Cafe Leandra Exclusives

Great summer dresses and how to wear them

by Leandra Medine Cohen
If you buy something, I might earn a commission.

There is no easier way to reconcile getting dressed to look put together with as little effort as possible as wearing a dress. In the summer, this proposition is particularly seductive because it’s also hot as hell, and a one-and-done dress might well be the most efficient way to stay as cool as possible.

The exception to this rule is an in-between concoction of tank shorts and button down/boxer set but I sense a shift coming in how well want to convey ourselves through clothes in the coming months — a bit less laid back, more done up/thought through, even if we don’t want the mental effort to change.

But the thing with a dress is that it says so much, leaves so room to convey your sense of personal style lest you style it up with layers and stuff, which no when it’s this hot. Don’t underestimate what a pair of sunglasses or necklace or a bag and especially, specifically, a pair of shoes can do. Below, some great dresses (most on sale) and the shoe styles you could pair them with to achieve the highly desirable state of looking nice with a rough edge.

Cutout Floral-print Cotton-poplin Maxi Dress
$371 USD

Why it’s good: Primarily because it’s a naked dress that actually does a decent job of covering you up. The print is ditzy and subtle enough to warrant wear by even those among of us who refuse them. I’d probably just hem it slightly so you could see more of my ankle.

How to wear it: A pair of unexpected sunglasses like these and either closed-toe shoes like these or ballet flats (to make it feel less beach-y if you’re in a city. If you’re not, enjoy your flip flops!)

Lumière cutout metallic stretch-knit maxi dress
$247 USD

Also a big fan of this one for $247 — like I might get it if I can find my size.

Orelle Nightgown
$168 USD

Why it’s good: The most efficient solution to summer heat by a landslide. Slight enough to weather and even soften sticky skin, an interesting case study in what you can do under it as opposed to over it and of course, because in-between dressing is in.

How to wear it: Anything goes with this one — I like mine with a pair of mocassins or ballet flats and these sunglasses. When I do this, I usually hold a straw basket. If I’m going the way of sandal (closed-back flat or wedge mule), I like a leather bag to anchor the look/make it seem more intentional than just me house-clothes.

Other good silhouettes for the nightgown: this one from Etsy, this one from Salter House, this one from If Only If.

Poppy Buttercup
If Only If
$168 USD
Sisters Nightdress
Salter House
$88 USD
White Cottagecore Cotton Sleepwear
$69 USD

Christopher Kane
Bridal Lace Crystal Mesh Minidress
$1,164 USD

Why it’s good: The way my closet is structured (so much denim and suede, lots of button-down shirts, flat shoes, tons of play jewelry), it’s easier to dress down a garment than it is to dress it up. This doesn’t work with all silhouettes — the shape of the garment you’re dressing down has to be amendable to styling, which a slip dress is. So that makes it fun to style with and around, and also a (distinctly) strong enough contender for main event.

How to wear it: For now, with plain closed-back sandals and a shacket. Or I’d wear it solo with black loafers, white socks and a suede jacket or something army green in the fall. Will be nice with black tights and black platforms (suede ideally)/a blazer for the holiday season. Also a loose-enough fit that it could be good with the right cotton pants underneath.

Maison Cleo
Coral green shiny sequins backless mini dress
$223 USD

Alternatively, there is always this, which for the current season you can fashion the same way.

Alaa Printed Satin-twill Kaftan
$614 USD

Why it’s good: Because you literally don’t have to do a thing other than lift your arms to get this one and look like you’re put together. The print is tasteful, the fabric’s luxurious and depending on what kind of shoes you pick, you can wear it all day or out to dinner.

How to wear it: Lace up flat sandals for day (these on the expensive end, these on the not), wedge mules at night.

Floaty Gathered Midi Dress
$135 USD

Another contender to fulfill the same purpose: this one from Cos.

J. Crew
Bubble-skirt A-line Mini Dress In Cotton Poplin
$148 USD

Why it’s good: Mostly because it seems like exactly the kind of easy dress one desires to wear to work in the summer but also because I’d absolutely wear it, and don’t work in an office. That means there’s good overlap on the Venn diagram of style and practical purpose!

How to wear it: White socks, black loafers (or sneakers) —the way Olympia (creative director at J. Crew) did with a blazer. Knee-high black flat boots or cowboy boots in the fall, sheer socks, and black patent slingbacks then too.

Maeve Cutout Bubble-Hem Dress
$148 USD

If you want something a bit less conservative, this one from Anthropologie looks nice.

Jean Paul Gaultier
+ Lotta Volkova Layered silk-satin and Crepe Midi Dress
$995 USD

Why it’s good: It’s a more structured slip dress with a lot of personality, and falls into the category I mentioned above re: something easier to dress down than up. With this dress, it’s substantial enough to hold its own — like truly does not need to be messed with. Just wear the right shoes (denim or suede flats for day, a slingback sandal for night with a necklace on a cord like this or this)

How to wear it: See above! You might want to add a basket bag too.

Vivi Polka-dot Cotton And Silk Minidress
$268 USD

Why it’s good:

..But also, the shape! It makes for a really good foil to low-heel platforms like these or these.

How to wear it: Wayfarer-style sunglasses, ballet flats, tennis shoes (navy blue Supergas), the aforementioned low-heel platforms

Square-neck Denim Mini Dress
$135 USD

Why it’s good: Originally it was this jumpsuit that made it to the list because nothing is easier, actually, than one small but roomy piece of fabric that covers your body in all the right places. It wears well with a pair of clogs and some kind of tote you would use for a farmer’s market, but when I saw the dress I figured, +1 for it being easier to go to the bathroom in it too. And I think the dark denim makes it a more versatile option —you can carry it into the next season and it will look right at home with like, a brown suede bomber.'

How to wear it: I keep messing this up by putting the styling notes in the Why but for now, in addition to clogs (or any kind of low-heel platform) how about with these? I also love it as shown with a low-heel open-toe mule.

Robe chemise en popeline de coton rayée Chloe
$242 USD

Why it’s good: It has pockets, a bib, is a faint and delectable shade of blue stripe and is not too long to style under a pair of pants, or too shirt to wear on its own.

How to wear it: I’m looking forward to wearing it with knee-high boots and a crewneck open-hem sweater next fall, and until then, it’s mostly pants like these with flip flops.

Ruched jersey mini slip dress
$508 USD

Or left open with something tiny — think a dress like this — under.

La Double J
Apron Dress in Palmetto Placée
$820 USD

Why it’s good: I would be remiss to leave my collab dress out, which is good because: completely exposed upper back in the most flattering way for even a woman like me with low-grade scoliosis and a statement unto itself in a pleasantly precious way (takes pressure off everything else you wear with it) and it was made by a group of seamstresses who are currently incarcerated but members of Coopertiva Alice, an organization that furthers the pursuit of rehabilitation for women in the Sant Vittore prisons of Milan by teaching its members how to sew so they can earn a wage for their work.

How to wear it: Flip flops, loafers, fisherman shoes!

Wild cards:

Rotate Birger Christensen
Nunni Paillette-embellished Recycled-tulle Midi Dress
$336 USD

Would wear this one with a white shacket and lace-up sandals like these.

Crystal-embellished Ponte Jersey Minidress
$556 USD

It has served me well so far this season — through the spring it was a great base layer for a fringe jacket and this season I’ve been wearing it with button-down shirts over. You could make the case that it would also be great tucked into a mid-length pleated skirt. Dare I say a sheer one?

Renaissance Renaissance
Cold-shoulder Tulle-trimmed Cotton-poplin Maxi Dress
$540 USD

Not even sure what to say about this one it just made me smile.

But that concludes this edit. Have a good one!