We are headed out on a quick weekend away (Ashland for the Shakespeare festival), which means…weekend packing. This summer we have two family road trips (both in California, strangely – one is family related) with a mix of cities and relaxed country (SF, Santa Cruz, Monterey, Carmel Valley, Tahoe, the Redwoods, a small dude ranch, etc). We are a “carry-on” family and try our best not to check anything (outside of winter trips that involve bulky snow clothes). In general, for family trips, packing light feels easy to us and just simplifies our lives. I mostly want to be comfortable, look like “me’ while yes, feeling kinda stylish.

Two Favorite Dresses

Pink Dress (available color) | Black Dress

I find that regardless of how warm it is, nights cool down enough to warrant something on my legs and arms, but why wear pants when you can wear a super drapey and flattering dress? The pink one I’ve had for years and leans slightly “tropical” but is also great for a city summer night (it comes in different fabrics – cotton, linen – but I much prefer the “satin modal” for the drapy-ness and zero need to steam or iron). It’s called the Lucy 4, and they make different colorways every season, and I love their new green one and just bought it because it reads even less tropical. The black linen dress is a shocking sleeper hit for me (I tend not to wear too much black because it doesn’t read that well on camera and it washes me out, but this dress is so special). I wore it 4 of the 8 nights in Mexico for dinner – and on the plane both ways. It was between 65-75 at night and offered the perfect amount of coverage without needing to layer over. Great for a city vacation, too. Linen and super, super drapey. Oh, and size WAY down, I’m wearing the XXS, and it’s still oversized.

Weekend Packing: Blousey And Breezy Tops

White Blouse | Blue Top (similar)

I like my blouses more loose and boxy, erring on bohemian over structured for vacation. Emerson Fry makes the best, and I can’t believe I don’t have any photos in my favorite one – the puff-sleeved Isla top. It’s always flattering, the patterns are fun and not too loud. Plus, it’s super airy and breathable (they also have a long-sleeve version). That blouse above is a different version, but it gives you an idea. The prints are always fantastic, and the cotton is super high quality and yet not too thick (easy to tuck, never too long, etc).

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.

Linen Blouse | Camo Shorts | Shoes

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.

Hat | Scarf | Shirt | Bag | Pants | Shoes

This button-up is another really thin and breathable, but falls well (doesn’t tug or hug) and is easy to layer. It’s truly so lightweight and easy to wear in warmer climates if you want some coverage. The fabric is almost like a seersucker, so you don’t have to iron it. And yes, those linen pants will never miss a vacation with me again. So comfortable, cute, breathable, easy to throw on, flattering, and cute pockets. That belt bag is my favorite.

Striped Top

I find it hard to find a long sleeve that has the right weight – that isn’t too thick and hot (or hard to layer over) or too thin and shows everything underneath. I bought two of these in different colors and have worn them a lot. I love that it has a stripe but isn’t too thick and bold, just subtle. Notice the drop shoulder. Also, that photo cracks me up. It’s giving 90s Martha Stewart catalogue.

Weekend Packing: Favorite Jean Shorts

Agolde Parker Long Shorts | Shirt | Sandals

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. Also, I’ve been wearing the hell out of those sandals – they make any boring outfit (like the one above) so much more interesting. I wouldn’t wear them for an 8-hour city walk day, but I wore them most nights in Mexico for dinner.

Bermuda Denim Shorts

A 10/10 for denim comfort (stretchy, roomy but still flattering).

Weekend Packing: Two Easy-To-Layer Cardigans

Scarf | Sunglasses | Cardigan | Pants

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. Nothing flashy, but man, so easy to wear.

Sweater | Jeans | Belt | Bag | Sandals

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. It’s perfect for those 60-degree nights instead of a jacket. It reminds me of Jenny Kayne’s knitwear, but 1/8th the cost.

Weekend Packing: Comfortable Pants

Sunglasses | Sweatshirt | Pants | Shoes

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).

Left: Hat | Shirt | Pants | Sandals | Right: Cardigan | Pants | Shoes

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

Linen Jacket | Long Sleeve T-Shirt | Jean Shorts | Shoes

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