What to Wear in Cuba

by Brenna Holeman



These “what to wear” posts are some of my favourite to put together – as much as I love fashion in London, there’s something about the clothes I wear when I travel. As mentioned in previous posts, I love to mix my clothes from home with pieces I pick up on the road, whether that’s clothing, jewellery, bags, or shoes. I often form a sentimental attachment to the clothes I wear when I travel; there’s no way I’ll ever get rid of the alpaca jumper I bought in Peru, or the colourful scarves from India, or the wooden beads I bought in Havana.

Here, then, is what to wear in Cuba. Please note that this post includes some affiliate links!


I went to Cuba in 2012 with my best friend Rikki; we spent a week in Havana, with a day trip to Varadero. It was a fantastic week, and a fascinating country, one with a lot of beauty and a lot of history. We spent most of our time walking around Havana, taking it all in, occasionally stopping to people-watch or try a rum cocktail or two. As we went in March, the weather was absolutely glorious, with lots of sunshine and hot temperatures.

Cuba’s peak tourist months are mid-December to mid-March, but really, Cuba’s weather is fairly tropical all year round. November to April is the dry season, and it can also get a bit cool at night, whereas the summer months will be a bit hotter (and much more humid) with a greater chance of rain. Just things to keep in mind when you’re packing!


what-to-wear-in-cuba-13what-to-wear-in-cuba-4Not sure if that high-low thing is still happening (it isn’t) but this was my favourite dress in 2012, so it’s making the list

1. Dresses/skirts

If you’ve been following this blog for a while, you’ll know that I am a huge fan of skirts and dresses when I travel. I find them super comfortable, fashionable, and fun. In Cuba, I wore dresses in either white or red – I guess my Canadian patriotism was really on display – but I own similar dresses in lots of bright colours. Again, if you’re in Cuba, you’ll most likely be experiencing hot, sunny days, so it’s important to stay cool (and to embrace the colourful vibe of Cuba itself… I was obsessed with those exteriors). Obviously, if you don’t wear dresses or skirts, I’d recommend bringing shorts (see below) or light trousers. I’m also currently digging wide-legged culottes (never thought I’d say that out loud) so I’d bring a pair or two of those in lieu of a skirt.

Unlike my time in India, for example, I felt comfortable baring my shoulders and/or my legs. You’ll see local women in Cuba doing the same, so I felt it was appropriate.

Examples of dresses I would pack for a trip to Cuba include this one, because it is lightweight and will keep you cool while still covering your legs. I’m also a huge fan of this dress, because you can dress it up or down; I personally belt this one. Finally, I am all about the drama of this caftan; it would look amazing against all of the colourful houses in Cuba!



2. Shorts

Rikki, the most stylish person I know, brought an amazing collection of shorts with her to Cuba. They were perfect for walking around the city – they kept her cool, and they looked cool. I know that Rikki will be sad that I posted that first photo because those shorts were unfortunately ruined shortly after this trip… RIP incredible vintage sailor shorts.


3. Tank tops/t-shirts

While I brought mostly dresses to Cuba, Rikki brought an assortment of light t-shirts and tank tops with her to mix and match with her shorts and skirts.


4. Sandals/shoes

Yeah, I’m just going to go ahead and point out those bandages on my feet, because I stupidly did not break those bad boys in before deciding to parade around Havana in them. I mean, they looked nice, but… don’t do as I did, and make sure to bring at least one pair of very comfortable walking shoes or sandals. On the other days, I wore simple flat sandals or open-toed flats, and as per usual I almost always pack a pair of Keds for comfort (and… kinda cute style? I don’t know, are Keds still cute? I digress). If you are spending time on the beach, or your hotel has a pool, I would also recommend bringing a pair of flip flops.

Most of Havana (and I imagine the other cities) have often uneven sidewalks and/or cobblestones, so I wouldn’t recommend bringing shoes with a high heel.



5. Denim jacket / long layers

As mentioned above, Cuba can get a little bit chilly at night in the winter months. I would suggest bringing a denim jacket (my go-to jacket for any country, really) and a long-sleeved cardigan if you’ll be travelling in the cooler months. I also brought a kimono, but let’s be honest… I brought that to look cool, not to keep warm.



6. Handbag

As soon as I walked into our hotel room, the strap of my handbag broke. Not good. Thankfully, there are quite a few tourist shops and markets in Havana, so I was able to purchase the leather bag I’m wearing in all of these photos for about $20. It ended up being the perfect size for everything I needed, and I thought it was a great souvenir.

Whatever you decide to bring or wear, I’d make sure it is comfortable, roomy, and that it has a strap long enough to loop around your body. I felt perfectly safe in Havana, but I find that having a handbag that loops over your body means you can relax a bit more, have both hands free, etc.


7. Bathing suit

While our trip was primarily to Havana, we did spend a day on the beach in Varadero, so we packed our bikinis. If you’re going on a beach holiday, with many days spent by the water, I’d recommend bringing two bathing suits if possible – nobody likes putting on a wet bathing suit, and you never know what might happen to one (you lose it, it rips, etc). Make sure to pack one of them in your carry-on luggage, just in case your airline loses your hold luggage!


8. Beach cover-up

Whenever I know I’ll be on the beach or near a pool, I always bring a light dress or beach cover-up. I almost always bring a sarong as well, which can come in really handy as a wrap, towel, scarf, pillow case, and so on.


9. Hat

As mentioned, it will most likely be hot and sunny when you’re in Cuba, so having a hat to protect your head and face from the sun is great.

OK, but yes, let’s just talk about this Shar Pei puppy for a minute, because he’s kind of the reason I wrote this whole post. Look at his face!!


10. Sunglasses

You got it – it’s sunny in Cuba. I think my sunglasses kind of scream “It’s 2012 and I bought these at Forever 21 for $3.99” but hey, they did the trick.


11. Lipstick/Makeup

I never shy away from wearing makeup when I travel – even in really hot countries I’ll slap on some lipstick and mascara. As I’ve struggled with minor acne my whole life, I often don’t feel comfortable without a bit of makeup on, and if I wear it while I’m at home, why not wear it while I travel? Rikki and I both wore really bright, fun lipstick colours in Cuba.

By the way, in order to make my eye makeup stay, I swear by this eyeshadow primer. I hate to over-exaggerate and say it changed my life, but it changed my life. I can put on eyeshadow and/or eyeliner in the morning and it doesn’t move… all day. Even in hot, humid climates. My sister turned me on to this stuff a few years ago and I now wear it every single day. Also – waterproof mascara in hot climates.

I’m going to write a post about the makeup I bring when I travel soon… hint… it’s all cheap, drugstore stuff (minus that eyeshadow primer) because, unlike with clothing or jewellery, I personally can’t justify spending £30 on a mascara when I just bought flights to Italy for £24. I’d rather have the flights, but that’s just me.



12. Jewellery

It’s no secret that I’m utterly obsessed with jewellery… I even recommend it as one of the best and the cheapest souvenirs to buy when you travel. While I brought some of my own to Cuba, I ended up buying tons of really fun, cheap strands of beads (pretty much everything I’m wearing in this post). I always try to buy something local, no matter where I go… if you can, try to find shops or market stalls selling products that are definitely made in the country itself, not imported. It’s a way to support the place you’re in and take away a nice souvenir at the same time.

By the way, Rikki is equally as obsessed with jewellery… she even makes it, and she’s damn good at it. Her stuff is some of the most beautiful I’ve ever seen, and I wear something of hers almost every single day. Check out her Instagram as well as her Etsy shop.



So, there you have it… what to wear in Cuba. As Rikki and I were only on holiday there for one week, and checked a bag, we probably went a bit overboard with the outfits; I think we had a change of clothes for every day we were there (and then some). I think a very reasonable packing list for Cuba would look like this:

-3-5 dresses (or *cough* 10, if you’re like me)

-2-3 pairs of shorts or skirts

-5 tank tops/t-shirts

-2 bathing suits

-1 beach cover up


-handbag or backpack

-shoes: one pair of flip flops, one pair of runners, 2 pairs of comfortable flats/sandals

-one denim jacket or long-sleeved cardigan for nighttime

-fun accessories (i.e. red lipstick, jewellery, etc)

Of course, if you are only taking carry-on, you’d probably take a bit less, although I find that summer clothes like this tend to fold down quite small. If you don’t wear dresses or skirts, obviously bringing a few more shorts or light trousers would work, although I think it would probably be too warm to wear jeans during most months.

Also, this list is really only for those going on a more relaxing holiday, one that includes beaches and cities. If you are planning to do any sports (hiking, for example), I’d obviously recommend bringing the appropriate clothing and hiking shoes.

In either case, don’t forget to pack suncream and bug spray!



Have you been to Cuba? What does your wardrobe consist of when you travel?

If you’re interested, here’s another article I wrote about feeling fashionable while travelling (with photos from Cuba). Additionally, you can check out what to wear in Indiawhat to wear in Thailandwhat to wear in Nepalwhat to wear in Bhutanwhat to wear in Russia, and what to wear in Colombia.

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Korii September 28, 2016 - 1:41 pm

All these photos look amazing and I love your dresses – you have a fantastic sense of style! I am now even more inspired to hurry up and get to Cuba!

I laughed when I got to the part in your packing list where you confess to your tendency to pack 10 dresses – I am the exact same. My friends and I travelled around Europe last year and they couldn’t get over all the different dresses I’d wear each day – in retrospect, packing so many dresses was a terrible idea once it reached the end of August and we had gotten into Amsterdam!

Brenna Holeman September 28, 2016 - 6:02 pm

Thank you very much, Korii! Cuba is a really fantastic (and fascinating) place to visit. And don’t worry, I always overpack… I’ll just never learn! Thanks for your comment. 🙂

Katie September 28, 2016 - 1:46 pm

Aw, you always look super cute! I’m going to NYC next weekend with a girlfriend from the Women in Travel Summit and she always looks so put-together, too. I’m going to be freaking out about packing for this one. 🙂

Brenna Holeman September 28, 2016 - 6:01 pm

Thank you Katie! That’s very nice of you to say. I’m sure you’ll look fantastic. 😀

Christine September 28, 2016 - 3:21 pm

I love both your outfits! I always overpack when I go to Cuba because I can’t decide what to pack. I end up bringing bikini’s for every day that I’m there. Terrible!

Such good tip about packing lots of sunscreen and bug spray. I ran out of sunscreen once and purchasing it at the resort store was expensive. I pack at least 2 now when I go there.

Brenna Holeman September 28, 2016 - 6:00 pm

Yes, I’ve made that mistake with sunscreen before, too! And hey – if you’re willing to carry your suitcase, no harm in bringing a few extra bikinis. 😉

Melissa September 28, 2016 - 3:34 pm

Love these posts… Is a travel fashion blog a thing yet, because you could do one!

Brenna Holeman September 28, 2016 - 6:00 pm

I think there are definitely a few out there… mostly fashion bloggers who now travel, I believe. I do want to redesign the blog so that I have a section for fashion as I love to buy local clothing and integrate it into my wardrobe… stay tuned! And thanks 😀

Elina September 28, 2016 - 9:31 pm

Man, these posts are great! Although now you’ve got me all worked up about Cuba again, it’s so high up on my list and I’ve been dreaming about it for ages… Btw, did you think clothes and jewellery and stuff cost a lot there? Nothing’s probably gonna beat Asian prices but surely Cuba must be cheaper than, say, Europe.

Oh, and speaking of make up – I swear by the semi permanent eyeliner by Seventeen, you get it at Booths for like 5 pounds and it does not smudge at all even in hot climates. I sound like a total advertisement but that eyeliner is the best thing I have ever bought 😀

Brenna Holeman September 29, 2016 - 1:23 am

I didn’t buy any clothes there, so can’t comment on that, but the jewellery I bought was all quite cheap. And yes, Cuba is amazing, I hope you get there soon!

Sounds like a great eyeliner… I’m all about the cheap makeup 😀

Ella September 29, 2016 - 7:29 pm

I love your What to Wear posts because you seem to embody the nature of the culture you’re visiting with your clothes. Which I think is very cool 🙂 I don’t consider myself to be into fashion or a stylish person at all, but I really like seeing what you wear while travelling. Maybe it’s something that I could have a little fun with in the future, especially if I was somewhere as colorful and vibrant like Cuba.

P.S. That puppy is so cute!!!

Brenna Holeman October 2, 2016 - 1:38 pm

Thank you very much, Ella, I really appreciate that! I often can’t help but be inspired by what I see around me.

Zalie November 8, 2016 - 8:26 pm

I always love your what to wear/pack posts! No matter where you are, you always look amazing!! xo

Brenna Holeman November 11, 2016 - 2:18 am

Thank you so much, sister xoxo

Em January 4, 2017 - 8:07 am

So helpful to read for my trip next week! I’ll definitely be using it packing guide ☺…Also is that beach in your pictures in Havana or veradero?? How could I get there? I’m staying in Havana but really want to go to a beach like the one in your pictures for at least a daytrip!

Brenna Holeman January 4, 2017 - 4:27 pm

That beach is Varadero, which is quite easy to get to from Havana. I did it on a day trip, simply taking the bus. It’s only about two hours 🙂

Mo January 13, 2017 - 3:53 am

I know I’m really behind the times with reading this, but I just wanted to give you a shout-out! Life got too busy for me to keep up with blogs for the last few months, but I love yours so much that I couldn’t not read the ones I’d missed! This one was such fun, with such great photos!

Brenna Holeman January 13, 2017 - 3:13 pm

Aw, thank you so much, Mo! I really appreciate you taking the time to read my blog posts. 🙂

Kelsey March 13, 2017 - 2:32 am

I’ve creeped through your posts on Morocco multiple times, partly because when I read about “The Loveliest City on Earth”, I realized that one day I would have to travel to Morocco. That time has come, and I will be flying to Morocco in April. However, I haven’t the faintest idea of what I could wear. I dislike sleeves, but out of respect I will be acquiring some tops with sleeves. I know it’s been a while since you last posted about Morocco, there weren’t too many photos of you, so I was wondering if you could share any pointers.

As well, I was wondering if you have any insight as to whether or not a shirt with the shoulders cut out would be considered inappropriate.

Thank you for your brilliant posts!

Marisa January 28, 2018 - 12:37 am

Great ideas for some cute outfits to wear in Cuba! Looks like an amazing girls trip you guys had and definitely makes me want to do a fun trip with the girls soon too!

Brenna Holeman February 1, 2018 - 9:03 pm

I hope you get there soon! 🙂

Cindy Knul March 12, 2018 - 4:37 am

Great suggestions! Going to Cuba in April. Love your humorous style of writing.

Brenna Holeman March 12, 2018 - 4:35 pm

Thank you, Cindy! I hope you have lots of fun 🙂

gloria March 8, 2020 - 5:49 pm

so glad I found this article. planning on going to Cuba in April. I wasn’t sure what to pack.
Also, did you travel with a group or on your own?


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