Wooden Key West Sign | shepackslite.com

What To Wear: How To Dress on Your Key West Vacation (2022)

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If you have a Florida trip planned and are wondering what to wear in Key West, I am jealous! Key West is an excellent retreat from the cold winter weather. It’s also a great option when you’re itching to travel but aren’t interested in an international destination. For a tropical vacation within the United States, look at Key West for your next getaway. Keep reading to find out what should be on your packing list for your Key West vacation. 

Tips for What to Wear in Key West

Dress for the weather.

Key West beaches are relatively warm all year. You probably won’t need to pack more than a light sweater no matter what time of year you decide to visit. In the winter months, high temperatures range from the mid-70s to the low 80s. The summers in the Florida Keys are much warmer, with average highs around 90 degrees and average lows only around 80 degrees. 

Pelican on a Key West Dock | shepackslite.com

Of course, I always recommend checking the weather forecast ahead of time to make sure that you’re dressed appropriately for the weather. It’s likely that you won’t need more than a few lightweight layers for the early mornings and late evenings when the weather can be a bit more breezy. Otherwise, during the day you should be comfortable in a sundress or a pair of shorts and a tank top or sleeveless shirt.

Going to Key West Soon? You can check the weather forecast here!

In any case, you should always check the weather before you travel. For Florida and the Keys it is especially more so if you plan to travel during the late summer and early fall. That’s when tropical storms and hurricanes are more likely to pop up in the Atlantic. If you’re traveling a long way, you don’t want to arrive in Key West to find nasty weather. Keep that in mind both when you’re scheduling your vacation and when you’re getting ready to leave!

Be prepared for the beach. 

One thing you don’t want to forget for your Florida Keys vacation is a few swimsuits. I know, it seems silly to mention this for a destination like Key West. Some people get so caught up in their other outfits that they totally forget beachwear. If you’re planning on being near the water for most of the day, you’ll be totally fine wearing a cute coverup if you decide to take a walk through town or stop for some lunch somewhere. Beach in Key West | shepackslite.com

It’s also a good idea to have some kind of beach blanket with you for beach vacations. If you’re trying to pack light, you may not have room for a big bulky beach blanket, but if you find yourself with a little extra room, it’s a good thing to have. You can often find towels and blankets at a local grocery store or drug store, but in beach towns, they may be more expensive than they are at home. 

Some other essential items that you should have for the beach, especially if you’re traveling with the whole family, are a cooler bag, reef-safe sunscreen, and water shoes. Many sunscreen manufacturers will advertise that their sunscreen is reef safe these days, so if you have a choice, be sure to pick one that will help preserve the coral reefs. 

What to wear in Key West? Keep it casual. 

As the southernmost city in the United States, Key West gives a laid-back Caribbean vibe that you normally can’t find anywhere else in the country. With that, you can expect a more casual dress code than other vacation destinations. It’s not uncommon to see people walking around wearing a swim suit and a coverup. 

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Keeping it casual not only goes for clothing, but also the shoes that you bring. If you’re planning on spending a lot of time at the beach or pool, there’s no need to pack any fancy or uncomfortable shoes. Flat sandals are a great option for anything you’ll be doing in Key West. 

Pack some dressier clothes for the evenings. 

One of the best things about Key West is the relaxed atmosphere that it provides. However, if you’re in town for any special occasions like anniversaries or birthdays, you may want to get a little more dressed up in the evenings. The live music and restaurants on Duval Street are pretty laid-back, just like the rest of this beautiful place. Given the casual atmostpher so wear whatever makes you feel comfortable and confident. 

Duval Street Sign | shepackslite.com

One of the things I always recommend when packing light is using a travel capsule wardrobe. You’ll mix and match different items or wear the same item more than once. The good news is that you can dress an item up or down with just a few simple changes. For example, the sundress that you brought for the beach can be made a little more dressy! Just throw on a few pieces of jewelery and wear some nicer sandals. This way, you won’t have to use up extra room in your suitcase by packing a dedicated outfit for every dinner you have planned. 

Remember your other essentials.

Besides clothing, there are a few other essential items that you should have for your vacation to Key West. For travel days, be sure you have plenty of face masks, whether they be disposable or not. If the place you’re staying has a pool, a bathing suit also shouldn’t be the only thing on your mind. Chlorine can really dry out your hair and skin, so pack some conditioning hair treatments and lotion to help you replenish your dry skin and hair after pool days. 

Other personal items that should be on your list are sunglasses, a hat, contact lenses, and any other small toiletries that you won’t be able to purchase at your destination. When you’re in a new town, you can usually find most things that you’ve forgotten at a local drug store, but those things can quickly add up. Especially in a place that’s a popular vacation destination, it’s better to be prepared when you get there. 

FAQ: What to wear in Key West

If you still have lingering questions about what should make it on your Key West packing list, keep reading to make sure you’re fully prepared for your next beach vacation. 

What do you wear on a night in Key West?

Like I mentioned earlier, a sundress with some strappy sandals is totally appropriate for a dinner date in Key West. The unofficial dress code in Key West is very casual, so you shouldn’t worry about trying to fit those high heels in your suitcase. If you want to dress it down even more, go for it! A nicer pair of shorts or jeans won’t make you feel out of place either. 

What do people wear in Key West in the winter?

Key West is still much warmer than other places in the United States in the winter, but colder than it is the rest of the year in Florida. You might not think to pack jeans and a windbreaker when you’re traveling to a beach town. It’s a good idea to have them just so you’re prepared. Early mornings and late nights can get chilly and nothing spoils a vacation day like being cold and miserable. 

What should I pack for 4 days in Florida?

No matter what season you’re traveling to Key West, it’s important to pack layers. In the summer, you might need to shed layers in order to cool down, whereas in the winter, you might need to add some. As long as you stick with the basics in my travel capsule wardrobe, you’ll be well equipped for any trip. 

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