Top 20 Getaway Dresses for Your Upcoming Vacation
“Ree mentions that you’ll immediately feel like you’re in the mindset of a summer getaway.”
Each product featured here has been handpicked by a member of The Pioneer Woman’s editorial team. Purchases made through selected links may generate a small compensation for us.
Exciting news—you’re heading off on a getaway! Whether it’s a seaside holiday with the family or a couples’ retreat, you’ll have a blast enjoying the sunshine and unwinding however you please. You’ve already picked out your favorite cozy travel clothes for the journey, but the real dilemma is: What should you bring and wear once you arrive? Our suggestion? Include a few adorable summer dresses in your luggage—easy to slip on for a stylish, carefree vibe.
Ree Drummond shares the same sentiment. “I aim to travel light and only bring items I adore,” she says, such as the outfit she chose for Mexico. “Vibrant, airy maxi dresses are enchanting: They effortlessly transition from the pool or beach to dinner or a party.” She’s absolutely correct! That’s precisely why we’ve curated the top vacation dresses currently on the market—effortless, lightweight, and incredibly versatile. Our selection features charming floral designs, tropical-print dresses that exude beachy vibes, and, naturally, a handful of timeless striped options.
While many of our selections are , you’ll also discover a few stylish midi dresses that are perfectly on-trend. The collection includes comfortable smocked dresses ideal for warm weather, along with designs featuring flattering flutter sleeves and relaxed elastic waists. The best part? These versatile pieces can easily transition from vacation to everyday wear. “Pick one of these charming options, and you’ll feel like you’re on a summer getaway in no time,” Ree suggests. We couldn’t agree more! Time to prepare fordressplanning a getaway.
- Top 15 Straw Hats for Ultimate Sun Protection
- 12 Supportive Flip-Flops Designed for All-Day Comfort
- 12 Perfect Matching Family Swimsuits for an Adorable and Stylish Beach Outing
Corfu Weekend Linen Mix Thin-Strap Shift Dress
This dress will transport you straight to Greece—if it doesn’t, we’re not sure what will. (Well, perhaps a flight could. 😉) The lightweight linen blend ensures you stay cool in the heat. Time to enjoy a cocktail at the hotel’s patio bar!
Bryson Flared Jumpsuit
Lilly Pulitzer never fails to capture the essence of a summer getaway! This design stands out with its adorable romper underneath, offering just the right coverage when those ocean winds pick up.
Elegant One-Shoulder Tropical Ruffle Maxi Dress
Though we couldn’t locate the precise dress she wore during her trip to Mexico, that stunning palm print remains unforgettable. If you’re just as captivated, take a look at this one-shoulder alternative—equally vibrant and tropical!
FARM Rio Blue Tile Fantasy Long Dress
Like mother, like daughter! Both Ree and Alex have been spotted wearing dresses by FARM Rio. This particular design features an off-shoulder neckline with voluminous sleeves and a vibrant blue print, reminiscent of Alex’s recent trip to Cabo San Lucas, Mexico.
Bsubseach Kaftan
Searching for a dress that also works as a swimsuit cover-up? A kaftan is the perfect choice! Its loose, airy design ensures you stay cool and can conceal sweat when necessary. Don’t forget to explore the variety of prints available for added style!
The Ellie Nap Dress
No collection of summer dresses is finished without the highly sought-after Nap Dress. Its smocked bodice ensures exceptional comfort, while the fluttering sleeves add a touch of elegance. Plus, the soft pastel design radiates effortless charm!
Boho Long Maxi Summer Dress
This palm leaf print dress will make you feel as if you’re in a tropical paradise… and it’s just $20! The flattering halter neckline and adorable waist-cinching bow add the perfect touch.
Layered Midi Dress
Experience the essence of Hawaii no matter where you are with this vibrant tropical print design. The adjustable straps and relaxed fit ensure both comfort and a flattering silhouette for every wearer.
Smocked Handkerchief Hem Midi Dress
If bold, bright colors aren’t your style, these shades will still work beautifully! This handkerchief hem dress strikes the ideal mix of snug and relaxed, ending just above the ankle—no matter your height. Available in petite, regular, and tall sizes.
Elegant Floral Wrap Dress
Wrap dresses effortlessly enhance your silhouette with their timeless charm and grace. The addition of delicate flutter sleeves elevates the design to another level of elegance. With a selection of more than 30 stunning prints and solid hues, there’s a perfect option for every style preference.
The Somerset Maxi Dress
If you haven’t bought The Somerset dress already, we believe this is the perfect moment! It’s Anthropologie’s most-reviewed dress.ever, this fresh lemon print stands out as one of the finest available.It’s available in both petite and plus sizes as well!
Hollie Midi Dress in Shadow Stripe
Featuring stylish flutter sleeves and a midi length, this dress ensures you stay fashion-forward during your getaway. Though the floral pattern is charming, the delicate shadow stripe on the material stands out as the highlight.
Tiered Maxi Dress in Double Cloth Fabric
You don’t have to rely on prints to capture that holiday feeling. A timeless white option, like this airy choice, works just as well! The easygoing cut and lightweight material ensure you stay cool and self-assured in warm weather.
Kimono Maxi Dress in Printed Design
Celebrate the timeless charm of the kimono-style dress! Designed for comfort with a relaxed fit, it accentuates your shape through a tailored waist. The vintage-inspired pattern is a favorite, though you can explore more than 30 alternative designs to suit your preference.
Kenzo’s sleeveless poplin cotton dress featuring blue and white stripes
Blue and white stripes evoke a classic nautical feel, making them ideal for summer vacations that honor the spirit of the good ol’ USA. Simply pair them with red accents, and your look is complete!
Strapless Belted Long Dress
Luxuriously smooth material, a figure-flattering tied waist, and an ideal shade of pink for the season—this dress is undoubtedly designed for getaway vibes. Don’t miss the four additional color choices, each uniquely vibrant and full of playful charm.
Fit & Flare Sleeveless Midi Dress
This dress is perfect for anyone heading out on a trip―and we truly meananyoneThe garment comes in sizes ranging from XS to 4X, with options for regular, tall, and petite lengths. Its adjustable straps enhance customization for a perfect fit.
Loose-Fitting Short Sleeve Maxi Dresses
We love how effortlessly wearable this dress is. It feels as cozy as a T-shirt yet offers a touch of extra flair. The blue and white pattern is ideal, though you can explore over 40 additional choices if you prefer something different.
Scoop Satin Mini Dress with Delicate Ruffles
For a shorter option, check out this stylish piece! Crafted from satin fabric, it effortlessly transitions from day to night—just pair it with heeled sandals for an elegant evening look.
Boho-Inspired Sleeveless Tie-Dye Maxi Dress
Even if prints are a favorite, there are moments when only tie dye will do—and a getaway is the perfect opportunity. This relaxed cotton-blend maxi dress features handy pockets and is available in a wide array of patterns and colors.
AnnMarie Mattila serves as the Commerce Editor at The Pioneer Woman, where she writes about a variety of products, including home goods, fashion, beauty, and other categories.
Belle Bakst is a fashion editor and content creator based in New York City. Her writing and creative projects have appeared in publications such as Cosmopolitan, InStyle, Harper’s Bazaar, and Brides. Outside of scouting the season’s top footwear trends, she often documents sample sales on her vlog or hunts for thrifted treasures across Manhattan. For style inspiration, vintage jewelry finds, and the occasional Bergdorf Goodman snapshot, follow her on Instagram and TikTok at @littlefashionstylist.
