A woman in a Fall Vacation Dress For A Seriously Stylish Trip stands on a rocky coastline at sunset, with the sun low in the sky behind her, casting a warm glow.


The Dress Edit

Fall Vacation Dresses For A Seriously Stylish Trip

Jetting off for a little fall break before winter comes? We have the fall vacation dresses you need! Whether you’re heading for the sunshine or slightly cooler climes, you’ll find the ideal silhouettes for your trip below. We’ve done the hard part for you and searched the world’s leading online fashion stores for all of this season’s must-have dresses. Keep scrolling to discover our top picks from Farm Rio, Dôen, La Ligne, Ba&sh, and so many more. Secure them now and wear them for many vacations to come!

A woman in a "Fall Vacation Dresses For A Seriously Stylish Trip" stands confidently in a sunlit room with lush greenery in the background. She sports large, round sunglasses and has curly hair.

Farm Rio

A woman stands on a balcony, wearing a colorful, patterned Fall Vacation Dresses for a Seriously Stylish Trip with thin straps. She holds a woven hat and gazes downward, surrounded by greenery and architectural elements.

Charlie Holiday

Designer Fall Vacation Dresses With Sleeves

As the cooler temperatures creep in, we’re looking for fall vacation dresses designed to suit the weather outside. In particular, those with sleeves we can wear for city breaks and fall beach vacations alike. For example, the Kaftan dress by Hemant and Nandita. This stunning pink dress with a mixed pink floral print will be your go-to dress on any fall vacation. Firstly. it boasts long blouson sleeves that are perfect for the time of year but are also oversized for a laidback vacation vibe. Secondly, the plunge V-neckline and maxi skirt with a split mean they look just as good with flats and sandals as they do with heels. So, you can style them for both your daytime and evening plans on your trip.


Meanwhile, the Cerere belted printed silk-voile maxi dress by La Double J is the ultimate vacation maxi. From the stylish high neckline and maxi-length skirt to the neutral colorway and contrasting deep red tropical print. We adore everything about this dress and highly recommend you give it a top spot in your suitcase this fall.

Shop more vacation dresses selected and reviewed by our expert fashion buyers and stylists

  • ZIMMERMANN Matchmaker Linen & Silk Mini Dress

  • ZIMMERMANN Matchmaker Picnic Linen Midi Dress

  • DOLCE & GABBANA Cotton Poplin Flower Print Mini Dress

  • GIAMBATTISTA VALLI Printed Silk Georgette Maxi Dress

  • SALONI Lea Printed Silk-jacquard Midi Dress

  • ALESSANDRA RICH Rose-print Silk-crepe Maxi Dress


  • FOR LOVE & LEMONS Leighton Mini Dress

  • GUCCI Horse-print Silk-twill Shirt Dress


Pretty Fall Vacation Dresses For Every Vacation Plan

Whether heading for a stroll along the beach or dressing for dinner, these fall vacation dresses will make you feel your most stylish. Firstly, don’t go anywhere without the Wendelin dress by Doen. We’re head over heels for the adorable ruffle detailing and muted yellow print. These work just as well for late summer days as they do for fall ones. What’s more, this dress looks just as perfect with sandals or bare feet as it does with boots and knitwear. The ultimate transitional dress for fall vacation days!


Alternatively, when you’re dressing up for dinner, we highly recommend the Sonali cotton and silk-blend midi dress by Ulla Johnson. From the chic lace panels and soft cream colorway to the long-sleeve and mid-length skirt, this dress stuns from every angle. Pair yours with heels for a dressy ensemble or slip on flat sandals for an effortlessly stylish, low-key evening look.


Shop All Fall Vacation Dresses

A woman in a yellow Fall Vacation Dresses For A Seriously Stylish Trip walks along a sandy beach at sunset, holding sandals in one hand, with boats visible in the distant water during her fall vacation.


A woman in a Fall Vacation Dress For A Seriously Stylish Trip stands on a wooden deck overlooking a beach, with the waves crashing onto the shore in the background. Her gaze is directed towards the ocean, and her hair is styled.


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