5 Vacation-Worthy Summer Dresses

Five of the season’s new warm-weather frocks, each ideal for a holiday locale. What if—we asked ourselves—those dresses sent gloating messages to the poor clothes left back home?

Photo: F. Martin Ramin/ The Wall Street Journal, Styling by Jill Telesnicki
Tooty Fruity Flavor in San Miguel de Allende, Mexico

Dear Closet,

Naturally, I fit right in here in Mexico with my sunny, fruity, flowery print, like a Frida Kahlo painting minus the brooding glare. How’s life back there in the dark?

XO, D.R.S.

This voluminous pineapple-printed beach-to-bar dress is a cinch—especially when tied with its extra-long braided belt. Ella Dress, $385, matchesfashion.com

Photo: F. Martin Ramin/ The Wall Street Journal, Styling by Jill Telesnicki
Twisted Prep in Nantucket

To all my clothes-est friends (ha!),

Not to brag, but all the preppy, stripe-y dresses in Nantucket look so dull next to me. None of their stripes are as playfully twisted and ruffled. Of course, speaking of dull, I’ll soon be back there with you poor guys and that stuck-up shoe rack.

Love, D

A mid-calf-length dress that takes something great about New England’s classic seashore style—stripes—and twists them up just enough to look cool again. Steady Dress, $450, Rachel Comey, 212-334-0455

Photo: F. Martin Ramin/ The Wall Street Journal, Styling by Jill Telesnicki
Flitting Romance in Big Sur

Hi Closet,

Life in Big Sur is such a blur. As a suitably carefree and boho dress, I’ve been much in demand for selfies with ocean views. I get a break tomorrow bc she’s going to a nudist colony. I miss you all. The moths, not so much!

Ciao! Dressling

An eyelet-edged lilac midi dress laces up the back for a completely unexpected dash of skin that is ideal for dinner above the fog at the Post Ranch Inn. La Vie Dress, $375, rebeccataylor.com

Photo: F. Martin Ramin/ The Wall Street Journal, Styling by Jill Telesnicki
Kawaii Playfulness in Tokyo

Closet Gang--

The good news: I look adorable shopping in Ginza. The bad news: I ripped slightly during an exuberant karaoke outing. I’m so sore! Can’t wait to get back to the rack and relax.

X Dress

A silk minidress that checks boxes you never knew needed checking (but do): ’70s-style graphic print, rugby-band arm stripes, mirrored discs on the skirt and a delicate lace hem. Shirt Dress, $2,750, Chloé, 212-717-8220

Photo: F. Martin Ramin/ The Wall Street Journal, Styling by Jill Telesnicki
Minimalism in Copenhagen

Hey Closet:

I can sum up Copenhagen in three words: So. Much. Bike-riding. My side-slits have really come in handy. As has my simple aesthetic. Danes aren’t big into clutter or mess. They’d have a lot of trouble with our sad friend, the jewelry drawer.

Fondly, Frock

A fresh, button-up shirtdress that tempers light white cotton with fine black stitching along the edge. Two slits, one tie-belt, lots of buttons, not many dollars. Creased Dress, $70, zara.com

More in Style & Fashion