Packing For Cuba: What We Wore

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If you follow me on IG (@shanachristine), you know that we recently returned from an amazing trip to Cuba.  I have so much more to say on that topic (hopefully next week??), but so many of you were asking for outfit / packing details that I wanted to crank this one out.

We visited Cuba at the end of March, which is technically considered their cold season, but…it was glorious.  Hot during the day, yet cool enough in the evenings to need a light jacket or sweater.  It did rain once, but blew in/out so quickly that the net result was wandering into the bar for one more mojito.  #twistmyarm

As I mentioned in the Kid’s Cuba Packing List article, we brought only carry-ons to avoid the long luggage line at the Havana airport.  Made extra tricky by the fact that one can’t easily run out for, say, forgotten sunscreen in Cuba.  Cuba is not a shopping destination (to put it mildly), so you’re more likely to do without rather than replace it.

A few things I learned:

  • In the off season, Cuba does get cool at night.  Especially when there’s a breeze.  (And when walking along the Malecon, there was always a breeze.)
  • Cubans have style.  It’s more of a Miami vibe than an East-Coast hipster vibe, but grown men do not seem to wear shorts at night, and the women dress sexy.
  • On that note….I thought, for a hot second, that Cuba might be conservatively dressed.  HELLS NO.  Even the Cuban TSA agents wore short, tight skirts with fishnet tights.  I am not making this up.  It was amazing.
  • Old Havana has lots of cobblestones.  I didn’t bother with heels once the entire trip.

Here’s what worked for me:

On The Plane

 

It was 28 degrees in Philly the morning we left, so I needed something warm(ish), but with layers that I could easily shed once we hit Cuba. Needing to pack light (aka carry-on), I also wanted the jacket to be cute enough to wear over dresses at night in Havana.  A bomber jacket with a shrunken fit was perfect.

Secondly, a comfy, cut-out bootie was perfect for the cold-to-warm travel.  I was warm enough in Philly, cool enough in Havana, and felt cute and stylish the whole way.  Seriously shout out to these boots – I’ve worn them in four countries now and they’re still going strong.

 

Travel Outfit Details

top: Anthropologie Crocheted & Cropped Pullover  (size S for reference)

jacket: Madewell Satin Bomber Jacket (size XXS for reference)

jeans: AG ‘The Legging’ Ankle Jean in ’11 Year Swap Meet’ (size 24 for reference)

bootsLucky Brand Bashina in ‘Sesame’ (almost sold out), but Lucky’s Kambry Bootie comes in a gorg ‘Warm Stone Suede’ and we swear it’s the exact same thing (and it’s darker than pictured online).

 

In Our Backpacks:

I listed the items that kids packed, here.  Below is a list of what Mike and I packed into our small, personal carry-ons.  For reference, I carried Rebecca Minkoff’s Medium Julian  (you can see it pictured – it’s the smaller one), and Mike carried ONA’s photographer backpack which is amazing.

  • iphone
  • wallet
  • all four passports
  • all four visas/plus our itinerary (more on this point later)
  • chargers
  • camera and lenses
  • kindles
  • laptop (accidentally left at home)
  • Travel and language guides.  We found these helpful:
  • one TSA quart bag (each):
    • Mike: shower stuff and toothpaste
    • Me: all toiletries and my makeup
    • Raines: this bugspray (2 bottles, each under 3 oz) and travel hand sanitizer
    • Pax: this sunscreen (4 bottles, each 3 oz – it was a tight fit, but worked)

 

 

 

Playa del Estes

We spent a day at Playa del Estes (the BEACH, yo), with an additional stop at Hemmingway’s estate.

Outfit Details

bikini: Mara Hoffman String Bikini Top, Mara Hoffman String Bikini Bottom also available on Amazon here and here

top: Apiece Apart Galisteo Chambray Swing Top  , XS for reference (I adore this company – started by two friends in NY.  Read more here.)

shorts: 3 x 1 Cutoff Shorts (size 24 for reference)

sandals: Salt Water Sandals in red

sunglassesSmoke x Mirrors Rocket 88 Sunglasses  but THESE Warby Parkers are dangerously close (and only $95 bucks)

beach towels: Dock & Bay Microfiber Beach Towel (and pouch!)

Vinales

One of the highlights of our trip was a gorgeous, fun-filled day in Vinales.  We visited a tobacco farm, walked around a local festival, went horseback riding, and explored some underground caves.  I mean…wow.

This outfit wasn’t *quite* the multi-purpose outfit I had hoped it would be.  Horseback riding wasn’t the most comfortable in shorty-short shorts and Saltwater sandals.  And it turns out I didn’t need the swimsuit.  I knew there were underground rivers to explore by boat, and since my boys have a knack for getting wet….I guess I just wanted to be extra prepared.

However, if you hit Vinales and Sorora in one day (we did not but it’s a pretty common pairing)….then I do believe there is a swimming hole involved.  In which case I would’ve been READY.

 

Outfit Details

One-Piece: Solid and Striped ‘The Anne Marie’ Striped Swimsuit 

Tank: Free People ‘Sand Dollar’ Tank (size xs)

Shorts3 x 1 Cutoff Shorts (size 24)

SandalsSalt Water Sandals in red

SunglassesSmoke x Mirrors Rocket 88 Sunglasses  or these similar Warby Parkers

Around Havana

We spent most of our trip wandering around Havana.  Comfy (but stylish) shoes, a few pretty dresses, and a warm topper for night is all I needed.  I also brought a cozy hoodie and sweatpants for late night Uno games on our balcony.

Outfit Details

yellow dress: Aijek Ann Broderie Pinafore Dress

sandalsSalt Water Sandals in red

bagRebecca Minkoff Medium Julian in ‘Khaki’

jacketMadewell Satin Bomber Jacket (size XXS for reference – I like the slightly shrunken fit, especially over dresses)

Outfit Details

dress: Fleur du Mal Mini Slip in Black  (size xs for reference)

sandals: Rebecca Minkoff ‘Georgina ‘Gladiator in Black

jacketMadewell Satin Bomber Jacket (size XXS for reference – I like the slightly shrunken fit, especially over dresses)

 

Outfit Details

top: Zadig and Voltaire Hilda tank (on sale: same tank with a small design, or pretty details)

skirt: FRAME ‘Le Color’ Denim Pencil Skirt (size 25 for reference)

sandalsRebecca Minkoff ‘Georgina ‘Gladiator in Black

sunglassesSmoke x Mirrors Rocket 88 Sunglasses  or these similar Warby Parkers

bagRebecca Minkoff Medium Julian in ‘Khaki’

 

Outfit Details

Sweatshirt: Find new season’s colors here or my ‘Max Orange’ here

SweatpantsNike ‘Gym Vintage’ Capris

 

Guy’s Packing List For Cuba

Guys are easy.  Mike basically wore tshirts, shorts, and espadrilles every day, and some version of this outfit at night:

shirt | pants | small camera bag

Also, we found these sweet swim trunks.  It’s a lot of man thigh, but I like that. 🙂

t-shirt | swim trunks

My Cuba Capsule Wardrobe

For ease of shopping (if you are so inclined), here’s everything mentioned above…..


 

Mike’s Cuba Capsule Wardrobe

Now off to happy hour.  We’ve got some Havana Club and cigars waiting.  Best. Souvenirs. Ever.

xo,

S

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About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and denim-underwear, always.

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15 Comments

  1. Christy Hartman on

    Is it my imagination or is that yellow dress bra friendly?!

    Also, at what ages did you start traveling with your boys? Mine are 3 and 5 and I look forward to it, but we just aren’t there yet.

    • I have a 3 and 6 year old we travel internationally every other year since my oldest was 1. It’s absolutely nothing like traveling without children but it’s not that different from planning a day out with small children, in my opinion. We really had to lower our expectations for what you can do, for example I love to just wonder around cities, my kids just can’t do that, but they do love to explore playgrounds (of course), so I always research playgrounds before traveling to a new city.

    • We went to Cuba when our children were 6 months and 4 years old and it was terrific. My daughter was still breast feeding which made it really easy and we just found the people there so accommodating and wonderful with children. We have also camped with them their whole lives.I think if you go to the right places (make sure they have good infrastructure and are kid friendly) and you keep your plans light and flexible, travel with little ones can be really fun. We also rent a cabin on a lake almost every summer with my sister and her kids: aunties, uncles, and cousins make travel even better than staying home: built in friends and we trade off on child care so we can each have a “date” while we are away.

  2. Are you sure your booties are the sesame color? The look like the brindle color (more of a taupey grey) to me. I ordered 5 different Lucky Brand perforated booties to try and ended up favoring the Bashina/brindle combination, although the sesame (more of a tan color) was a close second, and I am lusting after the Bartonn but it didn’t come in the color I want in my size. :(.

    FYI, The Kambry (this year’s Bashina) differs in that it has pinhole perforations instead of slits and, more importantly, it has an elasticized gore on the inside, so if you have a high instep or wider feet/ankles they will be easier to get on. On my skinny ankles they just looked floppy though, and i did prefer the slit perforations. So now we have matching shoes #notastalkeriswear

  3. So did you pack all of these clothes in the carry on? Because it seems like you’d have to wait at baggage claim anyway if not. It sounds like waiting at baggage claim was what you were trying to avoid.

    • I was thinking that too. That is a lot of stuff. Also, i NEVER EVER EVER wear anything that is not high rise. Not skirts, nor jeans, nor slacks. Have any suggestions for a Cuba wardrobe with less stuff, and high rise things?

  4. I love all your posts! So many cute outfits. Would you mind telling me how tall you are? I love those jeans and not sure if a 24 or 25 would be more appropriate… i kinda of straddle between both sizes… need a 24 1/2 LOL! We just booked our trip to Hawaii and all of these clothes are perfect for that trip too. Thank you!!! Always such great options. xoxo

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