10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (2024)

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (1)

I was in dire need of some sunshine so I packed my bags and flew to Florida for the week. I split my time between Key West (new to me) and Saint Petersburg (my old stomping grounds) and it was a blast. There’s nothing I love more than being by the water, especially during fall.

Not sure what to pack for a fall trip to Florida? Neither was I so I brought a little bit of everything. Despite temperatures dipping everywhere else, Florida greeted me with endless sunny days and eighty-degree temperatures. If I hadn’t looked at the calendar I would’ve thought it was the middle of June, haha. Today I’m rounding up all ten outfits + bikinis I wore throughout my stay complete with links to shop.

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (2)


dress || sandals || purse

photo location✈ Marriott Key West Beachside

You know those cute boutiques you keep getting Instagram ads for? Well, this is your sign to fall for them and just place the order. I had been seeing Fortunate One all over my Instagram feed and finally placed an order for five of their dresses and was just blown away by the quality and fit of them all! This pale yellow maxi was definitely my favorite piece of the order.

Everything from the plunging neckline to the puff sleeves to the lace-up back weresoflattering. With a pair of raffia sandals and a cute little clutch to match, this was the perfect look for dinner by the water. If you’re shopping for vacation clothes, I highly suggest checking out this site. I was super impressed!

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (5)


top || bottoms

photo location✈ Marriott Key West Beachside

I knew it would be warm but I wasn’t *entirely* sure it would be warm enough to lay out on the beach. To my surprise, the UV was 10 every single day with temperatures in the eighties. The water was as warm as a hot tub too! Needless to say, I spenta lotof time in a bikini.

I’m making Florida feel like “fall” with a chocolate brown bikini. This is a new style from one of my favorite sustainable swimwear brands, Svn Swim. The quality of these suits is unreal with a buttery soft fabric, and tiny silhouettes that hug every curve. This collection is launching to the public in just a few weeks. Stay tuned!

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dress || sandals || purse

photo location✈ Pass A Grille Beach Sign

I discovered the brand Araminta James earlier this year and have been hooked on the sustainable, small business ever since. They have timeless pieces in the cutest colorways, perfect for your next warm-weather vacation. I have this dress in the short version and was thrilled to see they released it in a midi style for the fall. This cornflower blue is the prettiest hue for a beach trip!

This has a smocked bodice, adjustable straps, and deep pockets which is my favorite touch. Although this piece is a bit of an investment, it was made to last for years to come. I paired it with my favorite raffia “heels” and lemon purse. This is the perfecct outfit if you’re taking updated family portraits on the beach.

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (11)


top || bottoms

photo location✈ The Don Cesar Beach Access

Who doesn’t love a little black bikini?! I bring one with me oneverytrip for a little confidence boost. This is another sustainable style from a small business called Kamari Swim. The fabric they use feels like butter with a seamless fit that’sso flattering. I am typically a true XS in bikini tops however, this one definitely runs tiny. I suggest going up if you’re thinking about purchasing. I’m wearing my true XS in the bottoms and they fit me like a glove, with a cut that made my tush look extra perky. Love!

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (14)


dress || purse|| sandals

photo location✈ Tiki Docks Saint Pete

Who doesn’t love slipping into a sundress after a long beach day?! My idea of making my wardrobe fall-ready is by wearing maxi dresses rather than minis, haha. As you can tell, I packed several for this trip but this one from by ALALA was one of my favorites. I scored this from a small business in Charleston, South Carolina in the spring and finally had a reason to wear it!

This style is an easy breezy cotton that’s perfect for a September trip to Florida. With a pair of sandals and a clutch, it was perfect for sunset drinks by the water.

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set || bikini || flip flops || bag

photo location✈ Downtown Key West

One thing you definitely can’t go to Florida without is a linen set. I wore this lightweight button-up and shorts duo from Araminta James almost every single day. I threw it over a bikini for a coffee run and boat day then wore it buttoned the next for a casual dinner. It even worked as a comfy travel day outfit. They have this set in a gazillion colors and Ineed to grab it in another color. I seriously can’t remember the last time I wore something this much.

Our cute matching lemon suits are from SheIn! Under $10 with my code Q4mckenz15.

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (20)


dress || sandals || purse

photo location✈ Marriott Key West Beachside

This gorgeous green dress was another Fortunate One find. It has two long straps that can be tied several different ways—my personal favorite is straight back for a plunging neckline with a ciss cross along the back. Super sexy for dinner and drinks but of course, you can play around with it and find which way you feel most confident in. Love a versatile piece— you can use code MCKENZIE0 for 10% off.

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (23)


dress || sandals || clutch (handmade in Cabo)

photo location✈ Marriott Key West Beachside

I’m a firm believer that youhaveto pack a white dress for every beach vacation. Whether you’re taking family photos or just want a cute Instagram selfie, there’s no better piece to compliment your fresh new tan. This beautiful dress is from Revolve’s Tularosa line. It’s definitely a splurge but one of those pieces you can wear for so many different occasions. I also have the SheIn dupe that I will leave linked in case you’re looking for a budget-friendly option.

Dress this up or down. My clutch was handmade in Cabo so unfortunately I cannot link it but isn’t it adorable?! One of my favorite finds.

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photo location✈ The Don Cesar Beach Access

Unfortunately, sustainable suits equal a higher price point. I’ve been trying hard to wear and share a mix since I know everyone has different needs. If you’re wanting a good under $10 bikini, this is one of my favorites. It comes in several different colors but this purple was just calling my name. You just can’t go wrong with a little string bikini—super flattering and gives you a good, basic tanline.



photo location✈ The Don Cesar Beach Access

If you’re planning on spending most of your day in the water, I highly suggest this bikini. It’s one of those tops that haveno self-ties, clasps, etc. so there’s zero chance of this getting knocked off by a wave. The bottoms are also solid with a cheeky cut that makes your tush look extra perky. I have this suit in seven colors now… it’s one of the best in my opinion!

Don’t forget you can stack my code Q4mckenz15 to get 15% off your entire purchase.


10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (31)

If you’re headed to the Florida Keys, chances are you’re going to be spending every evening bar hopping. While there are some cities I would wear my favorite dress out in, this was certainly not one of them. The bars are true dives with sticky floors and bras hanging from the ceilings, lol. You’ll want to pack a few tiny tops, denim shorts, and sandals to wear for your nights out. Unfortunately, I don’t have pictures of the outfits I wore out each night (we were busy taking shots, haha) but I’m linking everything I brought and styled for you to shop. It’s super casual!


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No Florida trip is complete without a longmorning walk along the beach.I packed several workout sets from Free People, Lululemon, and Aerie. Again, I didn’t take pictures of these, but I’m leaving them linked for you to shop. I ended up bringing my Adidas sneakers on this trip rather than my Hokas and immediately regretted it. I’m not sure I can go for my Adidas after months of wearing truly supportive sneakers.

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Chances are you’re reading this post because you’re headed on a warm-weather trip sometime soon… in which case I hope you have an amazing time. Nothing will recharge your batteries like a little Florida sunshine and saltwater. I had an amazing time in the Keys and Saint Pete and hope to be back soon. In the meantime, I’m prepping for my big trip to Europe… just ten days till my month-long adventure begins. Stay tuned.

With love, McKenz

Latest Post:9 Basic Fall Outfit Ideas To Recreate || 2023Related Post:10 Outfits To Wear In Cabo, Mexico This SummerInstagram|YouTube|TikTok| Pinterest


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As an expert in travel and fashion, I've had the opportunity to explore various destinations and curate a wardrobe suitable for different climates and occasions. I have a deep understanding of the fashion industry, including knowledge of sustainable fashion brands, seasonal trends, and the significance of versatile and stylish vacation attire. I have firsthand experience with packing for warm-weather trips and understanding the importance of choosing the right outfits for different activities and locations.

Concepts Used in the Article:

The article covers various concepts related to travel, fashion, and lifestyle. Here's a breakdown of the concepts used in the article:

  1. Travel Destinations: The article discusses two travel destinations in Florida, Key West and Saint Petersburg, and highlights the experiences and activities in each location.

  2. Fashion and Outfits: The article provides detailed descriptions of ten outfits, including dresses, bikinis, and other clothing items suitable for a warm-weather vacation in Florida. It emphasizes the importance of selecting versatile and stylish vacation attire suitable for different occasions such as beach days, dinner by the water, and casual outings.

  3. Sustainable Fashion: The article mentions sustainable swimwear brands and sustainable fashion pieces, highlighting the importance of environmentally friendly clothing options for vacation wardrobes.

  4. Small Businesses and Boutique Shopping: The article promotes boutique shopping and highlights specific small businesses and brands, advocating for unique and high-quality fashion pieces.

  5. Accessories and Footwear: The article emphasizes the significance of pairing outfits with appropriate accessories and footwear, such as sandals, purses, and handmade clutches.

  6. Budget-Friendly Options: The article provides recommendations for budget-friendly fashion items, including bikinis and alternative options for splurge-worthy pieces.

  7. Beach and Water Activities: The article discusses beach activities, including lounging on the beach, swimming, and enjoying drinks by the water, and suggests suitable outfits for these occasions.

  8. Evening and Night Outfits: The article mentions the need for casual evening outfits for activities like bar hopping, along with recommendations for tiny tops, denim shorts, and sandals.

  9. Workout Wear: The article briefly discusses the importance of packing workout wear for activities such as morning walks along the beach, and recommends specific brands for workout sets and supportive sneakers.

  10. Travel Plans and Future Trips: The article concludes with a mention of future travel plans and a teaser for an upcoming trip to Europe, adding a personal touch and a glimpse into the author's travel experiences.

These concepts collectively provide a comprehensive guide to packing and styling for a warm-weather vacation in Florida, while also promoting sustainable and versatile fashion choices for travelers.

10 Outfits To Wear On Your Florida Vacation This Fall Florida Outfit Guide Fall 2023 (2024)
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