stylish woman enjoying a rooftop bar

World's best rooftop bars

how to dress for a rooftop bar: a style guide

By Skye Miller

Published: 16 Feb 2025

Let's be honest, rooftop bars. They exude a certain je ne sais quoi, don't they? The city lights twinkling below, the cool night air on your skin, maybe a delicious cocktail in your hand... But before you even think about that perfectly crafted Old Fashioned, there's the small matter of what to wear. I've been to my fair share of rooftop soirees – some stylish successes, and, um, a couple of 'what was I thinking?' moments. So, consider this your cheat sheet to looking effortlessly chic (and staying comfy!) while enjoying those stunning city views. Trust me, your future self will thank you.
woman looking stylish at rooftop bar

woman looking stylish at rooftop bar | Image: Supplied

The Dress Code Decoded: Casual Chic vs. Dressed Up

First things first: let's figure out the vibe. Is it a low-key hangout with friends or a more formal event? Most rooftop bars lean towards 'casual chic' – think upscale comfort. A super tight mini-dress is probably too much. But that awesome jumpsuit? Absolutely! It's about finding that balance between stylish and relaxed. Think about the time of year too – a flowy maxi dress in summer is a great idea; but for a cool autumn evening, layers are key!

Casual Chic: Think stylish jeans (that fit you perfectly!), a cute blouse, or that perfect, not-too-revealing midi dress.

Dressed Up: Think elevated fabrics like silk or velvet, statement jewelry, and heels or stylish boots. But even then, remember comfort is key! You'll be standing for a while.

stylish outfits for rooftop bar

stylish outfits for rooftop bar | Image: Supplied

Fabrics to Embrace (and Avoid)

The fabric you choose can make or break your rooftop experience. Lightweight fabrics are your best friend, especially during warmer months. Think breathable cotton, linen, and silk. Avoid anything too heavy or stiff – you'll be miserable trying to enjoy a drink in a restrictive dress. I once wore a heavy velvet dress to a rooftop bar, and I was sweating profusely the moment I stepped off the elevator! I looked like I had just finished a marathon, not enjoyed a sophisticated cocktail. Don’t be like me!

  • Say Yes To: Linen, cotton, silk, chambray
  • Say No To: Heavy wool, stiff denim, anything overly synthetic (unless its designed for breathability).
Different fabrics for women's outfits

Different fabrics for women's outfits | Image: Supplied

Accessorizing Your Rooftop Look

Accessories are where you can really have fun and express your personal style! A great pair of sunglasses are a must-have, even if it's a bit overcast—they add a touch of mystery and protect your eyes from the setting sun. A statement necklace can elevate a simple dress, while a stylish belt can cinch your waist and make you look instantly more pulled together. Don't forget comfortable shoes; you'll be doing a fair bit of walking and standing! And if there's a slight chill, a stylish blazer or cardigan can be your new best friend; plus, its a great way to add a bit of color to the outfit.

However, don't overdo it. Too many accessories can overwhelm your outfit. Less is often more. Think about one or two key pieces that will really make your outfit shine. And don't forget a purse or clutch that is practical, yet fashionable!

woman accessorizing outfit for rooftop bar

woman accessorizing outfit for rooftop bar | Image: Supplied

Weather-Appropriate Style

Rooftop bars are exposed to the elements, so it's crucial to dress for the weather. In the summer, opt for lightweight and breathable fabrics; layers for the cooler nights is a must-have. If it's windy, avoid anything too loose that will blow all over the place! In the winter, layers are key. A warm coat is essential, plus a stylish scarf that complements your outfit. You're out to have fun; don't let the weather spoil it!

Women wearing outfits in different weather conditions

Women wearing outfits in different weather conditions | Image: Supplied

The Ultimate Rooftop Bar Outfit Formula

Ready for a foolproof formula? Here’s how you can combine these tips to create the perfect outfit:

  1. Choose a comfortable, stylish base: Think a pair of well-fitting jeans, a cute jumpsuit, or a flattering dress.
  2. Add some personality: A statement necklace or earrings make a perfect pop of personality.
  3. Layer up (or down): A cardigan, blazer, or light jacket will make sure you're prepared for anything.
  4. Shoe game strong: Stylish and COMFORTABLE shoes are a must.
  5. Practical accessories: Bag, sunglasses (don't forget your sunglasses!), and a little touch of your own flavor.
So there you have it! My guide to dressing for a rooftop bar. Remember, the most important thing is to feel confident and comfortable. The views are amazing, but your smile is even better. Now go out there and enjoy yourself – you deserve it! What are your favorite rooftop bar outfits? Share in the comments below!

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