Going to a Rooftop Bar? Here’s Exactly What to Wear…

Knowing what to wear to a rooftop bar is one of those things that sounds simple until you’re actually standing in front of your wardrobe trying to figure it out. Most rooftop venues sit somewhere between casual and dressy which makes it genuinely difficult to get the balance right. Too casual and you feel underdressed, too dressed up and you look like you’ve wandered in from a completely different occasion.

The good news is it doesn’t have to be that complicated. A good top, the right trousers or a dress that works for daytime and you’re pretty much there. Whether you’re heading up for bottomless brunch, celebrating a birthday brunch or just making the most of a sunny afternoon with friends, these rooftop bar outfit ideas have got you covered.

And if you want even more brunch inspiration while you’re here, these summer brunch outfits, casual brunch outfits with jeans and casual Sunday brunch outfits are worth a look too.

What to Wear to a Rooftop Bar?

Rooftop bars sit in that sweet spot between casual and dressed up, so smart casual is generally the way to go. These rooftop bar outfit ideas are all about finding that balance: one statement piece a bold top, a printed dress or a great pair of trousers and building around it. It’s also worth bearing in mind that rooftops can get breezy in the evening, so having a blazer or layer you can throw on is never a bad idea. One last thing: if you know you’ll be standing on a rooftop terrace, maybe leave the stilettos at home and opt for a block heel or flat instead.

1. Deep Red Corset, Denim Shorts & Animal Print

Rooftop bar season, and I am obsessed with this combination. A deep red corset top with denim shorts is such a good summer formula. The shorts keep it from feeling too dressed up, but you still look like you actually tried.

The tan leather belt is doing a lot of quiet work here, and the gold lariat necklace is the kind of jewellery that looks expensive but isn’t fussy at all.

The real talking point though, is the accessories. Zebra-print kitten heel sandals and a spotted calf-hair bag brown animal print on brown animal print and it just works. The shared tones stop it from feeling too much and honestly it’s what makes this outfit interesting and different from the rest.

2. Chocolate Halterneck Dress with Neutral Accessories

If the first outfit is for evening rooftop drinks, this one is more of a lazy afternoon vibe, the kind of rooftop where you’re in no rush to be anywhere. The chocolate halterneck mini dress is doing all the heavy lifting here and honestly it doesn’t need much help.

The accessories all lean into the same natural, warm tones which is what makes it feel so cohesive. The straw bucket hat and woven chain bag are very much in the same family, and the tan flip flop heels keep the relaxed feel going without the outfit looking like you just rolled out of bed.

The gold watch and those dark plum and gold drop earrings are the bits that stop it from feeling too casual they add just enough polish to remind you this is still a rooftop bar and not the beach. The oversized brown-tinted aviators finish the whole thing off perfectly.

3. Blue Bralette, Striped Trousers & white Shirt

This one is for the rooftop brunch that turns into afternoon drinks and you’re not quite sure how dressed up to go. Blue striped wide leg trousers and a powder blue bralette is such a good summer combination, and the oversized white shirt layered on top gives you options depending on the weather and the vibe.

If it’s a cooler day, wear the shirt buttoned up and tucked loosely, it looks really sharp against the striped trousers. But if the sun is out and you want to dial things up a little, leave it open and let the bralette do the talking. It completely changes the feel of the outfit without you having to change a single thing.

The accessories add a little razzle dazzle whilst still sticking with the colour pallet. The powder blue shoulder bag echoes the trousers and bralette without being too matchy, and the white flat sandals are the right call here as heels may make this fit feel too formal. The cat eye sunglasses top this outfit off perfectly.

4. Burnt Orange Satin Halterneck, Jeans & Brown Perspex Heels

This is the outfit for when you want to look like you actually made an effort for the rooftop but still feel like yourself. The burnt orange satin halterneck is the kind of top that looks expensive and does most of the work, and tucking it into wide-leg jeans with a gold chain jazzes up the outfit nicely.

What makes this outfit so good is how the warm tones run through every single piece. The tortoiseshell resin earrings, the brown cat eye sunglasses, the brown leather shoulder bag and those brown perspex heels are all speaking the same language and it gives the whole look a really intentional, considered feel.

5. Black and White Print Slip Dress and Black Flat Sandals

You don’t have to wear lots of colour to still look cute at a rooftop bar. This monochrome-printed slip dress is one of those pieces that looks so much more interesting in person than it does on paper. The pattern gives it loads of personality without you having to do anything else.

Keeping everything else in black just makes sense here. The black cat eye sunglasses, leather drawstring bag and flat leather sandals all let the dress be the statement peice.

6. White Blazer, Black Bralette and Cropped Trousers with Silver Accessories

This is the rooftop outfit that works just as well for birthday drinks as it does for somewhere with an actual dress code. The black bralette and cropped black trousers make a strong base, and throwing an oversized white blazer over the top takes it from simple to classy.

The silver accessories are doing a lot here in the best way. The layered silver coin necklace against the black bralette look less plain, and the sculptural silver drop earrings add the finishing touches for jewellery. The sunglasses keep the whole thing feeling sleek rather than overdone.

The silver metallic shoulder bag is such a good choice with this it bridges the white blazer and the silver jewellery in a way that a black or white bag just wouldn’t. And the black kitten heel flip flop sandals are unexpected enough to make the outfit feel current without going full going-out shoe.

And that’s a wrap on these rooftop bar outfit ideas! The most important thing is that you feel good in whatever you choose, whether that’s a printed slip dress and flat sandals or a white blazer and bralette combo. There really is no wrong answer as long as you’re comfortable and feel like yourself.

If you found this helpful, save this post for the next time you’ve got rooftop plans and no idea what to wear.