Kloof Street Cape Town - Coolest Street in Cape Town

It’s the ultimate battle of the Cape Town streets. With a city as trendy and vibrant as the Mother City, its no surprise that her streets are every bit as cool, quirky and one-of-a-kind as the city itself. But which Cape Town street takes the crown? Time to find out! Here are our top 5 coolest streets in Cape Town. All of which are jam-packed with character, hip hangout spots, quirky cafés, a vibrant energy and cool local hidden gems you won’t quite find anywhere else.

#1 Kloof Street

Kloof Street Cape Town Coolest Street in Cape Town
Photo credit: Instagram: @namhla.damoyi

Picking up where Long Street drops off, right in the heart of the vibrant City Bowl, Kloof Street is undoubtedly one of the coolest streets in Cape Town. Dubbed the trendy OG of the Cape Town cool scene, Kloof Street has established itself as one of the most sought-after hotspots for locals and travellers alike. Where you’re guaranteed to have a good time right throughout the day and night. Widely known as the ultimate mecca for foodies, forward-thinkers, trend-setters and artistic enthusiasts, Kloof Street is at the very top of its game.

From cool coffee shops, quirky cafés and artisan hotspots to hip hangouts, trendy bars, laid-back eateries and top-tier restaurants. There truly is something for everyone to enjoy. But besides amazing places to drink and eat, Kloof Street offers way more than meets the eye. You can also find an incredible variety of contemporary art galleries, fashion boutiques, lifestyle centres and interior design stores. Its therefore safe to say that strolling through this cool Cape Town street is an epic adventure filled with tons of surprises and gems along the way.

Some of our coolest Kloof Street spots include: Yours Truly on Kloof; Molten Toffee; Kloof Street House; Hudson’s the Burger Joint; Van Hunks; Bombay Bicycle Club; Black Sheep Restaurant; Café Paradiso; Sushi Box Kloof Street; The Power & The Glory; Tiger’s Milk on Kloof

#2 Bree Street

Bree Street Cape Town Coolest Street in Cape Town
Photo credit: Instagram: @skinnylaminx

Considered the hipster’s paradise of Cape Town, the bustling Bree Street is at the very top of its cool game. And we’re loving every second of it! In addition to Bree Street being one of the coolest streets in Cape Town, it’s also one of the most ‘Instagrammed’ spots in the Mother City. Further adding to its status as being one of the most sought-after hotspots and locations in town. Bree street is a long stretch of road that runs right through the heart of Cape Town’s lively City Bowl. With people travelling from far and wide to experience its vibrant energy, cool laid-back vibe, open-minded perspective and buzzing atmosphere first-hand.

While Bree Street used to be rather timid, with a few shops and organic cafés scattered about. It has blossomed into the ultimate inner-city hub where local artists, creatives, trendsetters forward-thinkers and the movers and shakers of Cape Town collide. But what can you expect from this cool Cape Town street? Bree Street boasts a variety of trendy tapas bars, an effortlessly cool restaurant strip, artisanal beer bars and bakeries, hipster cafés and coffee shops. There’s even an old-school barber shop and an eatery dedicated exclusively to cheese. How cool is that?

But at night is when Bree Street really comes alive! While its buzzing on most nights of the week, it certainly kicks it up a notch on the first Thursday of every month for the famous Cape Town inner-city First Thursday festivities. This is a cherished local event where local art galleries, shops, bars and restaurants stay open much later than usual. And visitors are encouraged to stroll the street on foot, mingle with fellow locals and travellers and truly immerse themselves in the cultural heartbeat of the city. And have tons of fun while doing it of course!

Some of our coolest Bree Street spots include: Clarke’s on Bree; Hank’s Old Irish; Love Thy Neighbour; BOCCA; Arcade; Villa 47; Culture Cheese Club; La Parada; Mother’s Ruin Gin Bar; Skinny Laminx

#3 Loop Street

Loop Street Cape Town Coolest Street in Cape Town
Photo credit: Instagram: @ insideguide | @skinnylegscafe

Loop Street is sassy and sophisticated all while being trendy and laid-back. Undoubtedly making it one of the coolest streets in Cape Town. Wedged right in between the lively and loud Long Street and hip and buzzing Bree Street, Loop Street often flies under the Cape Town cool radar. But, don’t you dare underestimate this cool inner-city street. It’s bound to surprise you in all the best ways.

While Kloof and Bree Street sure knows how to let their hair down and have a good time, Loop Street gives us a look at the more chic and sophisticated side of Cape Town. Boasting more than 5 art galleries showcasing some of South Africa’s best contemporary artists, Loop Street has fast become the place to be for art lovers from all walks of life. But besides it’s cool artistic flair, Loop Street has so much more to offer. From chic and stylish nightclubs featuring trendy décor and world-class DJs to a variety of renowned restaurants, bars, bakeries and cafes catering to a variety of palettes, Loop Street definitely has a whole lot going on.

Some of our coolest Loop Street spots include: Yours Truly on Loop; Homage; The Village Idiot; Marrow; Skinny Legs Luxury Café; 91 Loop; Homage 1862; House of H; Banks Burgers

#4 Hudson Street

Hudson Street Cape Town Coolest Street in Cape Town
Photo credit: Instagram: @ origincoffeesa

De Waterkant is easily known as one of Cape Town’s trendiest neighbourhoods. Boasting a vibrant atmosphere, pockets of historic buildings, fashionable shops, trendy restaurants and cool cafés and coffee shops. In addition to being one of Cape Town’s top foodie hotspots and the ultimate party paradise for locals and travellers alike, De Waterkant is also known as the “pink district” of Cape Town. With its wide variety of gay- and straight-friendly bars and restaurants. The cool Cape Town neighbourhood of De Waterkant is therefore widely celebrated for its open-minded perspective, bold and boisterous approach to life and everyone-is-welcome atmosphere. And right at the centre of it all is one of Cape Town’s coolest streets, Hudson Street!

Home to a super cool bar and restaurant strip, Hudson Street is known to draw quite the crowd. But besides promising a really good time both during the day and night, Hudson Street boasts an artistic flare that’s both sassy and sophisticated. With art lovers and keen creatives making their way to this trendy inner-city street to see what all the artistic hype is about. You can therefore expect to find a few chic cutting-edge galleries, including the new No. 5 on Hudson. Which offers art enthusiasts a contemporary and stylish space to view refined, purposeful art right in the heart of the inner city. This cool Cape Town street therefore has something for everyone to enjoy.

Some of our coolest Hudson Street spots include: The Loading Bay; Origin Coffee Roasting Café; Active Sushi; The Piano Bar; Café Manhattan

#5 Shortmarket Street

Shortmarket Street Cape Town Coolest Street in Cape Town
Photo credit: Instagram: @ thehouseofmachines_cpt

Known as the chic yet edgy hipster of the Mother City cool scene, Shortmarket Street has fast become one of the top must-visit locations in Cape Town. Showcasing the very best combination of Brooklyn edge, Japanese spice, some real London grunt and of course a hefty dose of Cape Town cool, Shortmarket Street offers a little bit of everything. But in the best possible way! Besides being one of the top 5 coolest streets in Cape Town, Shortmarket Street is home to some real culinary gems and sought-after hotspots. Some of which includes the famous Shortmarket Club, the Commissary, HQ and the iconic House of Machines.

Making it the ultimate mecca for foodies and avid food lovers from around the world looking to experience the best of what Cape Town’s culinary scene has to offer. In addition to these world-renowned culinary hotspots, Shortmarket Street also boasts a wide variety and eclectic mix of exciting restaurants, bars, hipster hang-out spots, coffee shops and hidden street-side gems. All just waiting to be explored and experienced by you on your adventure through the vibrant streets of Cape Town.

Some of our coolest Shortmarket Street spots include: The Shortmarket Club; House of Machines (which is a motorbike workshop, men’s apparel shop and much-loved café by day and a hipster cocktail bar by night that has even taken over the streets of Los Angeles); The Commissary; HQ (Headquarters); The Africa Cafe