10 Summer Dresses Our Editors Are Packing for Vacation

My ideal summer dress is an old man’s nightshirt, in the style of Grandpa Joe from Charlie and the Chocolate Factory. Collared, cuffed and breezy are my three keywords, and they are all fulfilled by this shirt-dress from H&M which is (technically) a nightshirt. I wore it all last summer, through a pregnancy, an unprecedented heatwave, and even to leave the labor ward post-baby. It’s wonderfully flappy, looks just as good crumpled as it does ironed, and I even like to style it over jeans or slacks for a kind of Copenhagen-er vibe into early September. My particular nightshirt isn’t available anymore, but I love H&M’s linen and have my eye on this wheaten option for this coming summer.

My favorite summer dresses are those that are versatile enough to wear gardening and then dress up with a sandal or block heel for a dinner date or even a wedding. I got this one in black about a year ago — when I found out I was pregnant with my son — because it has a fitted but stretchy tank bodice with straps wide enough to conceal any bra straps and a full, very breathable cotton skirt. I knew it would fit me (and be comfortable) throughout my pregnancy and after the baby. Most days, I wear it with a chambray button-down shirt thrown over top as an extra layer to block the sun or insulate me from AC. It is amazingly flattering: No matter how tired or frazzled I am, this dress makes me feel put together and sexy in about 30 seconds.

In the summer, I wear this dress at least twice a week. I have had it for more than three years and have worn it while traveling, on bike rides, as a beach cover-up, to work, and out for drinks. It’s the dress I reach for whenever the temperature goes above 90 degrees because no matter how much I sweat, the fabric keeps me feeling dry and breezy. Plus it looks great with sneakers, sandals, heels, and even Blundstone boots. You can buy the Dawn dress in a bunch of different colors and patterns; I have it in a navy-blue-and-black check that isn’t available anymore. But this black-and-white gingham is a pretty close match.

I prefer dresses over every other type of garment because they’re one piece and I’m lazy. I bought older versions of these dresses during a sample sale five years ago, and they’re a constant for me during the summer. I just throw these on and go. Because the colors are pretty neutral and the length mid-calf, I’ve even gotten away with wearing these in the fall with black tights and a Barbour jacket. They’re easy to pack on trips, and because they’re linen, they look fine crumpled. (For more affordable linen dresses, I turn to Etsy: either Yayi and Pony or Linen Clothing by Anny, which made me a custom dress based on a Daniela Gregis design.)

This is a wedding staple for me. I first bought it when I was pregnant with my second child and wore it to my cousin’s California desert wedding. It’s super-flattering with a bump because it’s a wraparound style that can be adjusted, has a square neck and structured cap sleeves, and Angelina Jolie–esque side slits. It can be dressed up or down depending on the accessories you pair with it and is just a really great dress. I’ve worn it in the winter, too, with tights and a cardigan.

I’m a big proponent of slip dresses, and there’s no dress in my closet I wear more than Cou Cou’s cami slip. I got it in black, and it’s the perfect LBD; it’s sleek, minimal and lightweight, so it’ll take up barely any space in your carry-on, and it’s made from 100 percent organic cotton, so won’t wrinkle even if you ball it up. I style it with a big necklace and cowboy boots or kitten heels in the summer, then in the fall I’ll layer it with tights, a turtleneck, and an oversize sweater.

Ahead of last summer, I did a walk-through of the new Buck Mason designs and came away with this dress. We talk a lot about their T-shirts on the Strategist, but this dress is everything. It’s a simple ribbed knit basic tank dress with a few details that make it a standout. It’s quite long and hits right at my ankle, which is very flattering. This, combined with the high neck and the way the straps cut in a bit, add so much versatility to this dress. I can wear it very casually with Converse, but I have also dressed it up with heels and a blazer or shirt. The straps have this nifty snap to secure your bra strap in, hiding them and absolving you of fussing with a strapless.

I even threw a sweater on top and wore it with boots all through the winter. This season, Buck Mason came out with another version of the dress that has a lot of the same features but more of a mermaid skirt that adds a healthy dose of whimsy — I now have that too.

Ahead of a recent bachelorette party that called for a “bright, colorful outfit” for one of the nights, I thrifted this dress on the Real Real. It’s fitted without feeling too restrictive, thanks to its slightly stretchy material, so I was able to move (and dance) in it very comfortably. Despite my aversion to longer dresses, this one doesn’t feel like it’s swallowing me whole because of its flattering high-neck, low-back cut. The material’s thick enough that I can wear it without a bra but doesn’t feel stuffy on warmer days. Even though I originally bought it for a night out, I’ve worn it to casual picnics since and gotten compliments on it every time.

I feel giddy when I get the chance to wear this dress. The skirt is gloriously puffy, but the slinky jersey bodice tempers the grandness into something more casual (and hugs my chest very flatteringly — it’s definitely a no-bra situation). As it’s so dramatic, I’ve already paired it with kitten heels for a party, but on my upcoming trip to Paris, I’m going to style it with some New Balances for a more relaxed day of sightseeing. The wine shade really complements my hair (I’m a redhead), and the straps add even more romance when they’re tied into two dangling bows. The only danger of wearing this dress is that it becomes endlessly tempting to break out into pirouettes just to feel the way the breeze sways along the hem.