When I traveled to Havana, I decided to pay homage to the 1950s vibe of this colorful city with 1950s fashion. 1950s fashion had two main standouts – One was the pencil skirt, the other was the tiny waist dress with a full skirt.

Picture shows me(Pari) posing in a white Tommy Hilfiger dress and a 1940s  style straw hat
1950s fashion – Tommy Hilfiger White dress teamed with a 1940s straw hat.

In the 30 degree heat, there is no way I was wearing a tight-fitting pencil skirt! Instead, I chose a white Tommy Hilfiger dress, which had hints of the classic 1950s cinched waist appearance. I deliberately chose a white dress so that the dress fitted in harmoniously with the colorful buildings of Old Havana. I paired this dress with a 1940s style straw hat which provided much-needed shade from the sun along with enhancing the classic feel of the dress. The belt which came with the dress helped to highlight my waist and giving an illusion of a slim waist.

Picture shows me (Pari) wearing a 1940s style polka-dotted top.
1940s polka dotted top standouts well against the blue water.

For the ride to view the corals in a submarine-type boat followed by a tour of the Bellamar caves, I chose to go with my faithful jeans. The walk in the cave demanded comfortable shoes and outfit. However, I wanted to stick to my 1940-1950s fashion. So, I chose a brightly colored polka dot top with a White Swatch watch and the straw hat from the day before coupled with Tahari Sunglasses. We had to walk a lot inside the caves so I opted for my super comfortable Ecco shoes. I am a fan of Ecco shoes because of the way the smooth interiors hug my feet.

Picture shows me (Pari) exploring bellamar caves in comfortable jeans, polka dot top and Ecco shoes
Exploring Bellamar Caves in comfortable jeans, polka dot top and ecco shoes

Shop 1950s Women’s Fashion

Want to know more about Havana? Check my posts : Old Havana Cuba: A Walking Tour Of The Four Plazas and Cuba Cars: 9 Cool Pictures of These Classic Beauties

Disclaimer: Some items shown here are not an exact match but are a close match to the outfit shown in the pictures. These links are affiliate links. This means I receive a small commission, at no extra cost to you, if you buy them.


  1. Great post! I would love to visit Old Havana – it looks so stunning. Your style is beautiful too. Love the pictures you took. It looks like you had an amazing time! Thanks for sharing!

    • Pari Reply

      Thank you Victoria. Old Havana is a beauty! I loved all the colorful building and the plazas over there. If you get a chance, you should definitely visit Cuba. I am sure you will love it !

    • Pari Reply

      Thank you, Kate . I have always loved 1950’s looks. This occasion was perfect to try it on.

    • Pari Reply

      Thank you Katie. I am glad you like it. I wish 1950’s fashion makes a comeback soon.

  2. Absolutely love the photos! I keep seeing articles about Havana and it is making me want to travel there. Also love the Cave. It made me think of It’s a Small World at Disneyland, but more rustic! Thanks for sharing.

    • Pari Reply

      Thank you Jenny. Old Havana is a beautiful place no doubt. You should go if you get a chance. The caves were also beautiful. Most of my photos couldn’t cover the actual beauty of the place because of poor lighting. Trust me it was amazing!

    • Pari Reply

      I agree, I love the 50’s look. I hope they make a come back. You should try and visit Old Havana next time. It’s so colorful and full of culture.

  3. That cave looks amazing and your fashion is spot on! I think I will have to add Havana and the Bellamar Caves to my places to see someday. Thanks for sharing.

    • Pari Reply

      Thank you Joanna. Havana, specially Old Havana, is amazing and worth a visit. I am planning to visit again next year:)

  4. I am dying to go to Cuba. I love that it’s stuck in the past! Your trip looks awesome!

    • Pari Reply

      Yes. I loved the lost in time vibe of Cuba. All those colorful classic cars were so amazing. I am planning to visit again. I haven’t had my fill of Cuba yet!

  5. Havana looks incredible! I’d so love to visit! I love the old, traditional and classic look. These outfit ideas are perfect for the scenery — love the polka dot dress with sleeves!

    • Pari Reply

      Thank you Leigh. Havana is one of the most colorful cities I have visited!I would love to visit again. The polka dress with sleeves was my favourite too. Wish I could afford it ;D.

    • Pari Reply

      Thank you Rica. I am glad you love Havana. I have added videos of Old Havana walking tour of Havana if you are interested. If you get a chance, you should visit. I highly recommend it.

    • Pari Reply

      Thank you. After the resort life (and huge portions of deserts) for a week in Cuba I have difficulty getting back into it ;D

  6. Love how you described the unique looks! Looks like an awesome trip with some style thrown in the mix. The 1950s look is a great idea!

    • Pari Reply

      Thank you so much, Anissa! It was so much fun going retro for this trip.

  7. Zoe Jackson Reply

    I love 1950s fashion, it is beautiful and your outfits are amazing. Great post!

    • Pari Reply

      Thank you for the lovely comment. I hope you come back for more ๐Ÿ™‚

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