BeachesWhat To Wear In Key West: Outfit Ideas
what to wear in Key West

What To Wear In Key West: Outfit Ideas

What to wear in Key West?- is the first question when you book your Keys’ vacation.

What will you be wearing when you travel to Key West?

Walk Duval street and have mojitos in the oldest restaurant? Getting sugar-high on the best Key Lime cake in the world?
Take the tropical paradise photos for your Instagram?
And what should you throw in your beach bag when you’re taking the famous Key West sunset boat tour?

The first thing that strikes you upon arriving to the Keys is… how does it get so HUMID!? Key West climate averages 30 Celcius year-round. Late spring, summer, and early autumn are not ideal for traveling. Even with the breeze you catch everywhere in Kew West; it’s still pretty brutal.

What to pack for Key West’s Caribbean vibe and tropical heat? 

The tropical packing list should follow what I call the PPH rule: Practical – Picture-perfect-Heat resistant. Easier said than done, isn’t it? 

So let’s get into the details of what to wear on Key West, plus see some Key West outfit ideas.

Loose-Fitting Maxi Dress

The number one clothing item that delivers extreme breathability and is perfect for photos is the maxi dress.
Choose loose-fitting styles (you’ll be glad you did after the Key’s world-famous lobster rolls & Key Lime Pie!) Loose-fitting maxi dresses look great in photos even if you opt for neutral colors. They just catch the wind so beautifully!

Go for a vibrant dress and mix it with an animal print accessory for a fun and unique look.


Crochet is having a moment this summer, and I couldn’t be more thrilled. There’s something about the handcrafted look that just feels quintessentially summery, whether it’s a tassel-adorned top, a pair of macramé earrings, or a crochet-trimmed swimsuit. To keep your take on the trend modern rather than full-on bohemian, try paring back an intricately knitted dress with some sculptural jewelry, or grab a woven bag to carry with your head-to-toe bohemian look. I strongly reccomend having at least one crochet accent for the sunny season.

Swim suit

A swimsuit is always the first item on my packing list for any beach vacation. You want something that will be comfortable enough to swim in, but also look good in any photos you’ll take. I used to think that swimsuits were only meant to be worn for the ‘gram. I would pack the cutest swimsuits, but they were always so uncomfortable and impractical. I quickly learned my lesson after a few too many swimsuit malfunctions.

For your trip to Florida Keys, try to pack swimsuits that are both cute and functional. For example, a mix of bikinis and one-pieces that are perfect for both swimming and taking photos. And don’t forget that bold floral or geometric prints are perfect for any occasion.

Fun, playful shorts

One of the things you are likely to be wearing in Key West for cuteness and comfort are shorts, especially if you are taking on sporty activities or renting a bike in Key West. Or going up the stairs to the top of the famous lighthouse.
Shorts and miniskirts are perfect for more quiet events.

What shoes to pack for Key West

When packing for a trip to Key West, keep in mind that you’ll be doing a lot of walking. Whether it’s bar hopping or museum hopping.

The best shoes for walking are comfortable and provide good support.

However, I’m a strong believer that there is no such thing as a perfect shoe for travel. Your feet will still likely become swollen and sore from all the walking and happy hour-ing no matter what shoes you wear.
Pack shoes that are stylish, weather appropriate and versatile :

Tan Sandals (leather)

Tan sandals are the most versatile shoes for tropical travel. More often than not, they are comfortable to sightsee all day. And a perfect addition for a flow dress on a night out. Unless you are a heel girl. In Key West, sandals are a must-have.

Choose a versatile pair that can be dressed up or down.


If you’re looking for something trendier, espadrilles are a great choice. They come in all different styles, colors, heat resistant and, well… they were invented for the warmer climates!


Finally, don’t forget to pack a pair of flip-flops es for the beach or pool.

Tips for swollen travel feet

When my feet start to swell on vacation, I have a few go-to tricks that help me get through the day.
Tip 1: Foot massage- you can find quick and inexpensive options in any travel destination. It really helps to reduce the swelling.
Tip 2: Warm bath. If a foot massage isn’t available, a warm bath at the end of the day does the trick.
Tip 3: Ice bucket. And if my feet are really swollen and painful, I’ll do an ice bath. I fill up a bucket with ice and water and soak my feet. It sounds torturous, but it really helps!
Tip 4: Shoe rotation. I just rotate the shoes I wear each day when traveling and walking a lot. I’ll wear sandals one day, flats the next, and sneakers the next. This way, I’m not putting pressure on one part of my foot for too long and causing further swelling.

Accessories to pack for Key West:

Hats, wraps, and silk scarves
Heat defense hides bad(or very humid) hair day, picture-perfect
-hide the humidity-affected hair is never pretty – but you can make it look better with a scarf. Use it as a bandana. Silk or any other natural fabric with the best.

Don’t forget that accessories are lightweight but add so much personality to your outfit! Basically, your Kew West packing list may consist of neutral-colored dresses and lots of fun sunglasses, scarves, and hats. No matter what you are going to wear in Key West, accessories will make it look better!
Accessories are super practical things to pack for any vacation. And fun raffia earrings and bags are perfect to wear them in Key West.


No vacation outfit is finished without the ideal jewelry pairings, and this rule definitely applies to dressing up on vacation.
Think raffia or any other natural material – it’s a better fit with the environment and not too precious in case you lose it. Plus, statement raffia earrings look fantastic in the photos!

Straw Hat

If you’re headed to Key West, a wide-brimmed sun hat is an essential item to pack. Not only will it protect you from the harmful rays of the sun, but it will also keep you cool and comfortable in the heat. First, it’s relatively inexpensive. Second, it can be worn for a day at the beach or boat. Third, it will also protect your face and neck from the sun’s rays. Fourth, it’s stylish and will make you look great in all your vacation photos.

The best hat to make your travel photos pop is a while straw hat! But loose ends straw hats look very chic too. If you can, try to go with natural straw.

What to pack for a Key West vacation – the sum up

So, what to wear in Key West to match Caribbean vibe and be comfortable?

You won’t need suits, ties or dresses in Key West, because it is a beach destination.

A woman’s Key West packing list :

  • shorts
  • t-shirts
  • comfortable shoes (flat sandals)
  • flip-flops
  • swimsuits

A man’s Key West packing list:

  • shorts
  • comfortable polo shirts or other t-shirts,
  • one or two Hawaiian shirts
  • comfortable shoes

Casual Caribbean vibe

In Key West, you will find a brilliant Caribbean vibe, so you have to prepare for a more casual dress code than in other vacation destinations. For the evening restaurants, with live music, dress a little bit up, but remember the atmosphere is relaxed, so you don’t need to worry about fancy clothes.

What to wear for dinner in Key West

Dinner dates in Key West call for strappy sandals and a sundress. You don’t have to worry about fitting those high heels in your suitcase in Key West because the unofficial dress code is very casual. Don’t be afraid to dress it down even more! You won’t feel out of place in a nice pair of shorts or jeans, either.

Looking for a perfect One Day Key West Itinerary? Check out this blog post.

I believe that you can travel the world without quitting your job. I believe that you can experience all the magic, the foodies and the cultures of the world while having a normal life. And, perhaps, two dogs. This is exactly what I’ve been doing for 15 years. This is exactly what my blog is about. Love, Lilia

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