To all the vacations I'd love to go on
Specifically, the outfits I'd dream of wearing on each of them, and also: why does it take so long to get ready for trips??
I started writing this letter (note: at time of publication, I started this letter several weeks ago!! thanks for sticking around and bearing with me while I took an actual break for a bit!) from my local library, taking a break from doing endless errands and running up and down the stairs in our house to organize ourselves for our big trek to the Midwest. My in-laws spend their summers in Door County, and we go out there to spend time with them, plus tacked on a trip to Madison to visit friends (my husband and I used to live there!), and my husband even squeezed in a trip to Sand Valley). Thinking about getting ready for a trip always occupies a lot of time in the week or so leading up to it. And the reality is that the prep does always take a decent amount of work (and many last-minute amazon orders and errands run). But this time around, one thing I really noticed, is that in all the getting ready activities, the time it takes to do the preparation things (the things including, but not limited to: making sure we know/have what we need, doing laundry, packing clothes for my kids, packing myself, updating several shared notes with my husband to keep track of what we still need to add to our suitcases or amazon carts, making sure everything is all set for our house to be left uninhabited for an extended period of time, etc.) expands to fill the time I have available.
It’s funny how that happens. Funny isn’t the right word, actually. It’s annoying. As it happens, while I was preparing for the trip, I had A LOT of extra time, as I took several weeks off while I was in between jobs. (note: I started this week! If you follow me on instagram, you know my start was a little less than ideal since we were impacted by the IT outage and it took us several extra days to get home plus an extra super special 12+ hour stint in the Detroit Airport - good times!) More on the new job and the changes that come along with it at another time - it’s a big change, but a great new opportunity that I am both excited for and nervous about!
Because I wasn’t working (and my days were not nearly as full as they typically are), I noticed that the work of getting us ready to leave our house for the airport before we’re all normally awake and be away from home for almost two weeks took up as much time as I had available. Which was, basically, all my time. But, when I’m working, I somehow find a way to fit all the prep work into the time I have outside of work and other family things we have going on over the course of a given day. And sometimes a little in the early mornings and the evenings after all the kids have gone to sleep. This is truly not a novel realization - it’s something I’ve (almost) always known - and something I honestly experience at work - the things you have to do can expand to fill the time you have available. Sometimes this is fine, but sometimes this isn’t good. This was one of those times where it wasn’t good: instead of having (what I imagined I would have) a lot of time to myself to spend however I want during my time off from work (truly, I envisioned having like 10-12 newsletters ready-to-publish, which is totally unrealistic, but what I imagined nonetheless) I noticed myself spending an inordinate amount of time prepping for our trip.
The good news? I noticed and I did something about it (why is this actually way harder than it should be?) In the days leading up to when we left, I got through the bulk of the big things remaining (packing for myself & then editing what I set aside to pack) and then out the door to do some things that I actually wanted to be able to do by setting a timer for myself and getting as far as I could in 30 minutes (you can’t kill the productivity princess!!)
The packing…it’s a process! Doing a good job packing for any trip takes time, practice, discipline. I have a pared down process these days - but it does feel luxurious and fun to take the time to pull things out, try them on and think about what I’m going to wear. A little try on is always a mood-booster! The funny thing about this trip in particularly, is that even though I will carefully pack outfits I’m looking forward to wearing and that are curated for our planned activities, the truth is, as soon as we’re at the Lake, I’ll spend most of my time in a bathing suit and shorts and an easy button up on top, and either a bucket hat or a baseball cap on, with no shoes. (Note: I originally wrote this the week before we left, and now that we’re back, not only can I confirm that I spent my time mostly wearing that exact same thing, I can also be mad at myself for not taking my past self’s advice!)
I could probably pack 4 bathing suits, a button up and one dress and be totally fine (that is not me, but, it could be, you know?) Every evening at the end of the day I will take a glorious post-waterfront-day shower, scrub off sunscreen, and sand, and lake water, and put on clean clothes of the easy linen-pants and a t-shirt variety and it will be perfect. We will spend a few days with friends before we go all the way north, so I will get dressed on those days, but once we’re at the Lake, its as casual as casual can be. A very unfancy vacation. Which is, honestly, perfection, or, at least a version of it (because, there are many ways to do a perfect vacation - I can think of several!)
I am happy with this! This trip that we do in the summer time, to my in-laws cottage on Lake Michigan, is a trip to my husband’s favorite place in the world. He grew up spending his summers there, we went there all-year-round when we were dating and got engaged, and now he gets to share it with his kids. It is low-key and casual and artsy and relaxing. Waking up and seeing a gigantic body of water immediately is IMPORTANT. As a born-and-raised coastal girl, I will love the ocean forever and ever but man is there something about the lakes in the Midwest. Especially Lake Michigan. It’s good for your soul.
I can’t help myself though, I am imaging other summer vacations that I would love to take someday - some with no kids, some with kids when they are perhaps a little older. As I sorted through my closet finalizing my suitcase (and then editing, and editing again, because I have limited space, and the three car seats aren’t going to carry themselves through the airport), I had to force myself to be honest about the question - “am I actually going to wear this on this trip?” And so, I put a lot of things back (not everything because I like to have a little choice on my vacations, especially ones that are over a week long, even if it means an extra piece or two in my suitcase). That act of putting things back, it made me think of the occasions that I could wear those pieces and outfits for - what those vacations might look like, be like, feel like.
Unsurprisingly, I came up with several - more of a vibe, or a “what it would be like,” than a specific destination or trip. When I was thinking about vacations I was surprised that there actually aren’t that many places I think of specifically visiting in summer (perhaps because I have spent most of my life living in New England and cherishing the good weather when it comes, I’ve mostly traveled locally in the summer time, and ventured to further away locations in different seasons), but, I am not one to say no to a good fantasy trip, and someday I hope to have the ability to make trips that are like these ones (regardless of the time of year in which is happens!)
So, here’s to fantasy trips and the things I would actually wear (and pack!) for them! Plus, my styling notes — how to create some of these looks with things you probably already have, or how I would wear them outside of vacation.
If you’d like to shop all the pieces featured in a single place, you can do that here.
Fantasy Trip #1: Lakeside days, afternoons spent meandering through art galleries and small shops, wrapped up with sunset cocktails on the dock
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This is my current summer expedition, and this is essentially exactly what I’m wearing. This matching set is expensive (this top and pants is similar and much less expensive option!), but the quality is beautiful and you’ll get a ton of mileage out of it. The full set can be worn to travel, and anything you need to be wearing something more than a bathing suit. Wear the pants with your bathing suit out to dinner or drinks (toss the sweater over your shoulder!). You can throw the button down over your suit when you need a break from the sun.
Create a matching set of your own — choose a shirt and pants that are the same color (I think black or navy is the easiest), or, pick pj pants and your favorite button down!
I love this tote so much, it’s on my wishlist. Here’s something at lower price point that I also love.
Fantasy Trip #2: New England seaside town: mornings are spent playing tennis and riding bikes, afternoons spent playing sand sports at the beach, and evenings spent devouring as much fresh seafood as you can stomach, playing cards and sipping cocktails late into the night
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This will be my next summer expedition - In August, we go to the cape with my family, but this could be a trip to the Cape, Maine (pictured), Rhode Island, New Hampshire… I will (again), spend a lot of time in my bathing suit and a button-down, but, we will have easier access to go for a quick bike ride to get coffee or ice cream or head out for a bite to eat, so while it’s certainly not fancy, I will put on real clothes every few days or so. A button down with jean shorts is quintessential summertime, and I’ll wear it as much as possible. I’ve found jeans shorts to be hard to shop for in the past, and finally figured out to just size the heck up - I wear this pair 2 sizes larger than my normal pair - they’re loose everywhere, but in a great way.
I love a waistcoat and love it especially paired back to a skirt, but if you don’t have one, you could easily pair the button-down or even just a simple tank with a skirt, plus your favorite necklaces for a night out.
Fantasy Vacation #3: Boat days spent lounging then traveling to boat-only access dinner locales for feasts, champagne and dancing and (hopefully) spotting celebrities
I’m not sure where this vacation is, exactly. I think I’m imaging somewhere in Europe - maybe Croatia (pictured)? Maybe Greece? Maybe Italy? Maybe Malta or one of those other amazing places in the Mediterranean? It doesn’t matter because this is a luxurious but laid-back vacation. Lots of time spent on the water, but also lots of time wearing chic outfits that make you feel your best.
This is a great opportunity to wear your shortest, skimpiest dress that you might have trouble wearing in your day-to-day life as a coverup (put a bathing suit underneath anything and it’s appropriate! And, I freaking live for a fun pant (these are on sale!)- so this is your chance to wear them with a white tank, or a simple tee, or even a bikini top!
Fantasy Vacation #4: European Beach-side town where you put as much thought into planning what you’re wearing to spend a day at the local beach club as you do into what you’re wearing to the club after
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This is the type of vacation I want to go on either with just my husband, or with a group of girlfriends (manifesting this for us!). The type of trip where you can wear all your most favorite pieces and get super dressed up and everyone else around you will be equally dressed up and inspired you with everything they’re wearing. It’s definitely in Europe because they do beach clubs better than anyone else (pictured: Cefalu, Sicily)
In my opinion, this is about pushing the limits - wearing a combination you might not wear at home (looking at you mini skirt with bikini top, if that makes you nervous, add a button down on top - but, leave it open!), but, in the best way possible.
Fantasy Vacation #5: Summer in a city, seeing the sites, checking out the local spots and spending days browsing museums, cool shops and the best bars and restaurants
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Any city, anywhere (pictured: Madrid). Cities get a bad rep in the summertime, which I get, because people want to be on a beach or waterfront when it’s hot, but there is something really special about a city in the summertime. So much to explore outside. You can eat all your meals on patio - you can’t beat that people watching. Or, maybe this is a great staycation. I’m not sure it’s a staycation for us necessarily because we still have a little drive to get to Boston, but we honestly love heading in for the day. Just a little break from your routine and a chance to wear something special that makes you feel great.
You want to be comfortable, but you also want to feel great, and, most importantly, not too hot. I love a mini dress (similar at a lower price point!) with sneakers - you can go super minimal and just change your shoes & handbag (use code CHRISTINA15 for 15% off at Jenn Lee!) for a dinner out, or you can switch things up and wear a statement outfit!
That’s all for today. Thank you so much for reading! I would love it if you would share my Substack with a friend who might like to read (and subscribe!) - I write weekly about personal style, getting dressed to feel my best, making the most out of the clothes we have, shopping with intent, and what’s going on in my life.
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Ok I needed to read this!!! Going to my parents’ for 5 days before my brother’s wedding in Dallas - they live on a lake, and I’m desperately trying to pack just a carry on for me and the baby 🫠🫠 Schipol Airport has been having checked bag issues so I don’t want to risk it!! Your packing process and what you wish you’d done post trip is going to be my guiding light!!!