A Floridian Winter Outfit Guide 15 Outfits With Links For Your Next Trip To Florida (2024)

Just before Christmas, I took a trip to Nokomis, Florida to spend a few days relaxing by the water, shooting photos, and capturing content for the Casey Key Resort! I had the best time and being in the Florida sunshine in the dead of winter was truly the serotonin boost I needed before a brutally cold winter began.

Now that the holiday season has died down, I’m finally getting around to sharing my outfit guide with you. This trip was the perfect opportunity to pull out all of the clothes I received towards the end of summer but never had the chance to wear!

With so many of you planning a winter trip to Florida to escape reality, I figured this post would be helpful to many of you! As per usual I’m breaking down everything I wore throughout my trip while linking each individual item (or something similar) and directions to each photo location! Enjoy.

(click pink text for links to clothingitems and/or photo locations)

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LET’S TRAVEL

If you know you know, I love to travel in a matching sweat set. This lightweight knit is from SheIn and was perfect for the transition from chilly Maryland to sunny Florida. I wore the top buttoned up as a sweater but left a cami underneath so I could leave it open as a cardigan once we arrived at our final destination. These pants fit similar to yoga pants with the cutest flare along the bottom.

I would have preferred flip-flops with this outfit but sneakers it was as we had a long day of travel ahead of us. Of course, my big ole floppy hat and straw hat wouldn’t fit so I carried them on, and honestly, they were the perfect addition o this outfit.

I got this luggage set in September and have used it for every trip since. I’m obsessed with the matching pieces and could fit so many outfits in this for my long trip!

sweater // pants // sneakers

photo locationCasey Key Resort Beachfront

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TIE-DYE MAXI

We arrived at our final destination later in the day so we got dressed and went straight to dinner to enjoy our first meal by the water. I slipped into a cute tie-dye maxi for the first night. I got this back in July from Fashion Nova and never had the chance to wear it. I figured Florida was the perfect excuse to pull it out.

dress

photo locationCasey Key Resort Beachfront

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GLOWING IN GREEN

Woke up in paradise and spent the morning frolicking around our resort, exploring + grabbing some photos. I wore several swimsuits throughout this trip but this Cupshe one was one of my favs. This top is super flattering and yet gives you all kinds of support. The bottoms were cheeky but still had lots of coverage around the front!

bikini

photo locationCasey Key Resort Beachfront

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CROCHET CUTIE

Walking around town doing a little exploring in this fun crochet tank. I scored this from Romwe and am obsessed— that tie-front detail makes your boobs look fantastic! These linen pants have come on several trips with me now and they are some of my favorites. Few pieces I keep in rotation as frequently as these—they are from Petal and Pup and are double-lined + so comfortable. They work for both a day of travel or hanging by the beach. They are that perfect ankle length that looks so good with a chunky heeled shoe. I wore these pink ones quite a few times throughout our trip.

top // pants // shoes // purse

photo location205 Casey Key Road

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HELD UP IN THE HAMMOCK

This kini is another fav! I’ve had this one for years and love it so much that I have it in several different colors. You know me—the yellow was definitely my favorite. If you’re looking for a suit that’s family friendly with lots of coverage all around, this is the one! It’s got a cool, towel-like texture to it.

bikini

photo locationCasey Key Resort Beachfront

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DOWN BY THE WATER

Soaking up the Florida sunshine in the cutest one-piece from Cupshe! I’m not usually a fan of suits with a low back + high cut but this one was perfect. Plus, with a belted waist this one was incredibly flattering. I bring this floppy hat on every beach vacay—it’s an old favorite from TJ Maxx but I’ll try my best to link something similar.

swimsuit // hat

photo locationNokomis Beach

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BEACH DAY STROLL

I think so often people feel they have to dress differently because it’s December in Florida. Perhaps in the more residential areas people dress more for the calendar year, but in these resort-like beach towns, everyone was dressed for the weather. And in my eyes, sunny and seventy-five means shorts and sandals!

I grabbed these shorts from Windsor early last summer and wore the absolute heck of them. Sadly they are sold out but I’ve done my best to link a similar pair. These shoes are one of two pairs of espadrilles I brought. I love my thin Dolce Vita ones but if you’re looking for a cheaper alternative, these are great too! They have a little bit shorter ofa heel but they still match my bag perfectly. This adorable criss-cross top is Princess Polly.

top // shorts // shoes // purse

photo location217 Casey Key Road

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LAZY DAY

Spending the day enjoying this incredible view in the cutest smocked bathing suit. I love this one as it stays in place while swimming + gives the perfect tan line.

bikini

photo locationNokomis Beach

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70s CHIC

Feeling like a seventies babe posing in front of the cutest little VW van in this number. I grabbed this one-piece swimsuit over the summer and had been saving it for a fun trip. For lunch by the water, I slipped a pair of white linen shorts over top. These are from Princess Polly and although they are mini they are too cute! I wore them so much throughout this trip. These pink chunky platforms matched the suit perfectly and gave me a little extra lift— LOVE!

swimsuit // shorts // shoes

photo location212 Casey Key Road

HIGH RISE HOTTIE

One of my favorite suits from the trip was this blue high-waisted kini. This is another Cupshe find and the quality was fantastic. It has the most flattering bottoms ever—hitting you at the smallest point of your waist with a high cut along the sides to elongate the legs. Plus, it has just the right amount of cheekiness. This top has sweet tie-side details and a small clasp along the back. I felt so confident in this as I met a friend’s parents + spent the day on their boat.

bikini

photo locationCasey Key Resort Beachfront

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LITTLE BLACK SET

This two-piece set was another SheIn find from the summer that I’d been saving. It’s this stretchy cotton material that was incredibly soft. With a solid tube top and a fun asymmetrical skirt, these two pieces could easily be mixed and matched to maximize your suitcase! I love the two together for dinner out or grabbing drinks with friends.

set // shoes // purse

photo location306 Casey Key Road

MORNING EATS

Chilling around the resort enjoying an açaí bowl to start the day. These wrap front tops are so popular right now and they can be worn several different ways. I personally love them wrapped around the neck and then around the torso. Just a simple pair of white cut-offs make the perfect combo together.

top // shorts // purse

photo locationCasey Key Resort Beachfront

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SHOWER STOP

Our property had the cutest little outdoor shower area to rinse off before heading back to your room. Of course, I had to take advantage of this photo op! I have this suit in several different colors and it’s one of my favorites. The ring detail along the center is so flattering + you can never go wrong with a simple triangle suit. Although if you have larger boobs I would definitely recommend skipping out on this one.

bikini

photo locationCasey Key Resort Beachfront

SUNSET ON THE BEACH

Off to catch the sunset on the beach and snap a few photos. It feels obligatory to do it in a white dress, I mean come on! This one had the cutest babydoll fit that was perfect for twirling. With loose, self-tying straps this was so flowy which was definitely ideal after a day of sun. I’m wearing my go-to straw shoe + purse combo!

dress // shoes // purse

photo locationLeachs Key, FL

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WALK DOWN VENICE

Enjoying one last morning in Florida with breakfast and window shopping along the mains trip in Venice Beach. There were tons of older people here so a sundress was a good choice. I felt this pink midi dress was definitely appropriate. You can truly never go wrong with a dress—they are the easiest pieces to style and they fold up so easily taking up hardly any room in your suitcase. Hence, how I was able to fit so much into my suitcase!

dress // shoes // purse

photo location312 Miami Ave Venice

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Phew, talk about packing in a ton of outfits into just a few days! Fingers crossed a winter trip to Florida can become something annual—I had the best time soaking up the sun. Stay tuned for my travel guide going live Friday. That’ll be chock full of restaurant recommendations, resort reviews, and things to do throughout your stay. Talk soon!

With love, McKenz

Latest Post:Setting My 2022 GoalsRelated Post:Miami Swim Week Recap 2021Instagram:styledbymckenz//YouTube:McKenzie Morgan//Pinterest:mckenzmorgan

A Floridian Winter Outfit Guide 15 Outfits With Links For Your Next Trip To Florida (2024)

FAQs

What do people wear in Florida in winter? ›

Florida isn't known for freezing winter temperatures. A long sleeve shirt can substitute a jacket during a breezy day. At times, the sun makes it too hot for a full jacket. A simple long sleeve shirt has enough material to protect yourself from potential wind chill while still being light enough to handle the heat.

What to wear in Florida at 70? ›

70 degrees is still sweater weather, depending on your location, so you can't go wrong with a knitted bandeau and cardigan set. If you're not afraid to show a little skin, pair the knitted pieces with baggy low-rise jeans. Not really your style? We also recommend high-waisted jeans or a midi skirt for more coverage.

How do people dress in Orlando in December? ›

Pack Layers

That can be cold, especially in the shade and after dark. The highs in December in Orlando on average is 75 degrees. The best way to make sure you are comfortable is to dress in layers. Make sure you have long sleeve shirts, jackets, hats, and bring gloves for the little ones.

Do Floridians wear white in winter? ›

Because winter, summer, spring, or fall, white jeans are always a fashion “YES” in Florida!

Is it OK to wear white in Florida? ›

In Florida the clothing cops are more lenient. They may frown on white accessories teamed with dark business or evening wear. But they give the nod to white when it is confined to casual, resort-type settings – and provided the weather is reasonably warm. The real problem with white is the way it shows dirt.

Do you ever wear sweaters in Florida? ›

Do people wear sweaters in Florida? In the winter people in Florida often wear sweaters or jackets. Some people in Florida are so used to the hot weather, than when it gets cold, or even cool, they dress up very warmly.

What should a 65 year old wear? ›

For durability, versatility and pure comfort, it's hard to beat the breezy sophistication of breathable fabrics like cotton, linen and chambray. Lightweight blends are a perfect base for a minimalist wardrobe for a 65-year-old woman. Beyond comfort, these textiles have a beautiful drape and flow on the body.

What should a 70 year old woman wear? ›

When choosing clothes for elderly ladies, look for versatility in your garments, for example: Loose-fit skirts with elegant prints and pleats that spread easily while sitting. Trousers that pull on easily with back waist elastication for added comfort. Cardigans without buttons that are warm and easy to put on.

What age is considered elderly in Florida? ›

The age at which one is considered a senior citizen in Florida is generally between 60-65 years of age, it however varies depending on the context. For example, the Florida Department of Elder Affairs defines a senior citizen as someone who is 60 years of age or older.

What to wear on a plane to Florida? ›

Find the right balance between style and comfort

No one wants to sit through a seven-hour flight in constricting jeans or too-tight shoes — soft, stretchy, and stylish clothing is the way to go. Athleisure sets, loose-fitting pants and tops, and slip-on shoes all make for comfy and convenient plane outfits.

What do you wear to Disney when its cold? ›

Pack a coat for Disney World in the wintertime.

This isn't needed for every winter trip to Disney, so be smart and check the weather before your trip. If it is predicted to be 50 degrees or below and windy, you will want to pack a coat. I prefer bringing one with a hood to keep my ears warm as needed.

Do you need a jacket in Orlando in December? ›

Packing for Orlando in December

Think about dressing in layers so you are ready for any spike or drop in temperature. December is a good time to bring both long and short-sleeve shirts, a pair of shorts, and jeans or long pants, as well as a sweater or sweatshirt.

What does winter look like in Florida? ›

In the northern regions of Florida, winters are known for their cooler temperatures and abundant rainfall. Moving towards the central regions, rainfall decreases slightly, and autumn-like temperatures appear for a few weeks each year—even during the daytime.

Can I wear linen in winter in Florida? ›

With average highs in the mid 70's even in winter, and high humidity throughout the year, Miami is a destination you will want to bring your Airthreads linen shirts to. And it's not just Miami. Key West, Orlando, Daytona are all hot and humid Florida destinations to keep cool in your linen apparel.

Why can't you wear white in the winter? ›

Some historians say brighter clothing was worn by affluent groups who could afford to leave town for a warmer coast when the leaves began to change. Subsequently, it became socially accepted that those who didn't have the money to take fall and winter vacations shouldn't don white after the last summer holiday.

Do people wear shorts in Florida in January? ›

Comfortable clothes that you can layer: Florida's wacky weather sometimes lets us wear T-shirts and shorts during January, but for the most part, it's better to bring clothes that you can layer, such as a flannel shirt or spirit jersey. Comfortable shoes: Opt for sneakers or boots that are worn in.

What type of clothes do Floridians wear? ›

Floridians live in shorts. Unless, of course, there's a cold snap. For women, denim shorts—ripped, rolled, distressed—go with everything. For men, consider light-colored chino shorts to keep you cool in the heat.

What do people in Miami wear in the winter? ›

Miami stays warm and humid all year round, even in the winter months, so you definitely won't need a winter jacket. You can also leave other winter items at home, like sweaters, flannels, and boots. While Miami can be casual and beachy during the day, at night it's a lot more dressy.

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