What to Wear in Naples Florida - Criss Crossing the USA (2024)

Welcome to the Ultimate Clothing Guide for Naples, FL, for the Entire Year!

I’ve been to Naples more times than I can count, and I always manage to find something new. Lately, I’ve been wandering with my boyfriend, and we’re blogging about our experiences. So if you want to find the best outfits to blend in, you just found the right place.

Look:

There are only two seasons in Naples, FL high summer and low summer. During high summer there’s a lot of rain. So no matter the month, it will be warm all year round, and sandals will be in fashion and comfortable.

Pick any month of the of the year and I have you covered. Let it be by season (yes, I’ve added spring, fall and winter next to the high and low summer) or by months I’ve managed to find the best outfits for you to look fabulous.

Scroll below and enjoy.

Show it to me already!

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What to Wear in Naples Florida - Criss Crossing the USA (1)

What to Wear in Naples Florida in Spring

I love Naples FL in the spring. For some this is the best weather all year round because it’s not too cold or too humid.

Plus if it’s spring, then the days are longer so you can enjoy the sun without the fear of getting sunburned.

Since the water isn’t too cold it might be perfect for a few daredevils. So having your typical beach attire like sandals, flip-flops, bathing suit, covers and such is an absolute must.

During the day wear casual all the way. I recommend getting this great Roxy Women’s Oceanside Pant paired with Hanes Crew Sweatshirt.

What to Wear in Naples Florida - Criss Crossing the USA (2)
What to Wear in Naples Florida - Criss Crossing the USA (3)

As for evening wear, you can choose from ECOWISH Deep V Neck Floral Leopard Dress or The Drop Women’s Britt Tiered Maxi Tent Dress.

What to Wear in Naples Florida - Criss Crossing the USA (4)
What to Wear in Naples Florida - Criss Crossing the USA (5)

What to wear in March

Brace yourself; you will need layered clothing for March in Naples. When the sun goes down it will get chilly fast.

So you need clothing both for the 70’s highs and the cold ’50s.

Best of all if you’re not going somewhere fancy casual all the way. Also bring a cardigan or one of my favorite Vegan Leather Motorcycle Jacket.

What to Wear in Naples Florida - Criss Crossing the USA (6)
What to Wear in Naples Florida - Criss Crossing the USA (7)

What to wear in April

April is the perfect month to visit Naples because it’s before the humidity jumps and the tourists rush in. Plus the prices are still low.

The weather is getting warmer so expect the temperatures to be in the 70-80s.

Loose and casual will make the day enjoyable. I highly recommend this Oiumov sundress or TARSE Women’s Capri with t-shirts.

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What to Wear in Naples Florida - Criss Crossing the USA (9)
What to Wear in Naples Florida - Criss Crossing the USA (10)

What to wear in May

During May the days are longer and warmer. If the weather is on the colder side then I advise getting some light layers because it won’t be cold in Naples.

It’s all about comfort and luckily there are only a handful of restaurants in Naples that require a formal dress code. If you’re not going there wear casual and comfy clothing.

Keep in mind that on the 1st of May Turtle Season begins.

The best clothes to wear would be light jeans like the Levi’s Women’s 721 High Rise and Women’s Lightweight Long-Sleeve V-Neck Tunic Sweater. Of course t-shirts and Short-Sleeve Woven Blouse

What to Wear in Naples Florida - Criss Crossing the USA (11)
What to Wear in Naples Florida - Criss Crossing the USA (12)
What to Wear in Naples Florida - Criss Crossing the USA (13)

What to Wear in Naples Florida in Summer

Enjoy the warmth of the sun and the ocean. Naples gets occupied by tourists during the summer months, so it’s a great place to make new friends.

Keep in mind that you will need 3 absolute essentials when you hit the region during the summer months. These are sunscreen, mosquito repellant and an umbrella. Besides being a warm month it’s quite humid with frequent rain clouds.

Since it’s the summer time of course you will hit the beach or the pool so make sure you pack multiple swimsuits. Here are my favorites BALEAF Women’s Athletic (once piece) and SPORLIKE Women High Waisted Swimsuit (two-piece) :

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What to Wear in Naples Florida - Criss Crossing the USA (15)

No swimsuit would be perfect without a cover-up (Jeasona Women’s Bathing Suit Cover-Up):

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What to wear in June

June in Naples is known for being hot and humid plus it’s the second month of the rainy season.

For the beach it’s easy sandals or flip-flops with a swimsuit picked from above including a cover-up.

If it’s rainy and you still want to see the city a short dress like (BELONGSCI Women Sweet and Cute Sleeveless Racerback) will do the trick

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Since it will be hot, go in tanks and short skirts or pants.

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What to Wear in Naples Florida - Criss Crossing the USA (19)
What to Wear in Naples Florida - Criss Crossing the USA (20)

What to wear in July

Now we’re cooking. July is quite hot plus it’s the middle of the rainy season so make sure you have a poncho packed and of course the umbrella will become handy.

As for clothing my favorite choice is flowy skirt let it be short or long (EXLURA Womens High Waist Swing Skirt or Relipop Floral Flared Short Skirt)

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What to Wear in Naples Florida - Criss Crossing the USA (22)

Also I recommend fast-drying shorts like the Little Donkey Andy Stretch Quick Dry Shorts and the LouKeith Tank Tops Casual Flowy Blouse.

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What to Wear in Naples Florida - Criss Crossing the USA (24)

What to wear in August

Is Summer done already? Well not quite yet. It’s your last chance to show off your fabulous summer clothes.

August is pretty similar to July it’s hot and damp. The rainy season will end soon, though.

Since it’s still summer, all the usual bathing suits, cover-ups and loose clothing can be worn. I will add to this list some cool T-shirts like Sunflower Summer T-Shirt or the ICTIVE Long Sleeve Loose Fit shirt to protect you from sunburns.

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What to Wear in Naples Florida in Fall

Is there a fall in Naples?

Well if there’s it’s a pretty short one. Basically there are 3 seasons in the fall that can’t be really felt.

The only difference would be that it’s not hot and it’s not that humid. It’s very closely followed by winter.

For warmer days I recommend a tunic dress Amoretu Tunic Dress V Neck Casual Loose Flowy or for colder days there’s the Imily Bela Cardigan Sweater.

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What to Wear in Naples Florida - Criss Crossing the USA (28)

What to wear in September

Before you start packing, make sure you check the weather report because hurricanes and tropical storms are frequent in these months.

If there’s nothing on the radar, then enjoy your stay in Naples. Even if the rest of the states are cooling down Naples is still hot and the water stays warm as well.

Yes, you can still pack your bathing suit and cover-ups yet here are some cool stuff to wear when you’re in town. I personally love Newchoice Tank Tops V Neck Sleeveless Shirts or Langwyqu Crewneck Sleeveless Tank Tops.

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What to Wear in Naples Florida - Criss Crossing the USA (30)

What to wear in October

Now things are getting colder. Even so you will still see people bathing either in the ocean or in the pool but mostly on sunny days.

Morning and evenings might require putting on a light layer of clothing. Oh and finally rain is drying up.

If you’re from the south, things might get a bit cold for your taste, and if you’re in the north, then it’s quite warm.

The best things to wear in October would be Johnny MBJ Wide Leg Palazzo Lounge Pants and for tops MIHOLL Women’s Long Sleeve Loose Blouse or ZC&GF Long Sleeve V-Neck Blouse.

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What to Wear in Naples Florida - Criss Crossing the USA (32)
What to Wear in Naples Florida - Criss Crossing the USA (33)

What to wear in November

Just the sound of November chill runs down my spine luckily in Naples it’s quite mild. You might not even need heavier clothing.

The truth is that the sun sets rather quickly so the cooler air demands layered clothing but nothing drastic since the temperature is between 60-80 degrees.

I recommend picking up something like a light sweater such as the Amazon Essentials Classic-Fit Lightweight Long-Sleeve V-Neck Sweater or Arach&Cloz Women’s V Neck Long-Sleeve Pullover Sweater.

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What to Wear in Naples Florida - Criss Crossing the USA (35)

Now if you fancy a sweater then this is your best choice: Floral Find Long Sleeve Lapel Half Zip Up Sweatshirt

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What to Wear in Naples Florida in Winter

This is what I love about winter in Naples it’s mild and super comfortable. With a few light layers you won’t have any issues. Best of all it’s the only part of the country where you can still enjoy the beach and the pool even in winter!

And ladies bring your favorite high heels because they can be worn all year around.

The locals call it low summer so yeah no serious winter clothing is needed.

Denim Jackets are hot this year Wrangler Authentics Stretch Denim Jacket is my go to choice

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Of course if it’s windy I prefer hoodies Hanes EcoSmart Full-Zip Hoodie Sweatshirt or Century Star Fuzzy Hoodies.

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What to Wear in Naples Florida - Criss Crossing the USA (39)

What to wear in December

If it’s December, it means the winter holidays. Well, you probably picked out your favorite clothes for the special night but what about during the day?

Most likely in the afternoon, you won’t need any layered clothing. Plus the chances of rain are minimal. So T-shirts and tank tops with sandals will be just fine.

Just to cover all bases I would choose Leggings or Jeans like No Nonsense Women’s Cotton Lounge Capri Legging or Levi’s 311 Shaping Skinny Jeans

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What to Wear in Naples Florida - Criss Crossing the USA (41)

And for the top long sleeve undershirt is highly appreciated.

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What to wear in January

Happy New Year! And what’s the best way to celebrate? Well it is a place where the weather is warm and no real rain so you can enjoy some amazing outdoor activities.

You can’t afford to miss a great sunset over the Gulf of Mexico.

Most people when hearing the word January they immediately think of freezing cold and snow. Well it’s different in Naples. It’s quite warm so you can enjoy wearing your sandals.

Just to cover all bases capris are a great choice my favorite one is LEE Relaxed-Fit Austyn Knit-Waist Cargo Capri Pants.

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Short sleeve shirts with a Jacket Amazon Essentials Classic-Fit Short-Sleeve Crewneck T-Shirt and Columbia Switchback Iii Jacket

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What to Wear in Naples Florida - Criss Crossing the USA (45)

What to wear in February

Since Naples is quite south it feels like early summer in February. That’s right you have read that correctly. It feels like summer is coming.

Best of all there’s little or no wind. When visiting Naples keep in mind that you’re there to have fun so enjoy the bright colors.

For the top, I would go with a sleeveless Jescakoo Short Sleeve Round Neck T Shirt.

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As for pants UNIONBAY Darcy Stretch 5″ Inseam Short or Levi Strauss Mid-Rise Bermuda Shorts

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What to Wear in Naples Florida - Criss Crossing the USA (48)

Conclusions on What to wear in Naples FL

We have reached the end of our trip, dear reader. As a matter of fact your trip is about to start so have a lot of fun in Naples.

As promised I’ve done my best to give you all types of clothing ideas for every season and every month of the year. Luckily Naples is warm all year round so you don’t have to pack any heavy clothes.

I hope you have already found a great-looking outfit to wear.

Also maybe you can help me out with something. Can you please share on social media what helped you the most from this article? It would mean a lot to me. Thank You.

Frequently Asked Questions:

What should I wear for dinner in Naples FL?

It really depends on your style you can go with the fabulous style like flowy maxi dresses or if it’s a bit warmer than short dresses. If you want something more laid back then lightweight pants and a blouse is the best thing. Grab your sunglasses as well because the sun sets late in Naples.

How do people dress in Naples Florida in December?

In December people wear a sweater if it’s a bit cooler other than that the typical swim gear with shorts hats and cover-ups.

How should I dress if I live in Florida?

The answer is the less fabric the better. Shorts and skirts are your best options because it doesn’t really get cold there.

What do Florida tourists wear?

For evening wear and for the sophisticated restaurant, you need to dress up to look the part and casual cosmopolitan is the right way to do it. As for the beach and daytime shorts and t-shirts with bathing suits that tourists wear in Florida.

What to Wear in Naples Florida - Criss Crossing the USA (2024)

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