Poolside to Beaches: How to Style Swimwear and Cover-Ups in Orlando

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Living in Orlando means sun, fun, and a whole lot of poolside time. Whether you’re lounging at a resort, enjoying a day by the pool, or heading to a beach bar after a swim, knowing how to style your swimwear and cover-ups can make a huge difference. As someone who’s spent over a decade helping women find the perfect outfits for every occasion, I’ve learned how to strike that delicate balance between comfort and style. When it comes to swimwear and cover-ups, it’s all about feeling confident and effortlessly chic—whether you’re catching some rays or heading to an evening party.

Katy wearing a swimsuit at Cocoa Beach.

The Power of a Good Cover-Up

A great cover-up is a game changer. Not only does it provide some extra sun protection, but it can also elevate your entire look. What you choose to pair with your swimsuit can take you from the pool to an impromptu lunch or drinks by the water without missing a beat.

My go-to cover-up recommendations:

  • Maxi dresses: A flowy maxi dress in a lightweight fabric like cotton or linen will give you full coverage without making you feel overheated. Pair it with a wide-brimmed hat and a sleek pair of sunglasses, and you’re poolside chic.
  • Kimono-style wraps: These are an easy way to stay cool while adding a little drama to your look. The airy fabric and loose fit give off a boho vibe that works perfectly for Orlando’s laid-back resort scene.
  • Kaftans and tunics: If you’re looking for something that’s both stylish and versatile, a kaftan can take you from poolside to party time with ease. Look for one with interesting prints or metallic accents to make it feel special.
  • Shorts and flowy tops: When it’s too warm for a full-on cover-up, opt for a cute pair of high-waisted shorts paired with a sheer, lightweight blouse. It’s a simple look that’s both comfortable and stylish.

Styling Swimwear for Day and Night

One thing I’ve learned over the years is that the right swimsuit is only half the battle. The way you style it makes all the difference. Whether you’re staying poolside or heading to a dinner date, there are simple ways to make swimwear work for different moments of the day.

  • Daytime looks: Keep it easy and breezy for a daytime swim. A well-fitted one-piece with a classic design (think stripes or solids) can be paired with a fun, patterned kimono or sarong. Throw on some slides or flip-flops and you’re good to go.
  • Evening transitions: Heading out for a casual dinner or beach party? A cover-up with a touch of sparkle or an elegant draped design works beautifully. Try a metallic cover-up or something with a fringe detail for that laid-back yet glam vibe.
  • Romantic dinners: For a more polished look, choose a wrap-style dress or a chic off-the-shoulder top to wear over your swimsuit. A simple pair of wedge heels or strappy sandals will elevate the outfit, taking you straight from poolside to dinner without a wardrobe change.

Accessorize to Maximize Your Look

Accessories are a game-changer when it comes to transforming your swimwear from basic to stylish. The right accessories can help you express your personality and elevate your poolside look.

  • Statement sunglasses: A good pair of oversized, trendy sunglasses can add an instant style upgrade, making you look like you’re ready to step out of a fashion magazine.
  • Wide-brimmed hats: I can’t stress enough how a chic hat can change the vibe of an outfit. It not only keeps the sun off your face but also adds an elegant touch. A straw fedora or floppy hat can make you look effortlessly stylish.
  • Jewelry: Don’t be afraid to pile on the accessories. Layered necklaces, chunky bracelets, and even ankle bracelets can add a playful, yet sophisticated element to your look. Just remember, less is more when it comes to daytime. For evening, feel free to go a little bolder.
  • Bags and totes: A beach bag or oversized straw tote is perfect for carrying all your essentials. If you’re heading out for the evening, swap it for a small crossbody or a woven clutch to keep it chic but functional.

Finding the Right Swimsuit

While the cover-up is key, let’s not forget the swimsuit itself. Finding a bathing suit that flatters your body and suits your lifestyle is essential. Orlando’s resort and poolside culture means you’ll want something that’s both stylish and comfortable for all-day wear.

Here are some swimsuit options I recommend based on different body types:

  • For a curvier figure: Look for swimsuits with structured tops or underwire for support. High-waisted bottoms are great for providing coverage and shaping.
  • For athletic builds: Try a one-piece with side cutouts or a bikini with a ruffle detail. These elements can help create curves and add a feminine touch.
  • For a long torso: Opt for a high-neck one-piece or a bikini with a bandeau top. Both styles help balance out your proportions and keep you feeling comfortable while swimming or lounging.

I’ve found that the best swimsuit is one that makes you feel confident, no matter what. After all, confidence is the best accessory anyone can wear.

Embracing Comfort without Compromising Style

Living in Orlando means you’re likely going to spend a lot of time around pools, resorts, and beaches. But just because you’re by the water doesn’t mean you need to sacrifice style for comfort. With the right mix of stylish swimwear, cover-ups, and accessories, you’ll feel fabulous from poolside to party time—without breaking a sweat.

Whether you’re heading to an upscale resort or enjoying a day by the water, remember that the key to looking great is in the details. A perfect cover-up, a flattering swimsuit, and a few well-chosen accessories are all you need to feel stylish and confident in Orlando’s year-round sunshine. So go ahead, dive in, and let your personal style shine through every splash.