We are embarking on a brief weekend getaway to Ashland for the Shakespeare festival, which means it’s time to pack for the weekend. This summer, we have two family road trips planned, both within California – one for family reasons. Our itinerary includes a mix of city and countryside destinations such as San Francisco, Santa Cruz, Monterey, Carmel Valley, Tahoe, the Redwoods, and a small dude ranch. As a family, we prefer to travel light and only carry on our luggage, except for winter trips that require bulky snow gear. Packing light for family trips has always been easy for us and simplifies our lives. My priority is to be comfortable, stay true to my style, and feel somewhat stylish at the same time.
Two Favorite Dresses
When the nights get cool, I like to have something to cover my legs and arms. Instead of opting for pants, I prefer to wear a flowy and flattering dress. I have a pink dress that I’ve owned for years, which has a slightly tropical vibe and is perfect for summer nights in the city. It comes in different fabrics, but I prefer the satin modal for its drapey quality and the fact that it requires no ironing. The black linen dress has been a surprising favorite for me. Despite not usually wearing black due to how it looks on camera, this dress is special. It’s linen, super drapey, and oversized – I even had to size way down to XXS.
Weekend Packing: Blousey And Breezy Tops
My preference for blouses leans towards loose and boxy styles with a bohemian touch, perfect for vacation. I love the puff-sleeved Isla top from Emerson Fry for its flattering fit, fun patterns, and breathability. Another favorite is a breezy white shirt from Target that I’ve worn multiple times both on vacation and at home this spring.
This breezy white shirt from Target has absolutely checked the box so many times. I’ve worn it a ton, both in Mexico on vacation and just around here this spring.
I plan on bringing two classic white shirts that go with ANYTHING. This linen shirt is new to me and fantastic – the most perfect texture and drape, and I love the boy pocket. I tried the Quince one, and it was good for the price, but this J.Crew one is simply better. The camo shorts are awesome (size down) and so easy to wear. Y’all, the J.Crew one is on a huge sale, $70 right now.
Weekend Packing: Favorite Jean Shorts
I have two shorts that I pack no matter what – these Agolde Parker shorts (sits nicely on the hips, flares out, perfect hem a bit oversized, so very comfortable) and the Gap bermudas (a bit of a stretch, so very comfortable, longer, great distressing). I have quite the denim shorts collection, but these two are the ones that I grab the most and are the most comfortable and cool.
A 10/10 for denim comfort (stretchy, roomy but still flattering).
Weekend Packing: Two Easy-To-Layer Cardigans
I also struggle with cardigans as I am a bit bulkier up top, so I don’t love to wear really thin fitted ones. This one from Aritzia is awesome and roomy, but cropped and has thinner sleeves. I sized up to a Medium to be able to layer over easier, and yet it’s still thin enough that it can handle a jacket over it.
The Quince navy cardigan is thicker, but great for nighttime, and really classic and chunky, but with such a great cut and high-quality knit.
Weekend Packing: Comfortable Pants
These cargo pants are fantastic. They are on the thinner side, so really great for warmer weather, but they aren’t cheap and flimsy. They have great structure even after washing (and versatile – cool around town but also easy to hike in). You can tie the bottom or not. They are low-waisted and sit so easily on the hips. 10/10. I love that Gap sweatshirt, BTW, it has the most perfect wash and retro 70s fit. And those are my favorite sunglasses that I have 4 pairs of because they are polarized, so lightweight, and stay on your face really easily (and under $40).
These are fantastic for casual anytime wear pants. So comfortable, flattering, great pockets, etc. I bought them in the lighter stripe as well.
Lastly, if I were to bring jeans, I’d choose between these two:
Quince black Washed denim Bella Crop: These are already heavy in rotation and are super comfortable and cool. They have enough stretch in them to be all-day jeans. If you want to splurge, these Mother jeans are fantastic. Also stretchy with that perfect hem and stitching at the ankle. These are the only two pairs of jeans I would attempt to bring on a casual vacation.
One of my favorite pull-on pants EVER just came back in stock in a new colorway. I don’t have a professional shot of me wearing them, but these are perfect weekend/vacation pants that are a little splurgier than the above, but Emerson Fry does everything so well that they’ll last for years.
Weekend Packing: Comfortable Shoes
Now this is where I can get greedy and bring too many, but it’s so important to have the right shoe. This is very trip-dependent, obviously.
The huarches and the mules (below) are probably redundant – both easy to dress up and down, both neutral, both super comfortable. But also both are very small to pack, so easy to bring them.
For sneakers, I’ve been wearing my cobalt Nike Pacificas, and I just bought them in a maroon leather and the darker green for days where I want them to blend in more. Cute for city walking + good enough for 2-3 mile hikes with the kids.
I will also bring my Tkees flip flops and my Nike slides. If I want to bring any heels its likely a cushy platform from Korkease. My mules are no longer on sale, but I want THESE so bad and might get. And again, the leopard-strapped birks from Kelsey Dagger are a nighttime go-to that is casual but still really stylish.
Weekend Packing: New Linen Jacket
I’ve worn this outfit so many times. Same long sleeve t-shirt, same shorts, but this linen jacket dresses it up a bit, and the color is perfect (just really complements most of what I have and breaks up the blue). Of course, now I want to pack those ballet flats, too! I’m in the market for a chore jacket (I have my eye on this one). I bought this denim one from Quince, and it’s AWESOME, but it’s a bit thick and stiff for summer wear, and I’d rather wear a canvas version.
Now, to be clear, I fully overpacked for two nights in Ashland (thus the trap of a car trip). Have a fantastic Memorial Day weekend, folks. Summer is here 🙂
*Photos by Kaitlin Green