Unless otherwise specified, all sizes in this post are listed in women’s.
1. A butterfly satin beauty to set your heart and your vacation wardrobe all aflutter.
Lisa Says Gah is a woman-owned small business that's a one-stop shop for products created and designed by independent artists and designers.
Get it from Lisa Says Gah for $168 (available in sizes XS–3XL).
2. A vintage floral long-sleeved midi dress in case you get chilly easily and prefer something with a bit more fabric.
Promising review: "I purchased this as a last-minute dress for a wedding. It was snug above the waist, but not snug enough where I was uncomfortable or had no movement. It fit perfectly!! The material is not cheap, it’s a nice, soft material, and you can have confidence it won’t fall apart in the washer or anything! Love it. I’ll probably buy another one in a different pattern." —Liz Garcia
Get it from Amazon for $28.99+ (available in sizes S–XXL and 18 patterns).
3. A crisscross maxi dress in a sunset ombré pattern you'll want to wear when you head out for pre-dinner cocktails at the tiki bar.
Promising review: "Purchased online and am so happy I did!!! The ombré colors are beautiful and vibrant. It's such good quality and a thick (not see through) material. I was unsure about the straps across the chest but it adds a very feminine feature. Can’t wait for summer to wear!" —Liz705
Get it from Torrid for $68.40 (originally $85.50; available in sizes 10–30).
4. A stunning ruffled option you'll want to strut down the streets in when styled with some chunky wedges.
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Promising review: "I can’t say enough good things about this dress! I love it!! The fit is amazing. The material is lovely. The top, front, and bottom of the dress are lined with a light material, which is perfect. You still get the flowy feel. I just want to twirl around in this dress. My young adult daughter loves it as well!! I couldn’t be happier. It will be my go-to dress this summer" —Carla J. Reid
Get it from Amazon for $42.99 (available in sizes S–XL and in six colors).
5. A floral wrap dress since you can't go wrong with the iconic, classic wrap silhouette and a floral pattern. A truly unstoppable pair.
Promising review: "I searched through about 300 'cocktail dress with long sleeves' options before finding this gem! The material is great — it stands up to wrinkles, long car rides, and doesn’t cling at all. The cut is (really) low so I got some skin/fabric tape to close it up. I love it!" —Amazon Customer
Get it from Amazon for $19.99+ (available in sizes 4–22 and in 22 prints).
6. A bell-sleeve embroidered tunic dress that'll work day or night with a solid pair of sandals or heels.
Promising review: "I really do love this dress. (I got the black one with red floral embroidery.) I've worn it to dinner and on a cruise. I can probably wear it to a wedding or a beach party. You can dress it up with heels or wear flat sandals with it. I even wore it with my Chucks and it looked adorable. No accessorizing needed, but you can throw on a simple necklace and go. So easy! (Quality also seems good. Thick material = no bra necessary for me! Yay!!)" —Poupee Folle
Get it from Amazon for $22.99+ (available in sizes XS–XXL and in four styles).
7. A ruched bodice sundress with gorgeous button detailing that looks like you spent major bucks (and time) digging for that perf vintage wardrobe piece.
Promising review: "I absolutely love this dress! It looks just as pictured. The material is of good quality and thick enough not to be see-through, yet not too heavy, and it’s very well-made." —Dee Alvarez
Get it from Amazon for $19.90+ (available in sizes S–XL and in 23 colors/prints).
8. A cottagecore floral tiered dress that's adorably trendy and oh-so-twirlworthy.
Get it from Forever 21 for $24.49 (originally $34.99; available in sizes 0X–3X and two colors).
9. A faux-wrap midi dress you don't have to worry about popping open in the bust area (this has happened to me far too many times) since it's...not a real wrap (shhhhhhh).
Promising review: "I bought this dress for a professional conference in a few weeks. The dress looks perfect. It goes to my knees and the chest area is very modest and appropriate for my conference, but if I throw on a statement necklace it could just as easily be something I wear to a musical or nice event. The fabric doesn’t stick to anything, and I’m pleasantly surprised at how thick the material is. I don't need a slip or undershirt." —Skye C.
Get it from Amazon for $32.99 (available in sizes 14–26 and in 25 styles, including some with three-quarter sleeves).
10. A tie-front cutie if you're looking for a new addition to your closet that says "Let's pack a bag and jet set off to the French Riviera."
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
The straps are adjustable. Also, note that the tie is just for show on some styles, but on others it's real!
Promising review: "This dress was the best online purchase of a dress in my life!!!!! It’s a perfect fit! It’s beautiful!!! Very flowy. I am sooooo shocked that this purchase was so successful, because usually clothes don't fit me when I buy them online." —Mariam
Get it from Amazon for $22.99+ (available in sizes XS–XL and in 33 colors/prints).
11. A romantic smocked midi for a sweet shoulder moment that can be effortlessly paired with a denim jacket. I'm all for an off-the-shoulder look so this will be added to my cart immediately.
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Reviewers say it generally runs true to size but a bit on the looser side.
Promising review: "This dress was made for me. Listen, guys, saying this dress is beautiful is such an understatement. Listen, it's the middle of the night and I'm feeling myself. Just wait till it's morning; the looks I'm serving all of you! Update: So I ended up buying three different colors of these dresses. I just loved them all. It's like the designer thought of me when they made these dresses! The material feels great on my body. The upper part is stretchy and fits very well." —Olive Bukuru
Get it from Amazon for $32.99 (available in sizes XS–XL and in eight colors).
12. A polka dot pattern midi style with a sultry V-neckline in case you're not feelin' a mini dress but also not feelin' a maxi dress (midi dresses are my personal favorite).
Get it from Unique Vintage for $78 (available in sizes 1X–3X).
13. A ruffled, open back maxi dress that's incredibly dramatic, romantic, and effortless.
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Promising review: "This dress is absolutely stunning! Love how flowy it is, the bohemian look, and how sexy the back of the dress is. Received so many compliments. Perfect dress for a vacation. Bought it for my trip to Bali and couldn’t be more pleased." —Carolina Orozco
Get it from Amazon for $34.99 (available in sizes S–XL and in 24 colors).
14. A boho-inspired flare dress for a light and airy option that pairs well with a woven handbag.
Promising review: "Love love love it! Totally worth the price. It has a zipper so it’s easier to get on. The straps are hard to tie in a cute bow by yourself; it’s definitely easier with someone’s help. But this dress is so cute, just buy it!" —Shelby Dixon
Get it from Amazon for $24.99+ (available in sizes 0–10 and in eight styles/colors).
15. A splurge-worthy Selkie dress that's what fantastical, pastel, fairy dreams are made of. If you're anticipating something special on your next trip, pack this lil' beauty.
Selkie is a woman-owned clothing brand that is owned by former Wildfox co-founder Kimberley Gordon. Her designs are super whimsical and romantic.
Promising review: "Absolutely fell in love with this dress after it arrived! Fit like a glove and made me feel angelic. The material felt very high quality for organza and it maintains its shape very well! I have five dresses now since I'm obsessed." —Abril
Get it from Revolve for $249 (available in sizes 4–16).
16. A ruffle-sleeve cotton dress that's simple but brings the fun with its flouncy sleeves. Add a sun hat and you're good as gold.
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Promising review: "This dress is incredible! Material is very good quality and it fit perfectly! I cannot wait to wear it!" —Amazon Customer
Get it from Amazon for $45.98 (available in sizes S–XL and 14 colors).
17. A strapless maxi dress perfect for anyone looking for a stretchy option. No matter where the day heads, you can count on being comfy and cute.
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Promising review: "Love love love this dress I purchased from Amazon! I want to thank all the people who left picture reviews that helped me decide to purchase this lovely find! This dress fits a little on the larger size, but I love the comfort. The material feels really nice against the skin and it's not see through either!" —Gayla Williams
Get it from Amazon for $32.99+ (available in sizes S–XXL and in 28 colors/prints).
18. A lantern sleeve midi dress in a fun colorful striped pattern you won't be able to get enough of. You'll feel like a modern day Audrey Hepburn — on holiday of course.
Mr. Water New York is a New York-based Etsy shop featuring a ton of gorgeous clothing pieces with a vintage feel.
Promising review: "I absolutely love this dress!! I get so many compliments when I wear it and it’s truly one of a kind." —Victoria Kennedy
Get it from Mr. Water New York on Etsy for $89 (available in sizes S–XL).
19. A strapless maxi dress with romantic ruffles along the neckline and a regency-era feel.
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Promising review: "I ordered the apricot dress and it fit perfectly. I got so many compliments! Now I just need to figure out what other color to order." —sharon
Get it from Amazon for $15.69+ (available in sizes S–XL and in 19 colors/patterns).
20. A striped wraparound dress in case you love matching your wardrobe to the weather of your destination — AKA, warm and sunny.
Promising review: "Love this dress. Have wanted it for a while but was scared it would be too short. It fits just right. It's so soft. Love the way it feels on my skin. It doesn't feel cheaply made at all. Would definitely buy in a different color! If you're looking at this dress and are on the fence about buying it, just buy it! You won't regret it!" —Ashley
Get it from Amazon for $12.99+ (available in sizes S–XL and 11 colors).
21. A stunning cocktail dress for an elevated option to keep on hand in case your partner is surprising you with a fancy din din.
Promising review: "Love this dress! It was a great price for a last minute request for being a bridesmaid in a friend's wedding. This is very comfortable and you won't be sorry if you buy it." —RockyMtnGrrl70
Get it from Amazon for $46.74 (available in sizes S–XL and nine colors).
22. A smock mini dress ideal for layering under a cute denim jacket that says, "I'm on island time!" 🌸
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Promising review: "I LOVE this wrap dress! The material is so soft and comfortable, and the dress is a perfect fit. I always try to find dresses that would be work appropriate and also cute to wear if going out after work and on the weekends, and this fits the bill." —Taylor
Get it from Amazon for $27.99+ (available in sizes S–XXL and in 22 colors/styles).
23. A ruffle sleeve mini dress in case your closet is begging for a daytime staple that feels flirty and fun.
Promising review: "This dress is so cute and the material is great for how cheap it is! I was so impressed by the quality. I ordered a size bigger than normal and I probably could have gotten my normal size but I wanted to have it a little longer so I could wear it to work!" —Gracyn Herman
Get it from Amazon for $24.89+ (available in sizes S–XXL and 11 colors).
24. A groovy mini dress featuring a sassy cowlneck that'll put all of your other vacation 'fits to shame.
25. A classic blouse dress that's a classic for a reason. With this dress as your canvas, you can add all your fun accessories from a bold belt, to a bright handbag.
Promising review: "Material is great, soft, and the fit is perfect to wear with a nice pair of boots, etc. I sized up and it was a good fit." —Donna Jarock
Get it from Amazon for $32.99 (available in sizes S–XXL and in 15 colors).
26. A flowy ruffled-hem dress you seriously can't go wrong with, regardless of the weather where you're traveling. It can be worn with sandals or cozied up with tights and booties!
Psst! This dress is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Promising review: "I absolutely love this dress — it fits perfectly and it's so adorable. The first day I wore it I got so many compliments and it was so comfortable. It was nice to wear as a dress or even a long shirt with leggings. The color is really cute too. I definitely recommend it and will probably buy more in different colors!" —Jasmine Ball
Get it from Amazon for $26.99+ (available in sizes S–XL and in 17 colors)
27. A satin blue dress in case any fancy dinners are on the agenda and you want to look like a Parisian royal.
Simple Retro is a woman-owned brand that was created by a group of friends with a passion for thrifting and a common mission to create clothing that would be timeless beyond seasonal trends. They are based in NYC.
Promising review: "This dress is super stunning and comfortable.Got so many compliments! The midi length mixed with the strapless slip is the perfect combination of sexy. The fabric is soft and comfortable." —cocomaisonave
Get it from Simple Retro for $44.99 (available in sizes XS–L).