A woman in a yellow floral FAITHFULL THE BRAND Esperanza Maxi Dress, perfect for a city break, is walking across a paved area with scooters parked in the background, under a clear sky.


The Dress Edit

Going Away? Here Are The Best Designer Dresses For A City Break

It’s time to plan those much-needed spring and summer getaways… and I’ve found all the best dresses for a city break to pack before you go. From flitting between coffee shops and sipping drinks on the river to strolling through picturesque town squares, these simple yet stylish silhouettes can do it all. Stock your suitcase with floral midi dresses from Faithfull The Brand, Johanna Ortiz, and Doen, but don’t forget those simple, block-color designs by Free People, Tularosa, and Melloday. All you’ll need then are the perfect shoes and accessories to finish off your looks. And yes, I’ve shopped for the hottest designer flats, heels, and handbags to take with you too!

A person in a long-sleeved DÔEN Odelette dress, perfect for a city break, stands on a sidewalk with their face tilted upwards and eyes closed, basking in the sunlight.


A woman in a JONATHAN SIMKHAI Gwynn V Neck Midi Dress with black lace trim, ideal for a city break, standing against a dark brick wall.

@jonathansimkhai / Instagram

Designer Day-To-Night Dresses For A City Break

With just a few days and nights to play with, I love finding dresses for a city break that take me seamlessly from day to night. Like the Gwynn V-neck midi dress by Simkhai. Style this simple, slip-on dress with flats or heels and a classic evening bag for the ultimate afternoon/evening look on your trip. The Quasimodo croc-effect sandals by Giuseppe Zanotti and Voyou leather shoulder bag by Givenchy will accentuate the lace detailing, They’ll also go with every other dress you bring with you.

Meanwhile, lovers of prints (and open-back silhouettes) will adore the Regina midi dress by Faithfull The Brand. This eternally stylish midi calls for low heels and a versatile leather bag to accentuate the brown print. That’s what makes the Harlow brown leather slingback sandals by The Row and Loewe’s Hammock hobo mini bag the perfect accessories to style it with.

Shop more Dresses For A City Break selected and reviewed by our expert fashion buyers and stylists

  • DÔEN Haleigh Dress

  • ALIX OF BOHEMIA Kaia Shirred Printed Cotton-voile Midi Dress

  • MATTEAU Shirred Cotton Midi Dress

  • ENGLISH FACTORY Tie Back Knit Maxi Dress

  • MELLODAY Stripe Shirt Dress

  • JOHANNA ORTIZ Pradera Geometric-print Linen-blend Midi Dress

  • ROCOCO SAND Mia Long-Sleeve Ruffled Maxi Dress

  • Adoni Sleeveless Mesh Midi Dress

  • TULAROSA Asa Mini Dress

  • FAITHFULL THE BRAND Bellavista Midi Dress

  • FAITHFULL THE BRAND Palacio Midi Dress

  • FAITHFULL THE BRAND Regina Midi Dress

  • FAITHFULL THE BRAND Camera Midi Dress

  • FAITHFULL THE BRAND Esperanza Maxi Dress

  • JONATHAN SIMKHAI Gwynn V Neck Midi Dress

  • DVF Erica Cotton Dress

  • HUTCH Sleeveless Square-Neck A-Line Maxi Dress

  • PETAL & PUP Kelda Floral Midi Dress

  • FREE PEOPLE Cypress Lace Maxi Dress

  • ZIMMERMANN Matchmaker Broderie Anglaise Cotton Midi Dress

  • FAITHFULL THE BRAND Las Mayas Midi Dress

  • FARM RIO Pineapple Lace-trimmed Smocked Broderie Anglaise Cotton Maxi Dress

  • DÔEN Tahlia Printed Dress

  • DÔEN Odelette Dress


Designer Dresses For A City Break You'll Reach For On Repeat

Are you packing light and looking for dresses you’ll want to wear repeatedly on your trip? Or, do you want to invest in styles you’ll still happily reach for after the vacation’s over? Either way, you’re in the right place. Firstly, dresses like the Odelette midi by Doen will see you stylishly through everything from grabbing your morning coffee on the square to afternoons spent taking in the sights. Also, you’ll also be slipping into this pretty floral silhouette for brunch dates and other weekend plans back home. So, grab a simple leather bag and pair this dress with chic designer boots or flats according to the weather. The buckle Ballerina Naplack flats by Ganni and small Arlene crossbody bag by Chloe will look incredible with this dress.

Finally, don’t go anywhere without the Tahlia dress, also by Doen. This must-have midi goes with everything from flats to boots to heels. Additionally, it’s the ultimate day-to-night dress and will be a go-to for summer and beyond. My advice? Get your hands on the Anemone wedge sandals by Ferragamo and the Neeson tassel woven leather shoulder bag by Anya Hinmark.  It’s the ultimate city break ensemble, not to mention, those block heels are perfect for cobbled streets!

Shop All Dresses For A City Break

A woman in a Faithfull The Brand Regina Midi Dress perfect for a city break and sunglasses is crouching on a concrete surface with her head turned to face the camera.

Faithfull The Brand

A woman with curly hair is captured in mid-motion on a city street, wearing the Going Away? Here Are The Best Designer Dresses For A City Break DÔEN Tahlia Dress and a black coat, with an old doorway in the background.


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