over to their house! The white linen pants again (MVP?!), plus one new white tee appearance (we’ve seen 2 of 4 and only b/c I spilled on the tank I wore earlier in the day). Rewear = 6.
On our last night we had big plans to go to a new floating sauna on Lake Michigan that a friend of a friend told me about, and I had been looking forward to all week. Sadly, en route, a huge storm blew through, including lightening and a ton of rain and the sauna (on a boat) had to close up. We pivoted and went out to dinner at a cute restaurant in Bailey’s, and I wore this dress (not a great pic!) that I love! I’m devastated that I didn’t get to fit the sauna in this trip - but if you are in the area PLEASE GO!!!
If you made it to the end, thank you! And, if you like seeing what I’m actually wearing - I’d love to hear! I’ll be repeating these outfits all summer long on the weekends — it’s good to bring a little vacation back into your real life, and because these were outfits that made me feel legitimately good and happy. Even on a trip when most of the day is spent in a swim suit covered in sand and a UPF cover up of some kind, it makes me happy to put on an outfit, even if just for a little bit, that I love. And, honestly, I’m not sure what more of a reason I need than that!
ICYMI
From the Archives: To All the Vacations I’d Love to Go On
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I love this piece, Christina! It's so inspiring and helpful seeing how you rewear your clothes into so many unique outfits over the course of the week! So relatable! I'm excited to get dressed after reading this :)
pack what brings you all the joy! and the white wine supervision outfit is too real!! loved this piece