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What to Wear in Key West

Key West is one of those places you visit and you feel at home, immediately. Why? It’s more than the Island vibe, it’s the people, the food, the drinks, and its casual approach to life. Which begs the question… What to wear in Key West?

Remember when I said it’s casual? Keep that as your packing theme. Most places accept you in flip-flops, shorts, and a shirt. But, I get it, sometimes we really, really want to wear our cute sundress and strappy sandals. Go ahead, pack those too, but don’t go crazy. You will get caught up in the casual atmosphere of the Island and most of what you pack … well, you know the story, probably won’t get worn.

But, seriously, let’s look at a must-have list. I try to make a game out of packing. I don’t like to wait for my luggage when we land at Key West International Airport (who does?), so I only do carry on. This is where the game part comes into play… how can I take what I want, but get it to fit into carry-on luggage. My must-pack list always includes:

  • Flip flops
  • Tank tops – especially in the summer months
  • Bathing suit, or two. I always spend time by the pool or at the beach
  • Personal items; like face wash, make-up, lotion, toothbrush… you get the idea
  • Light sweater or pullover. At night, or out on a sunset cruise, the wind may be a bit chilly, especially during the winter months.
  • Comfy walking shoes
  • Shorts
  • Sleeveless shirts, a bit more dressy than a plain tank top, but still really casual

Do you like to create a packing list? Me too! Check out these really cool ideas for your Bullet Journal.

What Will You Do?

Planning to visit one of the Key West beaches while in Key West, maybe add a pair of water shoes. The beaches, especially at Fort Zach can be rocky. Need a beach bag? I use my personal item (the piece of luggage that fits under the seat) as my beach bag. Double duty for sure.

Imagine getting up and going for a walk down Duval Street, before all of the stores open and the crowds start to gather. That’s why I pack comfy walking shoes, After I explore I grab a cup of coffee from the Cuban Coffee Queen and walk over to Mallory Square to enjoy my morning caffeine.

As you can see, I pack based on what I am going to do while in Key West, I find it the best way to make sure I am prepared. Heading out on a snorkel trip to see amazing blue waters and the coral reef? Don’t worry about sunscreen, most tour companies offer free reef-safe sunscreen to use while onboard. Just ask, if they don’t, there are a lot of places on Island to pick up sunscreen.

Of course, should I forget anything, I can ALWAYS go shopping. Maybe I need a new dress or a really cool sweatshirt… then I will hit up any of the amazing shops found on the Island. Especially if I need a new pair of flat sandals, I will head over to Kino’s. Made right in Key West, it’s the perfect way to bring a piece of Key West home. But, most of the time, no matter what we are planning to do, I can assume a casual dress code.

Maybe you are taking the Ferry to the Dry Tortugas National Park. Grab your beach bag and plan to have fun. Even on this trip, what to bring is very limited. and casual Here’s what the Yankee Freedom suggests you bring.

Want to escape some of the summer heat? The Ernest Hemingway Home has air conditioning. A tour guide will take you through the home and you will get to meet the famous six-toed cats. Even here the dress code is casual and it’s a way to spend an afternoon out of the summer heat.

Other ideas?

  • Get your picture taken at the Southernmost Point
  • Go on a sunset sail – maybe even with a live band!
  • Take the Trolley over to New Town
  • Check out the sunset celebration at Mallory Square and see the street performers

More Ideas on What to Do While in Key West

Plan to do a lot of walking. Key West is a very walkable city, actually, it’s encouraged. No need to rent a car. A great pair of comfortable walking shoes will get you where you need to go. Feet get tired? Then hop on the Duval Loop or grab an Uber.

What About the Weather?

Depending on the time of year, you may need more layers. During the very warm summer months, I usually plan on changing my clothes a few times during the day. A fresh set of clothes for evening activities always makes me feel much better… refreshed. In the cooler winter months, I may choose to wear shorts during the day but change into jeans and a pullover for the evening. Just check on the expected weather before you pack.

The average highs in the summer are in the low 90’s but remember it’s Key West and the humidity may make it feel like 100 degrees. While in the winter months, when there is lower humidity, the average highs are in the upper 70’s, but the average lows could be in the 60’s. But, I must say, when it’s snowing up North this Southernmost City in the United States calls my name… daily. Who doesn’t wish they were enjoying palm trees and a warm tropical climate when looking at snow?

Where will you Eat?

Of course, one of the best things about Key West is the food. It’s a foodie heaven for sure. In Old Town, there are so many choices. I think the best places offer the casual vibe we all love. Put on your comfy shoes and head out to explore. Blue Heaven for brunch followed by a cocktail and live music at Sloppy Joe’s no need to dress up.

I love to head over to the grocery store, grab a few snacks and enjoy them back at the room. After a day of walking around, it’s really nice to sit, relax with a great glass of wine and a yummy snack. Maybe grab a takeout pizza from Onlywood and call it dinner!

Other Thoughts…

Coming to Key West to enjoy one of its many festivals? Maybe Conch Republic Days or even Fantasy Fest? If you are planning to attend one of the events with these festivals, there may be a different dress code, but in general, it’s usually casual. Should you arrive and find out there’s a festival happening, trust me, you will be able to find what you need on Island.

Key West is a great place to enjoy all that the island life can offer. Live music, great food, cocktails, and so many activities. As you can see, I am very smitten with Key West. It had my heart from my very first visit.

My best tip? When packing for your Florida Keys vacation, keep it simple. Less is always best.

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