So, you’re headed to Key West? Lucky you! This beautiful little island is full of sunshine, saltwater, and laid-back vibes. But if you’ve never been before, you might be wondering: what to wear to Key West?
It’s not quite as simple as packing a swimsuit and flip-flops—Key West outfits have a unique style that reflects the easygoing, tropical, and sometimes quirky vibe of the island. Whether you’re chilling on the beach, exploring Old Town, or heading out for a night on the town, there’s a perfect outfit for every part of your trip, amongst all there is to do! I can’t wait to show you some of my favorite Key West outfit ideas for every occasion you’ll find yourself in!
What to Wear in Florida
Packing for Key West: Start With the Basics
Before we get into specific outfit ideas for Key West, let’s talk about what to pack for Key West in general. The weather in Key West is hot and humid, so light, breathable clothes are a must. The island doesn’t require anything too formal, but you’ll want to make sure you’ve got the basics covered—especially since you’ll be spending a lot of time outdoors.
Essential Items for Your Key West Packing List:
- Sunscreen: The sun is intense, and you’re likely to be outdoors for most of your trip. Pack something with high SPF (reef-safe sunscreen, please!).
- Sunglasses: A stylish, oversized pair is both functional and chic.
- Swimwear: At least two swimsuits to rotate between. You’ll find yourself at the beach or in the pool most days.
- A hat: A wide-brimmed hat not only keeps the sun off your face but adds a bit of glamour to your look.
Comfortable Footwear for All-Day Exploring
Whether you’re walking along the beach, or exploring downtown areas, comfortable shoes are essential. Florida’s hot climate calls for breathable and easy-to-wear footwear that won’t slow you down.
- Flip-Flops or Sandals: These are perfect for beach days or casual outings. Opt for waterproof sandals that are easy to rinse off after a day in the sand.
- Walking Sneakers: If you’re spending the day walking around exploring the towns, hiking trails, the outdoors, or even just shopping districts, you’ll need supportive sneakers for all-day comfort.
- Wedge Sandals: For evenings out, a pair of wedge sandals are comfortable and stylish.
Pro Tip: Bring a couple of pairs of shoes that can handle different activities—flip-flops for the beach, sneakers for theme parks, and wedge sandals for dinners and nights out.
Lightweight Fabrics Are a Must
Florida’s weather can range from warm to hot year-round, with plenty of humidity, especially in the summer months. Opt for breathable, lightweight fabrics that keep you cool and comfortable no matter the season.
- Cotton Sundresses: Perfect for daytime wear, choose flowy, breezy dresses in tropical prints or bright colors. Sundresses can easily transition from a beach day to a casual dinner.
- Linen Shorts and Tops: Linen is your best friend in Florida’s heat. Choose loose-fitting linen shorts and a matching crop top or a relaxed button-up shirt for a casual yet polished look.
- Jumpsuits and Rompers: One-piece outfits like jumpsuits or rompers are ideal for effortless style. Look for options in lightweight materials that are easy to slip on for day-to-night transitions.
Pro Tip: Stick to light shades like white, beige, and pastel colors to reflect the sun’s rays and stay cool throughout the day. Tropical prints and patterns are a perfect match for Florida’s lively atmosphere.
Swimwear Essentials
No trip to Florida is complete without packing stylish swimwear! Whether you’re lounging by the pool, visiting the beach, or hitting a water park, swimwear is a big part of your wardrobe for a Florida vacation.
- Bikinis: Fun, mix-and-match bikinis are ideal for beach days. Opt for bold colors, florals, or even metallics for that extra glam.
- One-piece Swimsuits: Choose a sleek one-piece for water sports or days you want more coverage. Look for styles with cut-outs or plunging necklines to keep things fashion-forward.
- Cover-ups: A sheer sarong, kimono-style cover-up, or beach dressis essential for throwing on when you leave the water. These pieces are stylish enough for poolside dining or walking along the boardwalk.
Pro Tip: Don’t forget to pack a wide-brimmed hat and oversized sunglasses for extra sun protection while lounging in style.
Weather-Ready Packing Tips
Florida’s weather can change quickly, especially during the rainy season. Be prepared for sudden rain showers and fluctuating temperatures with smart packing.
- Rain Jacket or Poncho: Florida’s thunderstorms can come out of nowhere, so pack a light rain jacket or poncho to stay dry without overheating.
- Compact Umbrella: A small, foldable umbrella is great to throw in your bag for unexpected rain.
- Light Layers: For cooler evenings or air-conditioned indoor spaces, pack light cardigans or scarves that can easily be added to your outfit
Versatile Bags for Different Occasions
Your bag can make or break your travel experience. In Florida, you’ll want options that suit both your beach days and city excursions.
- Beach Tote: A large, stylish tote bag is perfect for carrying towels, sunscreen, and snacks to the beach. Look for one that’s waterproof and sand-proof.
- Crossbody Bag: For walking around theme parks or downtown areas, a crossbody bag keeps your essentials close and secure, leaving your hands free.
- Clutch or Mini Bag: For evenings out, a mini bag or clutch is ideal for carrying just the essentials while looking polished and stylish.
Key West Outfit Ideas
Swimsuit + Sarong
Let’s face it: you’re probably going to spend a good chunk of your trip near the water, so having a Key West beach outfitready is a must. You want to be comfortable, stylish, and protected from the sun. Pick a fun tropical swim suit that fits you well– weather a two piece or a one-piece. And then throw on a colorful sarong or lightweight beach cover-up. Pair it with comfortable and cute sandals, and this is perfect for the beach itself or a bar cocktail.
Why it Works: Comfy and stylish, you’ll channel the warm weather and looks when at the beach! Cover ups help protect you, and you’ll get to really enjoy all Key West has to offer.
Breezy Sundress + Sandals + Jean Jacket
Sundresses are essential to Key West attire: light, flowy and effortless. They’re comfortable for walking around the island, grabbing linch, or even popping into a world-famous art gallery. Bonus points for dresses with tropical prints or bold colors. Complete the look with sandals– and if you need to dress it up, pull out those scrappy sandals rather than flip-flips! Jean jackets are also great if you go inside somewhere and need protection against the AC.
Why It Works: We love looks that are versatile no matter where we are going: so dresses that can take us to lunch or to museums are great! Dress it up or dress it down and you are good to go.
High Waisted Shorts + Tank Top
When the weather is warm and you still need comfort, shorts and tanks are great for daytime activities. Those high waisted denim or linen shorts paired with a flowy tank is comfortable yet stylish. Or if you like some sun protection, graphic t-shirts work as well, and can be more relaxed. Pair with sunglasses and you’re good to go!
Why It Works: Relaxing outfits don’t have to sacrifice style: protect your skin, get comfortable, and feel good walking around and exploring shops, bars, or even walking the beach if you don’t want to get in the water.
Romper + Sneakers + Sweater
A cute romper is comfortable and stylish. It is perfect for walking around and exploring! And you can chose if you want shorts or long pants. Plus you then get to chose whether you want a fun pattern or a solid color. These are the best outfits for Key West since they combine fun with practicality. Pair with sneakers or flats if you’re walking a lot!
Why It Works: Rompers are prefect for comfort and style as they dress things up and leave you with endless options. You can wear this literally anywhere!
Linen Pants + Tank or Button-Up Shirt
Linen is your friend in Key West. It’s light, breathable, and perfect for the tropical climate. A pair of linen pants combined with a simple tank top or a button-up shirt gives you an effortlessly stylish look. You can tuck it in or knot it at the waist for a more relaxed vibe. These kinds of outfits are ideal for an afternoon stroll or a visit to one of Key West’s laid-back restaurants.
Why This Works: Light weight fabric is needed in Florida, in all seasons. Linen pants are easy on the beach, but also comfortable to dress up or dress down. Strolls and restaurants will love to see you coming.
Key West Graphic Tee + Jeans or Skirt
If you’re feeling casual but still want to represent Key West, throw on a graphic tee featuring some iconic imagery of the island—think palm trees, sunsets, or vintage Key West postcards. Pair with your favourite jeans or a cute skirt for a more elevated look. You’ll fit right in with the locals!
Why It Works: Repping Key West is fun, and graphic tees are comfortable! You can add personality and formalness with a skirt, or tune it down with favorite jeans. Fitting in is key!
Maxi Dress + Heeled Sandals + Statement Jewelry
A flowy maxi dress in a tropical print is perfect for evening vibes. Whether you’re hitting up a rooftop bar or enjoying dinner at a fancy seafood joint, this outfit feels relaxed but still dressy enough for a night out. Pair with heeled sandals or wedges to elevate the look without overdoing it.
Why It Works: Evening vibes let you dress up and enjoy more of the night life of Key West, so your outfit should reflect this! Relaxed yet dressy is perfect for elevation.
Sleek Jumpsuit with Cutouts + Strappy Sandals + Clutch
If you’re looking for something a little more fashion-forward, try a chic jumpsuit. You can go for a bold colour like coral or emerald green, or a simple black one if you want to keep things sleek. Add strappy sandals and a statement clutch to make it feel more night-appropriate.
Why It Works: Sometimes you just gotta do some form of pants: fashion forward jumpsuits allow you to elevate your style when exploring the nightlife and evenings.
High Waisted Skirt + Crop Tops + Sun Hat
For something fun and flirty, a high-waisted skirt paired with a crop top is a great choice. Look for a skirt with a flowy, feminine vibe—something you can twirl in while grabbing a drink at a bar. Crop tops in light fabrics or with eye-catching details will elevate this outfit.
Why it Works: This brings our personality! The island comes alive at night, so cute Key West nightlife outfits will have heads turning and ensure you are still comfortable and breezy.
Essential Extras To Pack For Florida
Here are a few things that you may want to pack for Florida! Some of these you may already have, or you may want to get in advance of your trip. I LOVE my waterproof phone case, it is great and I use it for all of my Florida trips, especially the springs and the beach!
- Sunscreen (reef-safe for beach days)
- Bug spray (especially for outdoor adventures)
- Reusable water bottle to stay hydrated in the heat
- Sunglasses with UV protection
- Wide-brimmed hat for sun protection
- Light scarf for breezy evenings or sun protection
- Portable phone charger for long days out
- Compact umbrella or rain poncho for sudden rain showers
- Waterproof phone pouch for beach and poolside
- Flip-flops or water shoes for beach days and water activities
Wrapping Up: What to Pack and Wear for Key West
No matter what part of Key West you’re visiting—beach, bars, or historical sites—there’s an outfit for it all. The key to Key West outfit ideas is keeping it light, breezy, and fun, with just the right amount of chic to suit the island’s relaxed yet fashionable vibe.
So, when you’re figuring out what to pack for Key West, keep your wardrobe versatile. Think light layers, breathable fabrics, and comfortable shoes. Most importantly, don’t forget to let your personal style shine through while embracing the laid-back island vibe. Whether you’re lounging on the beach in a cute cover-up or hitting up Duval Street for some nightlife fun, there’s no wrong way to dress in Key West—just make sure you’re comfortable and ready to enjoy everything this stunning little island has to offer. Enjoy your trip, and don’t forget the sunscreen!
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