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Best Travel Dresses for Every Season by a Frequent Traveler

If you’re searching for the best travel dresses that are wrinkle-resistant, versatile, comfortable, stylish, have pockets and are great quality – this is the post for you! Plus, these are dresses that are being tested and worn by an actual traveler on adventures (me – the voice behind Have Clothes, Will Travel!)…and not just a random roundup featuring product photos from a mysterious writer.

Some of the dresses in the post I’ve had for years and have worn on adventures ranging from sightseeing in Russia to lounging on the beach in Jamaica to riding camels in Egypt. Some are more recent finds.

I will be briefly reviewing and answering each question below for the dresses/brands featured in this post, as these are what I look for when buying a dress for traveling.

  • Is it wrinkle-resistant?
  • Is it versatile?
  • It is comfortable (breathable)?
  • Which season(s) does it work for?
  • Does it have pockets?
  • How good of quality is it?
  • Is it machine-washable?

Please feel free to reach out if you have any questions about the travel dresses featured in this post in the comments section at the end. Enjoy!

*Disclosure: some of these links are affiliate links. Meaning, if you click a link and make a purchase, Have Clothes, Will Travel gets a very small commission at no extra cost to you. Thank you for supporting the brands that make this blog possible!

The Best Travel Dresses for Every Season and Trip

SCOTTeVEST – Dorothy Dress

Is it wrinkle-resistant?

Sort of. I wouldn’t say this dress is 100% wrinkle-resistant. However, I didn’t iron it before wearing it in the photos featured here (but you can see some wrinkles).

Is it versatile?

Yes, with the right accessories – I’ve worn this SCOTTeVEST dress from sightseeing to dinner and even as a swimsuit coverup. It’s come with me to the Caribbean, throughout the US, Brazil, and recently on a safari in Kenya.

It is comfortable (breathable)?

VERY. This is the most comfortable and breathable dress in this entire post.

Which season(s) does it work for?

Spring, summer and early fall. This dress is pretty lightweight, even with layering, I think it would get a little chilly in the dead of winter.

Does it have pockets?

Yes – and they’re the best pockets on this list too! They actually zip, so your belongings stay safe AND dry. I was caught in a crazy rainstorm by Christ the Redeemer (in Brazil) while wearing this dress and my passport and phone were both fine and dry in my pockets!

How good of quality is it?

Amazing! This dress is really well-made and the design is incredibly well-thought-out for a traveler. I’ve had it for a few years now and have worn and washed it dozens of times and it is holding up super well.

Is it machine-washable?

Yes. It also drys SUPER fast, so if you’re caught in a rainstorm or want to wash it in a hotel sink… this dress will be dry in couple hours.

SCOTTeVEST - Dorothy Dress
SCOTTeVEST - Dorothy Dress
SCOTTeVEST - Dorothy Dress
SCOTTeVEST - Dorothy Dress
SCOTTeVEST - Dorothy Dress
SCOTTeVEST - Dorothy Dress

SCOTTeVest is best known for their revolutionary travel eVEST that has a pocket for just about everything! However, they also make many other clothing items, such as this lovely Dorothy dress that features 4 pockets and is loose-fitting and stylish to boot.

I was seriously blown away by how comfortable this dress is – and how quickly it dried after I was drenched in a storm. (I didn’t even change for dinner that night!) The pockets are also the best-designed pockets in this entire post (they kept my passport, phone, and credit card safe and dry).

And while being loose-fitting is super comfortable, I do prefer this dress paired with a belt (just my personal preference). You can also get a slightly more fitted look if you size down a size when ordering.

Use code HCWT for 15% off your order!

SCOTTeVEST – Daisy Dress

Is it wrinkle-resistant?

As with the SCOTTeVEST dress above, I would not say this SCOTTeVEST dress is wrinkle-resistant, but it doesn’t show wrinkles too badly either. Before I took these photos, I sat in an airport/airplane for hours and then hopped off the plane to explore Denver, and I didn’t think you could see any noticeable wrinkles on this dress.

Is versatile?

In my opinion, yes. This dress is easy to dress up with jewelry and accessories – but can also easily be dressed down with flip-flops or sneakers. Once it cools down I also plan to pair this dress with boots and a cardigan.

It is comfortable (breathable)?

Yes. I wore this dress in 90-degree heat last week and was comfortable in it. This is a bit thicker of a material, though than my other SCOTTeVEST dress. I do think it is still comfortable in warm weather, though.

Which season(s) does it work for?

I would say all of them. This dress is thick enough to work in winter with a pair of tights, boots, and a cardigan. I’m really excited about how versatile this dress is!

Does it have pockets?

Yes! It has 8 pockets total. While I think the hidden pocket on the back of the dress is kind of silly – the other pockets in the front are very useful for travel. (My recent Reel shows this dress and its pockets off a little better.)

How good of quality is it?

This is a very high-quality dress. The thought that went into designing and creating this is very evident. It’s definitely one that is going to last many years to come. (I would suggest sizing down, though, if you want a more fitted/flattering fit. I prefer my travel dresses a little looser, though.)

Is it machine-washable?

Yes, I’ve been washing it on a regular cycle with cold water and it is holding up perfectly. I don’t put this dress in the dryer, though. (I don’t dry any of these dresses, actually.)

SCOTTEVEST travel dress worn in Denver by Have Clothes, Will Travel
SCOTTEVEST travel dress worn in Denver by Have Clothes, Will Travel

SCOTTeVEST gets the first 2 spots on this list because I am so happy with the quality of their dresses and how practical they are for travel. I know these aren’t the world’s sexiest dresses, but when it comes to travel clothing – I’m more for usefulness than anything. SCOTTeVEST travel clothing in general is very high-quality and a brand I really like to use when traveling.

Tentree – Ribbed Tank Dress

Is it wrinkle-resistant?

No. HOWEVER, once I put this dress on I can’t see any wrinkles due to it being so stretchy. I never iron this dress and I had it rolled into a little ball in my suitcase before I put it on here.

Is it versatile?

Yes, this is another dress that is easy to dress down with flip-flops or sneakers… or dressed up with nice flats or wedges and some fancy accessories. It can easily be paired with a jean jacket or cardigan for cooler weather too.

It is comfortable (breathable)?

Yes! This dress is super comfortable and breathable. It’s also a VERY stretchy material. This is the yoga pants of dresses right here!

Which season(s) does it work for?

I would say spring, summer, and fall. Although, with the right pair of boots and a cardigan this could work in winter too. I think pairing it with tights, though, might look a little strange, given how fitted it is.

Does it have pockets?

No, unfortunately.

How good of quality is it?

This is another high-quality dress that has been holding up very well for a variety of adventures!

Is it machine-washable?

Yes, but again, I don’t dry this dress.

Tentree Ribbed Tank Dress
Tentree Ribbed Tank Dress
Tentree Ribbed Tank Dress
Tentree Ribbed Tank Dress

Tentree is a brand that is committed to sustainability – which I love. This dress is made with cotton that was grown without the use of synthetic pesticides, herbicides and fertilizers. This dress comes in red as well, and I like this black version of it so well, I just might have to get the red one too.

Carve Designs – Lyla Dress

Is it wrinkle-resistant?

Yes! That was the main reason I ordered this dress. It appeared to be a lightweight material that wouldn’t wrinkle, and that was indeed the case.

Is versatile?

In my opinion, yes. This dress is easy to dress up with jewelry and flats or wedges – but can also easily be dressed down with flip-flops or sneakers. I also like the way this dress looks with a cardigan. It works great for a night out, but could just as easily be worn to the beach.

It is comfortable (breathable)?

Yes. This dress is super comfortable and breathable. I love it for a hot summer day or for a tropical vacation. This dress is something that I can easily nap in it’s so comfortable. (It’s actually made out of recycled swimwear, so it dries quickly too.)

Which season(s) does it work for?

I would say spring and summer. This is definitely a dress that is designed to be worn in warm weather. It would be tough to transition this one to fall/winter.

Does it have pockets?

No, unfortunately. That is the only thing I don’t like about it. The design of this one would be perfect for pockets too…

How good of quality is it?

This is the newest travel dress that I’ve added to my wardrobe. I’ve had it for just a few months. However, as far as first impressions go, I would say this is a very high-quality dress. I also have several other clothing items from Carve Designs that I absolutely love.

Is it machine-washable?

Yes, but I also do not dry this dress.

a Closeup of the Lyla Dress
the back of the Lyla dress
the lyla dress fir travek

Carve Designs is a company I have really come to love for its comfortable, quality clothing. I started with jeans and a top from this company and now own swimwear and also this dress. They’re fantastic! This dress is unique compared to the rest of them in this post too because it comes with a built-in floating shelf bra. I, personally, still need to wear a bra with it for adequate support, though.

Karina Dresses – ALL of Their Dress Styles!

Note: this one isn’t for a particular style of dress as ALL of the dresses made by Karina Dresses work well for traveling. (I currently own 5 of their dresses in different styles.)

Is it wrinkle-resistant?

Yes! All the dresses made by Karina Dresses are wrinkle-resistant and packable!

Is it versatile?

Yes, I have worn my Karina Dresses for every type of event under the sun.

It is comfortable (breathable)?

YES. These dresses are SO comfortable and breathable.

Which season(s) does it work for?

Every season! I’ll show photos below, but these dresses work from winter-summer no problem! Just pair with tights or a cardigan in winter and you’re good to go (pictured below).

Does it have pockets?

Some of their dress styles do have pockets, but not all of them do.

How good of quality is the dress?

All of the dresses I have from Karina Dresses are of incredible quality. The one in the photo above in Russia I’ve worn and washed at least 30 times and it still looks new. They are also all made in the USA!

Is it machine-washable?

Yes! All Karina Dresses are machine-washable.

A Stylish & Packable Travel Dress (With Pockets!)
Karina Dresses Review
Karina Dresses
Honest Review of Karina Dresses - Vintage Style Dresses That Don
travel dress

Karina Dresses are my go-to for travel dresses. They check every box that I look for in a travel dress. I also love that they are a small, US-based company that is committed to creating quality dresses in sizes that range from XXS-4X. All of the dresses above are from Karina Dresses. I also wrote an in-depth review of Karina Dresses – if you’re interested.

SCOTTeVEST – Long Sleeve Daphne Dress

Is it wrinkle-resistant?

As is the case with my other SCOTTeVEST travel dresses, I would not say this is 100% wrinkle-free. But despite this dress being stuffed in my duffle bag and not ironed before I put it on for these photos, I don’t think it looks too wrinkled.

Is it versatile?

Yes! This dress is easy to wear casually with sneakers or flip-flops. However, it can also be dressed up with pumps or leather riding boots. I also like wearing this dress in winter with fleece-lined tights and combat boots (see below).

It is comfortable (breathable)?

This is a very comfortable and stretchy dress. It is soft and cozy with light-fleece brushed inside. However, I don’t know if I would say it’s breathable. This dress is designed to be worn in cooler weather.

Which season(s) does it work for?

Fall, winter, and early spring. This dress is definitely suited for cold weather. I would say it’s the best winter travel dress on this list. I would not wear this one in the dead of summer, though.

Does it have pockets?

Of course! SCOTTeVEST items all have great pockets. This dress has 4 pockets, including a small one in the sleeve for tissues or a card.

How good of quality is it?

Fantastic! I really love SCOTTeVEST for their dresses and outerwear. They’re all fantastic quality and are really thoughtfully designed for traveling and overall functionality.

Is it machine-washable?

Yes. No special care is required for this dress.

Back of the SCOTTeVEST - Long Sleeve Daphne Dress
SCOTTeVEST - Long Sleeve Daphne Dress paired with a black scarf
Showing the Daphne dress in a jumping pose with white sneakers

You really can’t go wrong with any of SCOTTeVEST’s dresses for travel. This one would also be great for an office setting if you need to travel for work.

Use code HCWT for 15% off your order!

Anatomie – Travel Marine Wrinkle-Free Wrap Dress

Is it wrinkle-resistant?

Yes! This dress is 100% wrinkle-resistant.

Is it versatile?

Yes! I’ve worn this Anatomie dress for a day of sightseeing through Rio de Janeiro to dinner at a fancy steak house in the city.

It is comfortable (breathable)?

Yes, it’s very comfortable and breathable. The humidity in Rio was insane (I mean, check out my hair! Haha.) and I was still comfortable wearing this dress.

Which season(s) does it work for?

While I’ve only worn this dress in spring and summer so far – there’s no reason you couldn’t pair this dress with boots and tights for winter. I’ll test it out in some chillier weather when I head to Ireland!

Does it have pockets?

Unfortunately, no. That is the only thing I don’t like about this dress.

How good of quality is it?

FANTASTIC. I think this dress is the highest quality dress on this entire list.

Is it machine-washable?

Yep!

Wearing my Anatomie travel dress out a fancy, schmancy dinner
Anatomie - Travel Marine Winkle-Free Wrap Dress

Anatomie is a brand that specifically makes high-quality, luxury travel clothing for women. This is my only dress from Anatomie at this time, but that is going to have to change! I LOVE how stylish and classy this dress is. It’s super flattering and would work on just about any body type too. It also comes in red and navy.

(Pro tip: be sure to wash this Anatomie travel dress before wearing it. I literally took it out of the package and threw it in my suitcase the first time I wore it… and it ended up bleeding on the light-colored bra I was wearing. However, I wore it in some really humid and sticky conditions, and also was caught in a couple of rainstorms. Still, it’s better to just be safe than sorry – just wash it first!)

United by Blue – Ridley Long Sleeve Swing Dress

Is it wrinkle-resistant?

Sort of. I wouldn’t say this dress is 100% wrinkle-resistant. However, I didn’t iron it before wearing it in the photos featured here (but you can see some wrinkles). I did not wash this dress or pack it in any special way, though.

Is it versatile?

Not exactly. This dress works great as a casual clothing item. But you’re not likely going to be wearing it to the office or a fancy dinner.

It is comfortable (breathable)?

Yes! It is so soft and comfortable. It feels like being wrapped in my favorite blanket snuggled on the couch.

Which season(s) does it work for?

Spring, early summer, fall, and winter. This dress from United by Blue is one of the thickest dresses on this list. So, I think it works great in chillier weather with layers. It’s not so thick, though, that it can’t be worn in warm weather either. (I wore it as a swimsuit coverup above in 75-degree weather.)

Does it have pockets?

Yep!

How good of quality is it?

It’s fantastic quality, and it’s also made from sustainable materials.

Is it machine-washable?

Yep.

United by Blue - Ridley Long Sleeve Swing Dress
United by Blue - Ridley Long Sleeve Swing Dress
United by Blue - Ridley Long Sleeve Swing Dress

United by Blue is a clothing company committed to making the world a better place. For every product you purchase from United by Blue – they remove one pound of trash from the ocean. Plus, their clothing is high-quality and made from sustainable materials. Their Ridley dress is perfect for a beach vacation or if you’re embarking on a camping trip. I’m also bringing this dress along for St. Patrick’s Day in Dublin next year. I think it will be perfect with leggings and boots for the celebrations!

XCVI – Bran Dress

Is it wrinkle-resistant?

No. This dress will require a good steaming before you wear it.

Is it versatile?

Not exactly. I don’t think this dress will work for an office or a fancy dinner. It’s great to wear exploring or for more casual events.

It is comfortable (breathable)?

Yes. This dress is very comfortable and breathable.

Which season(s) does it work for?

Spring, fall, and winter. I don’t love wearing this dress in super hot weather.

Does it have pockets?

Yes! And they’re huge!

How good of quality is the dress?

This dress is really good quality and is a really interesting design.

Is it machine-washable?

Yes!

XCVI Clothing - Full Review of Tops, Bottoms and Dresses From a Frequent Traveler
XCVI Clothing - Full Review of Tops, Bottoms and Dresses From a Frequent Traveler
XCVI Clothing - Full Review of Tops, Bottoms and Dresses From a Frequent Traveler

XCVI is a brand that prides itself on being “fashion you can live in.” I am a huge fan of their leggings for traveling and also like this particular dress for the right travel adventure because it is comfortable, has such deep pockets, and hides the dirt well! I think it would be great to wear for a safari-type vacation or any sort of outdoorsy trip. (I also wrote an extensive review of XCVI clothing.)

Milumia – Boho Split Tie-Waist Maxi Dress

Is it wrinkle-resistant?

No. This dress will need to be ironed.

Is it versatile?

Yes! I’ve worn this dress by Milumia for everything from running errands to riding camels in Egypt and also for nights out at nicer restaurants.

It is comfortable (breathable)?

Yes, it’s very comfortable and breathable. It’s a very lightweight material.

Which season(s) does it work for?

Summer and spring and fall. This dress is great for hot weather but works in cooler weather when paired with a jacket, scarf and boots.

Does it have pockets?

Yes!

How good of quality is it?

It’s OK quality. I’ve worn and washed this dress around a dozen times now and some threading is coming undone (easy enough fix). But I don’t foresee this dress lasting as long as the other ones listed in this post.

Is it machine-washable?

Yep!

Milumia is a fast-fashion clothing company that makes boho dresses for very affordable prices. You’ll find them on websites such as Shein or Amazon. I like these dresses for traveling in warmer climates as they are super comfortable and affordable. I actually own a total of three of these short-sleeved Milumia maxi dresses, just in different prints. I had purchased them all for my trip to Egypt.

Milumia – Button-Up Split Floral Print Maxi Dress

I also wanted to include this dress by Milumia because I get SO much use out of it. I’ve had it for years and have worn it from adventures in Argentina, Turkey, Egypt, Russia, and more. All of the points are the same for this Milumia dress as the one above (so, I’m not going to repeat them), except that this dress seems to be far better quality. I’ve had it for around 4 years now and still looks like new. It also does NOT have pockets, unfortunately.

Shein floral maxi dress for fall
Most Versatile Maxi Dress
shein floral button maxi dress
What I Wore to the Egyptian Museum in Cairo

*Some of the dresses in this post were gifted to me for past collaborations. However, this blog post is NOT sponsored by any company. I wrote it because I wanted to share my favorite travel dresses with fellow explorers… and there really seems to be a lack of posts like this on Google that actually show the dresses in action!

I am a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

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