Orlando isn’t just about theme parks and sunny weather—it’s a place where fashion blends seamlessly with a laid-back, active lifestyle. Whether you’re spending the day at a trendy brunch spot, enjoying an afternoon poolside, or heading to an evening cocktail party, dressing for Orlando is all about comfort, style, and versatility. Having lived in the fashion world for a decade, I’ve seen first-hand how easy it is to look great in Orlando while keeping things simple and breezy. Here’s how to build a wardrobe that fits the vibrant lifestyle of this city.
Stay Cool Without Sacrificing Style
Living in Orlando means dealing with heat and humidity, especially in the summer months. But don’t let that stop you from looking your best. The trick is to wear clothes that are breathable, light, and allow you to move freely. No one wants to feel weighed down by heavy fabrics when it’s 90 degrees out!
- Lightweight Dresses: A classic summer go-to for me is a cotton or linen dress. These fabrics allow air to flow and keep you cool, even during the hottest days. Whether you’re brunching with friends at a cute café or strolling through one of Orlando’s many outdoor markets, a flowy midi or a sleeveless maxi dress gives you both comfort and style.
- Chic Rompers and Jumpsuits: Rompers are perfect for Orlando’s active lifestyle. They’re easy to move around in and look put together without trying too hard. I love how versatile they are—you can wear them to a poolside party or even dress them up for an evening out. Look for fun prints or solid colors and pair with simple accessories like flat sandals or wedges.
- Tailored Shorts & Tops: When it’s too hot for jeans but you still want to look polished, go for tailored shorts. They offer the structure of pants but keep you cool. Pair them with a button-up blouse or a breezy off-the-shoulder top for a stylish, summer-ready look. Add a pair of sneakers for an easygoing vibe or block heels if you’re stepping it up a notch.
Poolside Vibes: Fashion Meets Fun in the Sun
Orlando’s pool parties and resort-style settings demand outfits that are both fun and practical. When you’re lounging by the pool or attending a casual poolside event, your outfit should be effortless but still fashionable.
- Cover-ups that Turn Heads: A cute cover-up is a must when you’re heading to the pool. I suggest looking for lightweight kaftans, tunics, or oversized shirts. These give you the coverage you want while still looking stylish enough to take a few poolside photos. A colorful sarong or a woven beach bag can add just the right amount of flair.
- Breezy Swimsuits: When it comes to swimwear in Orlando, I recommend swimsuits that can double as part of your outfit. High-waisted bikini bottoms with a matching top or a sleek one-piece with a simple, chic design are always in style. Throw on a stylish pair of sunglasses, and you’re good to go.
- Flip-flops and Slides: It might seem like a small detail, but the right pair of sandals can elevate your poolside look. Go for a pair of sleek, minimal flip-flops or comfy slides—both practical and chic, perfect for a day in the sun.
Brunch and Beyond: Effortlessly Stylish Daywear
Orlando has no shortage of trendy brunch spots, from rooftop cafes to cozy eateries. When you’re planning your brunch look, think casual but put together. I’ve found that accessories and layering can elevate even the simplest outfits.
- Flowy Tops & High-Waisted Pants: A flowy blouse with a pair of high-waisted, wide-legged trousers is one of my favorite combos for brunch. The top can be tucked in or left loose, depending on the vibe, and the pants add structure while still being comfortable. It’s a chic look that’s easy to throw on without overthinking.
- Casual Dresses with Sneakers: A cute, casual dress paired with white sneakers is a look I see often in Orlando, and for good reason—it’s stylish, comfortable, and perfect for a day of exploring or grabbing mimosas. Whether it’s a floral midi or a simple knit dress, the sneakers give it that relaxed, everyday feel.
- Denim with Style: Denim is a wardrobe staple in Orlando. A pair of high-rise jeans paired with a simple tucked-in blouse or graphic tee is a go-to for a casual yet stylish look. Throw on a pair of chunky heels or even trendy flat sandals to make it more polished.
Evening Out: Making the Transition from Day to Night
When the sun sets in Orlando, the city comes alive. Whether you’re headed to a trendy rooftop bar or an elegant dinner, you’ll need to transition from laid-back daywear to something a bit more polished.
- Maxi Dresses for Dinner: A flowy, sophisticated maxi dress is perfect for evening events. Whether it’s a simple black dress with statement jewelry or a patterned number, you’ll feel both comfortable and elegant. Just add a pair of heels and you’re set for a stylish dinner at one of Orlando’s finer restaurants.
- Stylish Jumpsuits: I can’t tell you how many times a well-fitting jumpsuit has saved the day for evening events. A jumpsuit with a cinched waist and wide-leg pants is comfortable enough for casual outings but elevated enough for upscale dinners or drinks. Pair with bold earrings and a clutch to finish the look.
- Chic Blazers and Tailored Pants: If you need to dress up your look, opt for a fitted blazer with tailored pants or a pencil skirt. A nice blazer can elevate even a simple t-shirt or blouse, making it perfect for an evening at a cocktail bar or a formal gathering. Add a pair of heeled sandals, and you’ll look effortlessly chic.
Versatile Accessories: The Key to Orlando Style
Accessories can really make or break your look in Orlando. The key is to keep it simple, but make sure it fits the active, vibrant lifestyle of the city.
- Sunglasses: A good pair of sunglasses can elevate any outfit. Look for a pair of oversized frames or classic aviators to protect your eyes while adding an instant touch of glamour.
- Crossbody Bags & Clutches: A crossbody bag is perfect for daytime wear—easy to carry and functional. For evening events, swap it out for a stylish clutch or small handbag that adds that extra flair to your outfit.
- Layered Jewelry: When it comes to jewelry, layering is always a good idea. Stackable rings, layered necklaces, and dainty bracelets work for both day and night. I always recommend keeping it simple but chic.
Dressing for an Active Lifestyle
Orlando isn’t just about looking good—it’s about doing. Whether you’re running errands or enjoying an outdoor adventure, your clothes need to move with you. Think easy, comfy, and practical, while still looking put-together.
- Athleisure: Orlando is all about the athleisure trend. A pair of high-waisted leggings with a sporty top or hoodie can easily take you from a morning workout to a post-workout brunch with friends. Don’t forget to add stylish sneakers—comfortable yet chic.
- Lightweight Jackets: For early morning jogs or evening walks, a lightweight, packable jacket can be your best friend. Look for jackets that can easily be stowed in your bag or tied around your waist. A cropped jacket or bomber can add a sporty vibe to any outfit.
Dressing for Life in Orlando
When it comes down to it, dressing for Orlando’s lifestyle is all about mixing comfort with a bit of style. The key is to choose outfits that reflect the laid-back, active nature of the city while still allowing you to look great and feel confident. Whether you’re brunching with friends, lounging poolside, or attending an evening event, the goal is to have fun with fashion. Keep it simple, breathable, and always add those personal touches that make your outfit uniquely yours.