One Swainky Couple: Strolling the Streets of Old San Juan

Friday, July 28, 2017

Strolling the Streets of Old San Juan

K: This was perhaps our favorite day of vacation. It was our first morning and after a short thunderstorm in the morning, Brandon and I prepared to tour the city of Old San Juan. With colorful houses lining the streets, ocean views, gorgeous flowers, and charming restaurants to cool off in, we felt like we could stay forever. If you've missed our last few posts, be sure and check out 7 Reasons Why You Should Go to Puerto Rico and our review of the Condado Vanderbilt

B: Our first morning in Puerto Rico was a blast. We started the day off right with a manatee sighting, following it with a lengthy stroll through the straight streets of Old San Juan. We loved that the streets and sidewalks were not crowded with pedestrians. Several residential streets contained no street signs, tourists, or automobiles, allowing our imaginations to wander towards what variety of languages were spoken, and what kind of people lived in the historic past of the large three and four storied dwellings.

On a lighter note, short sleeved pants and short sleeved shirts were a necessity for the duration of our stay. The almost daily rain storms sweeping across and past the island brought a healthy supply of humidity which only increased the already warm tropical ambient temperatures. Katherine and I both love polka-dots, and are willing to post them as much as possible to help bring their trendy days back.

K: Straw bags have been trending all season, but for me, some of them were just way too expensive to justify. I know that the trend will come and go, so I searched for a more affordable option on Etsy. I stumbled upon a cute little Etsy shop with a woman from China who was making the bags at a fraction of the price, but with a high quality feel. If you're still in need of a straw bag and want to partake in the trend, this bag is absolutely amazing. It's even lined and has a little drawstring at the top so that you can seal your items away. I carried it the entire trip and even took it down to the beach as our beach bag. 

On a separate note, this skirt...I saw it in Ann Taylor and was so disheartened when they didn't have my size. As I strolled through the store, I noticed that it was also in the petite section. I'm 5'5" and can occasionally get away with wearing petite, depending on the clothing item. This skirt ended up being a perfect fit and as we walked the streets, I found that I loved having it just a bit shorter so that it didn't drag the ground. This kept it from getting filthy and wet after the small rainstorm that blew in. The palm print is gorgeous and seemed to fit our surroundings perfectly. I've linked a few other maxi skirts below since they're such a great option for keeping cool in the summer heat. 

B: Puerto Rico is full of cats. They are literally all over Old San Juan. It just so happens that Katherine and myself are big fans of cats, and we found ourselves petting, picking up, and talking to nearly every cat we came across. Katherine could not help herself with this cute little kitty. She held it, named it, and proclaimed that we needed to take her back to our home. When Katherine came to her senses, she realized the baby kitty needed her mother, and we let the kitty happily carry on with kitty cat life.

 On Katherine: J. Crew bodysuitAnn Taylor skirt,  straw bag c/o, Dolce Vita sandals, Kendra Scott earrings

On Brandon: Nordstrom shirt (under $50), J. Crew shorts, Sperry shoes, Persol sunglasses


  1. The perfect looks for strolling the streets of Old San Juan! You guys look so cute and I love the palm print skirt on you! Have a great weekend!

    xo, Rachel
    A Blonde's Moment

  2. It looks absolutely gorgeous there and that palm print skirt is AMAZING! Happy Friday!!

    Rosy Outlook

  3. That skirt is so pretty! Looks like such a fun day!

    Taylor |

  4. Absolutely LOVE your outfit Katherine!! Perfect vacation look. And airy too-which I'm sure was necessary.

  5. This is SO lovely <3 And both your outfits look so good!

    Enclothed Cognition

  6. This looks so fun! I love your outfit, too! XO -

    Anna |

  7. Such great photos! I love the look of your outfits especially the skirt and basket bag! Have a lovely weekend.

    Gemma x

  8. I'm absolutely in love with your outfit! That skirt is just so perfect!


    Tamara -

  9. This trip looked amazing! I love this skirt and love that you found a kitty :)

  10. Love all your looks. Perfect beach bag babe! You’re flawless!
    Have a fabulous weekend ahead!
    Much love, Len

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  12. Ohmygod! These pictures are amazing! I am glad to have discovered your blog! You are so pretty and that is the cutest kitten ever! :) I am happy that you had a great time in Puerto Rico! Would love to visit that place someday! Have a lovely weekend! <3

  13. Okay your skirt and top could not be more perfect for vacation! LOVE! And I like how your outfits coordinate without matching. Sounds like such a fun day.

    Amy Ann
    Straight A Style

  14. Old San Juan is my favorite place of all!! Love the photos! You guys look great <3

    xoxo meli

  15. It looks like a nice and romantic stroll! I hope you enjoyed!

  16. Please stop! You guys are a beautiful couple. Love the outfits and the scenery. That kitten is pretty darn cute as well. I think my hubby and I need to plan a little trip!!

  17. Sounds like a great trip! You both are so cute! I love your palm print skirt!

    Doused in Pink

  18. Your outfit is a stunner! Love the print of the skirt and the off shoulder together!

    Jessica |

  19. You two look adorable! Love the photos!

    Have an awesome day!
    xx Kris

  20. So obsessed with your summery vacay outfit! Looks like such a great place too!

    Chow Down USA

  21. San Juan looks so beautiful! Im obsessed with your outfit too!

    <3 Shannon 
    Upbeat Soles