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What to Wear in Key West: The Ultimate Checklist

If you’re prepping for your next Key West adventure, picking the right clothes is likely one of the top items on your to-do list. Clothes for Key West are laid-back yet chic, perfect for every one of your day’s adventures, and easy to transition from day to night. Playa Largo Ocean Residences has some helpful tips for what to wear in Key West, whether it’s your first time or a highly-anticipated return trip.

Starting Your Adventure from Playa Largo 

Playa Largo Ocean Residences, located in stunning Key Largo, is the perfect starting point for your journey to Key West. Just a two-hour drive away, Playa Largo provides an ideal base for exploring the beauty of the Florida Keys. This guide will help you plan your Key West wardrobe, ensuring you are stylish and comfortable for your trip.

Understanding the Key West Climate

Key West boasts a moderate, mild climate that is typically very warm during the day to slightly chilly at night. From November through February, lows can dip to the 50s at night, but even that tends to be rare, with average evening lows in the 60s. In the summer, average temperatures are in the upper 70s to upper 80s, while fall in Key West features mild temperatures of low to mid-70s to mid-80s. While rain in Key West is relatively rare, it occurs most often in September and October.

Day-to-Day Attire: Casual Meets Chic

Key West clothing style is casual, with most locals and visitors opting for laid-back shorts, sundresses, or loose, flowing pants. However, given the upscale vibe of Playa Largo Ocean Residences and Playa Largo Resort, you may want to elevate your style with a “Keys Chic” or “Resort Chic” approach. This style incorporates casual, breezy pieces with an elevated twist, such as a linen shirt paired with tailored shorts or a flowy maxi dress with statement accessories. Opt for light, breathable fabrics like linen or cotton and lighter shades that reflect the sunny, tropical environment.

Beach Attire

If you’re heading to the beach, think comfort and convenience. A dry-fit shirt or tank top is a great option that can serve as a cover-up over your swimsuit. Don’t forget sunscreen. Consider packing a beach towel, a wide-brimmed hat, sunglasses, and a lightweight cover-up, such as a breezy kimono or shawl—perfect for a stylish yet practical layer.

Dining Out in Key West

While eating out in Key West can be as upscale or as relaxed as you prefer, clothing is still fairly casual unless a restaurant’s dress code notes otherwise on their website or social page. To fit the “Keys Chic” vibe, consider dressy shorts or light slacks for men paired with a linen or cotton shirt. Women can opt for a flowy dress, a romper, or a skirt with a light blouse. These choices are comfortable yet stylish, perfect for a tropical evening.

Outdoor Activities: Tours and Excursions

Dress for comfort during your daily adventures in Key West. Every list of Key West outfit ideas should include a pair of comfortable walking shoes, flowy pants or shorts, and lightweight T-shirts. Whether you’re heading to a museum or walking around exploring local shops, this kind of outfit will keep you comfortable and cool.

Evening Wear

Key West evenings offer an opportunity to dress up while still maintaining comfort. For a more glamorous yet relaxed look, think “Resort Chic”: a maxi dress with elegant sandals for women or a tailored shirt with linen pants for men. While fine evening wear isn’t often required, packing one elevated outfit is a good idea for upscale dining or special occasions.

Special Considerations

While Key West is known for its sunny, warm days, unexpected weather events do occur. Prepare for pop-up rain showers by packing a few light layering pieces, such as a lightweight kimono-style garment or a shawl, and a rain jacket or poncho. For cooler evenings or more formal occasions, consider alternatives like a lightweight jacket. It’s also a good idea to have some clothing items designed for insect protection, like a lightweight long-sleeved shirt, since bugs are common in parks and other outdoor areas.

Embrace the Local Style While Enjoying Playa Largo Ocean Residences

Find your Key West clothing style when you visit us at Playa Largo Ocean Residences. Whether your adventures include fine dining, lazy beach days, shopping, or a combination of everything, you can ensure a fabulous, relaxing vacation by preparing your checklist ahead of time and packing for any eventuality. Contact us at Playa Largo Ocean Residences to learn more about our Florida Keys vacation rentals.

Image Credit: Maridav / Shutterstock

Plan Your Dream Wedding in the Florida Keys at Our Resort!

There’s nothing more stunning than a beachfront wedding, full of peaceful vibes and incredible views. If you’re on the hunt for wedding venues in Florida to make your special day truly magical, Playa Largo Ocean Residences are ideal. Our luxurious vacation property and our helpful team will help make your wedding the unforgettable occasion you dream of.

Ocean’s Edge Clubhouse

Fabulous celebrations start at the Ocean’s Edge Clubhouse. An exclusive recreational facility, the Ocean’s Edge Clubhouse tops lists of local seaside wedding venues. Discover panoramic views, concierge services, and much more, all designed to make your wedding and reception stress-free and enjoyable.

Unique venue features

The Ocean’s Edge Clubhouse offers unique features like a dedicated concierge service that can assist you and your guests with every need and a chic interior lounge where guests can socialize and unwind. You’ll also discover fine dining experiences at the clubhouse, curated and prepared by world-class chefs.

Exquisite oceanfront views and pristine beaches

One of the best features of the Ocean’s Edge Clubhouse is the incredible oceanfront views. When you host your wedding here, you’ll enjoy easy access to pristine Florida Keys beaches and panoramic views that invite your guests to drink in the beauty of the area.

Elegant indoor and outdoor spaces for ceremonies and receptions

Whether you want to host your wedding ceremony indoors or out, the Ocean’s Edge Clubhouse has the space to accommodate. Our versatile event spaces are designed to enhance the sense of community among guests, ensuring an easy flow of conversation and a good time for all.

Playa Largo Resort & Spa

The Playa Largo Resort & Spa offers even more opportunities to unwind and enjoy your special occasion. Unique among Florida Keys wedding venues, the Playa Largo Resort & Spa provides the ultimate luxury for you and your guests.

Ocean Spa

When you want to unwind after a busy weekend or get a relaxing massage before the evening’s festivities, the Ocean Spa at Playa Largo Resort & Spa is here for you. Rejuvenate and relax with a menu of services that includes body scrubs, massages, facials, and much more.

Club Playa

Club Playa provides a restful spot for guests who want to unwind in a hammock, enjoy ocean views, or chat with a friend. With the same dedicated service that we provide at every area of our resort, you’ll discover fresh towels on hand, refreshing beverages, and light snacks.

White Sand Beach

Florida beaches are known for their white sand and sparkling water, and at Playa Largo Ocean Residences, we offer easy access to 14 acres of stunning beachfront. Whether you love watersports or just want to bask in the sunshine, there’s something for everyone to enjoy at the beach.

Exciting Resort Events

Our oceanfront resort frequently hosts special events, including live music and shows, all for our guests to enjoy. Be sure to ask our event planners about any special performances or events happening in the area so you can plan your weekend accordingly!

Planning Your Dream Wedding

Wedding planning can be a lot of work. At Playa Largo Resort & Spa, we take the stress out of planning by providing all the help you need to make your big day a smashing success.

Dedicated wedding planner support

We offer dedicated wedding planner support, so no detail is left to chance. Working with a wedding planner makes the process a breeze, so you can live in the moment without worrying about scheduling and vendor arrangements.

Local attractions and activities

There’s always plenty to do in Key Largo. From sunup to sundown, the city has things to do. Whether you’re in town for a weeklong wedding extravaganza or a weekend ceremony, you can find attractions and activities to suit your fancy. Just ask your wedding planner what’s happening around your event time to get the scoop on local happenings.

Playa Largo Ocean Residences is the ideal wedding destination

Discover how easy it is to have your dream wedding when you plan your event at Playa Largo Ocean Residences. Our luxury oceanfront residences and resort is the perfect setting for a truly unforgettable ceremony. Contact us today to learn more about our luxury Key Largo resort!

Image Credit: NeonShot / Shutterstock

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