A Floridian Winter Outfit Guide 15 Outfits With Links For Your Next Trip To Florida
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 clothing items and/or photo locations)
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!
photo location ✈ Casey Key Resort Beachfront
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.
photo location ✈ Casey Key Resort Beachfront
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!
photo location ✈ Casey Key Resort Beachfront
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 location ✈ 205 Casey Key Road
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.
photo location ✈ Casey Key Resort Beachfront
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.
photo location ✈ Nokomis Beach
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 of a heel but they still match my bag perfectly. This adorable criss-cross top is Princess Polly.
top // shorts // shoes // purse
photo location ✈ 217 Casey Key Road
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.
photo location ✈ Nokomis Beach
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!
photo location ✈ 212 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.
photo location ✈ Casey Key Resort Beachfront
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.
photo location ✈ 306 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.
photo location ✈ Casey Key Resort Beachfront
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.
photo location ✈ Casey 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!
photo location ✈ Leachs Key, FL
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!
photo location ✈ 312 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
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