When it comes to luxury, Orlando is no stranger to providing world-class resorts that make you feel like you’re stepping into a different world. Whether you’re booking a stay at one of the city’s upscale hotels or spending the day poolside at a swanky resort, what you wear can set the tone for your experience. As someone who’s spent years helping women style everything from casual weekend looks to elevated evening outfits, I’ve seen how the right resort wardrobe can make all the difference when it comes to blending comfort and sophistication.
Orlando’s luxury hotels offer a variety of settings—from poolside relaxation to elegant rooftop bars. The key is balancing the laid-back vibes of vacation wear with the elevated standards that these resorts often have. You want to look chic but still feel relaxed enough to enjoy your time. So let’s dive into how to master that effortless resort style and make your stay even more unforgettable.
Light Layers for Comfort and Style
Resorts in Orlando tend to lean on the warmer side, but that doesn’t mean you won’t need a little something to throw over your swimsuit or chic dress. The evenings can cool down a bit, and you’ll want to be prepared while still looking pulled together.
- Flowy Cover-Ups: A sheer, flowy cover-up is one of the best options for days spent by the pool. Opt for one in a lightweight fabric, like cotton or chiffon, so it’s breathable but still adds a touch of style. You can choose from kaftans, kimono-style wraps, or even a relaxed, oversized shirt that doubles as a cover-up and a lightweight jacket when you’re lounging poolside. These can easily transition from day to night when paired with a sleek swimsuit underneath or a chic dress for evening drinks.
- Light Sweaters and Cardigans: For cooler evenings or mornings when you’re heading to a brunch spot, throw on a lightweight cashmere or cotton sweater. Keep the look fresh and airy by choosing a piece with interesting details like wide sleeves or a tie waist. A long cardigan works well too, especially in neutral tones, and you can style it effortlessly over a tank top or a simple sundress.
Comfortable Yet Elevated Footwear
When you’re staying at a luxury resort, the last thing you want is to be uncomfortable in your shoes. Whether you’re walking through the resort grounds or heading to dinner, comfort and style need to come together. But that doesn’t mean you have to sacrifice elegance.
- Espadrilles: I’m a huge fan of espadrilles for resort wear. They’re comfortable enough for a day of walking, yet chic enough to dress up a simple outfit. The canvas or leather versions are versatile enough to wear with everything from maxi dresses to tailored pants. Plus, the woven sole gives them that breezy, vacation-ready look.
- Sandals with Style: When it’s hot outside, you’ll need sandals that offer both style and support. Look for options that are simple but elevated—think flat slides with a bit of metallic detailing or a pair of gladiator sandals that are easy to walk in. Strappy sandals with a slight heel are also perfect for dinner by the water or for a night out, offering just the right amount of sophistication without feeling overdone.
- Chic Sneakers: Sneakers have made their way into resort fashion, and I’m all for it. A sleek, minimalist sneaker can pair well with a dress or pants, especially if you’re headed out for a casual lunch or exploring the resort grounds. White sneakers are a timeless choice, but feel free to experiment with metallics or soft pastels to add a bit of personality to your outfit.
Effortless Dresses That Work All Day Long
When it comes to packing for a resort stay in Orlando, you can’t go wrong with a few staple dresses. Dresses are simple, versatile, and they’re perfect for the easy, breezy vibe that comes with vacation life.
- Maxi Dresses: A flowy maxi dress is always a good idea. Choose a style in a lightweight fabric like linen or cotton, and pick a style with a relaxed silhouette. A tie-waist design or a dress with a bit of drape adds that luxe feel without being fussy. These dresses can easily go from daytime casual to dinner-ready with the right accessories.
- Sundresses: For poolside days and casual dinners, sundresses are a must-have. Go for something that feels breezy—think light fabrics, colorful prints, and flowy cuts. Whether it’s a simple tank dress or one with a halter neckline, the key is comfort with a touch of style. Pair it with a sunhat and sunglasses during the day, and switch to wedges or sandals when heading out for the evening.
- Shift Dresses: A simple, tailored shift dress is a great go-to when you need something a little more polished. Whether you’re going to brunch or a resort-sponsored event, these dresses are flattering on almost any body type and give off a polished vibe. Look for details like ruffles or asymmetrical hems for a modern twist.
Chic Swimwear for Poolside Glam
You can’t talk resort style without mentioning swimwear. Orlando’s top resorts often boast stunning pool areas, and you’ll want swimwear that makes you feel confident, chic, and comfortable. But the key here is that your swimwear can double as daywear if styled correctly.
- One-Piece Wonders: A stylish one-piece swimsuit is not only practical for swimming but also doubles as a body-hugging bodysuit under a skirt or pair of shorts for a casual, beachy look. Look for options with trendy details like cutouts, high necklines, or asymmetrical straps. Pair them with a pair of high-waisted shorts or a sarong for a complete outfit when you’re not in the water.
- Bikinis with a Twist: If you’re a fan of bikinis, go for something that feels unique. A bikini with a fun print, a metallic finish, or subtle details like tassels or crochet can make all the difference. Pair it with an oversized, sheer cover-up and some statement sunglasses, and you’ve got an outfit that’s perfect for poolside lounging and drinks by the bar.
- Swim Dresses: If you prefer a little extra coverage, a swim dress can be both flattering and stylish. Choose one with a structured top and a soft, flowing skirt for a more feminine look. These can easily transition from poolside to lunch at the resort restaurant, especially when paired with sandals or slides.
Accessories That Complete the Look
The right accessories are essential for tying your resort outfits together. They can add personal flair, elevate your look, and make your outfit feel polished. When you’re in a place like Orlando’s luxury resorts, where the setting is as important as the event, accessories are the perfect finishing touch.
- Wide-Brimmed Hats: A stylish, wide-brimmed hat is not only practical for protecting your skin from the sun but also adds a high-fashion touch to any resort outfit. Go for a neutral-toned straw hat or something with a colorful ribbon for a bit of personality.
- Sunglasses: Nothing says vacation style quite like a pair of statement sunglasses. Whether you prefer oversized, aviator, or cat-eye styles, a good pair of sunglasses will always add a touch of glamour. They’re practical for the sunny Orlando weather, and they instantly elevate any outfit.
- Tote Bags: A spacious tote bag is essential for carrying your sunscreen, pool essentials, and everything else you need for a day out. Look for a stylish, structured tote in a neutral shade that complements your outfit, or go for a fun, printed beach bag if you’re feeling playful.
Living the Resort Life
Dressing for Orlando’s luxury resorts is all about embracing the relaxed yet sophisticated vibe. The goal is to stay cool, comfortable, and chic—whether you’re lounging by the pool, enjoying a gourmet meal, or soaking up the atmosphere of your luxurious surroundings. Resort style isn’t about wearing something fussy; it’s about choosing pieces that flow, breathe, and fit into the laid-back glamour of Orlando. So, whether you’re sipping cocktails by the pool or dining in style, the right outfit will ensure you do it all with effortless flair.