Orlando might be known for its theme parks, but when the sun goes down, the city transforms into a hotspot for date nights of all kinds. Whether you’re headed to a casual dinner in Winter Park, a sunset boat ride on Lake Eola, or a more upscale evening at one of the city’s chic rooftop bars, Orlando has a little something for every type of date.
With over a decade of experience helping women dress for all kinds of events, I’ve seen firsthand how the right outfit can elevate any night out. The goal is always to feel comfortable and confident, but most importantly, to pick something that fits the vibe of the evening. I’ve pulled together five stylish outfit ideas for different types of dates—because who says you can’t have fun while looking fabulous?
Casual but Chic: Dinner and Drinks on a Laid-Back Date
For a more casual date—think dinner at a local restaurant or grabbing drinks at a bar in the city—you want to strike that balance between laid-back and stylish. You don’t have to overthink this, but it’s always nice to show up looking put together.
- A Flowy Midi Dress: Midi dresses are the perfect choice for a laid-back dinner. They’re easy to wear, and they work for almost any setting. Whether you go for a floral print or a solid color, the midi length keeps things casual, while the right fabric can elevate the look. Pair it with cute sandals or ankle boots, and you’re good to go.
- Tailored Pants and a Chic Top: If you’re not feeling a dress, try a pair of high-waisted, tailored pants. These are comfortable and flattering, plus they allow you to move around easily. Tuck in a simple blouse or a trendy top with fun details (like ruffles or puffed sleeves) to add a touch of personality. Slip on some loafers or block heels for an effortlessly chic look.
Cozy & Comfortable: The Perfect Movie Night Look
Not every date needs to be fancy, and a relaxed movie night is a great way to spend time together. Still, you want to feel cozy without slipping into full-on loungewear. Here’s a look that keeps it stylish, but still comfy.
- A Soft Sweater and Jeans: A cozy knit sweater paired with your favorite pair of jeans never goes out of style. If you’re going for a more laid-back vibe, opt for a chunky knit or a sweater with interesting textures or patterns. You can easily roll up the sleeves or tuck in the front to give it a more stylish feel. Pair it with your go-to jeans—skinny, wide-leg, or straight-cut—and comfy sneakers or ankle boots.
- Joggers and a Fitted Top: If you love the jogger trend (who doesn’t?), these are a great way to combine comfort and style. A fitted, high-neck top or a tucked-in T-shirt balances the relaxed feel of the joggers, and you can throw on a denim jacket or cardigan for extra warmth if needed. Toss on some slides or sneakers, and you’re ready for a cozy date in style.
Semi-Formal: Dinner and Dancing Downtown
When you’re stepping it up a notch, like going out for dinner and dancing, you’ll want to look polished but still have fun with your outfit. Orlando’s nightlife scene is vibrant, and you don’t want to be underdressed or overdone.
- A Little Black Dress (LBD): You really can’t go wrong with the classic LBD, especially for a night out where you might hit a fancy restaurant followed by drinks and dancing. Keep it simple, or go for something with a little flair, like a wrap dress or one with interesting details (think: lace, sequins, or a plunging neckline). Pair it with heels or statement flats, depending on how much comfort you want to trade off for style. Add a pop of color with a fun clutch or bold jewelry.
- Maxi Skirt and Fitted Top: If you’re not feeling a dress, a flowy maxi skirt paired with a fitted top can look super chic and still be comfortable for a night out. I personally love a satin or silk maxi for an added touch of luxury. The fitted top keeps the outfit balanced, and you can add a pair of strappy heels to amp up the look.
Upscale and Elegant: Fine Dining or Rooftop Bars
When you’re heading to a fine dining spot or a posh rooftop bar, it’s time to pull out the stops. You don’t need to go full-on cocktail dress, but you’ll want to dress in a way that feels elevated but still comfortable enough to move around.
- Tailored Jumpsuit: If you’re not in the mood for a dress, a tailored jumpsuit is the perfect alternative. It’s sleek, chic, and easy to wear. Look for one in a fabric like silk, satin, or a heavy crepe. Whether it’s strapless, off-the-shoulder, or with a high neckline, a jumpsuit can be just as striking as a dress, and it’s a real head-turner for upscale events.
- Sleek Midi Skirt and Top: If a jumpsuit feels too daring, a high-waisted midi skirt with a tucked-in blouse is an elegant option. Satin or silk midi skirts are especially great for formal events, and pairing them with a fitted, structured top will give the outfit balance. For shoes, a pair of elegant pointed-toe heels or mules will complete the sophisticated look.
Trendy and Fun: Theme Park Day Date
Orlando’s theme parks are a huge draw for visitors, but that doesn’t mean you can’t look stylish while riding roller coasters and exploring the parks. The goal is comfort and practicality without sacrificing style.
- Chic Romper: A romper is a fantastic go-to for a theme park day. It’s easy to move in, keeps you cool, and still looks stylish. Choose one with a fun print or a simple, flattering cut that can easily go from day to night. Pair it with comfortable sneakers or espadrilles, and don’t forget your sunscreen!
- Sporty Vibes with a Twist: If you’re more of a pants person, try a pair of comfortable, cropped wide-leg pants paired with a casual tank or T-shirt. Add a lightweight jacket in case it gets chilly in the evening. Sporty sneakers or slip-on sandals will keep you moving comfortably throughout the day.
A Date for Every Style
Orlando offers a variety of date night settings, from casual movie nights to more formal rooftop outings. The beauty of choosing the right outfits is that you can feel comfortable while also showcasing your personal style, no matter what the evening holds. From simple, breezy dresses to more tailored pieces, there’s an outfit that’s perfect for every occasion in Orlando. Dressing for your date should be just as fun as the date itself—after all, it’s the confidence you wear that makes any outfit truly shine.