Coolest Street in Cape Town

By Bianca Bunge.

It’s time to take to the Cape Town streets for the ultimate battle royal, who will claim the coveted title of coolest street in Cape Town? Who is really at the top of their Cape Town cool game? It’s time to find out once and for all! There is no denying the fact that it certainly is, and will continue to be, a hot topic of debate amongst locals and tourists alike. But in an exciting, dynamic and influential city like Cape Town, how can it not be? Known for her unapologetic beauty, bold sense of style and yearning to colour outside the lines, the Mother City is all that and a bag of chips when it comes to her ‘cool factor’. Home to a variety of hip hangout spots, trendy neighbourhoods, a vibrant art scene, and of course, cool Cape Town streets, you can’t help but want to discover and explore everything she has to offer. So, join us as we stroll down some of the Mother City’s coolest streets in our quest to rank our top Cape Town cool kid, who will earn the coveted cool crown? There’s only one way to find out, let the countdown commence!

6. Harrington Street: The cultishly cool rising star of the East City Precinct!


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If cool creative hubs, cutting-edge galleries, chic cafes, edgy dive bars and hipster hangout spots is your vibe, Harrington Street is where you’ll find your tribe! And while Cape Town’s Harrington Street might fly under the radar with pure counter-culture intent, its rocking its vintage t-shirt, worn boots and skinnies and loving every hipster second of it. Although Harrington Street may now be hip, happening and on the Cape Town high rise, this wasn’t always the case. Let’s be honest, in the past no one would have blamed you for giving Harrington Street a hard pass, but after some hard grind and a turn of events this East City Precinct has finally made its mark. And it’s certainly giving other streets a good go for the Cape Town cool crown! To some people’s surprise, Harrington has undergone a profound transformation in recent years, so much so that the area around Harrington Street and District 6 is almost unrecognizable. Home to an endless array of cool coffee shops, hip hangouts, trending restaurants, viby burger joints, a variety of must-visit shops and popular organic and vegan eateries, this cool Cape Town street is filled with some truly epic Harrington hipsters that’s bound to knock your socks off, especially if they’re patterned and have cool graphics!

Our favourite Harrington Street spots:
  • Lefty’s: This hip, low-key Harrington Street spot is a bar, restaurant and cool hangout spot all in one! It’s easy going atmosphere, cool vibe and delicious food will definitely have you coming back for more.
  • Surfarosa: This edgy neighbourhood bar might serve a bit of grunt and street side edge with their drinks, bit you’ll be eating it up in no time! Its rustic interior is really cool too!
  • New York Bagel: Known as the best bagel spot on the continent, we challenge you to disagree after just one bite! Specialising in traditional boiled and baked New York style bagels, this cool Harrington Street bagel hotspot is sure to win over your heart.

5. Hudson Street: But first… Coffee!!


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Easily known as one of the trendiest neighbourhoods in Cape Town, De Waterkant is known for its vibrant atmosphere, stylish pockets of historic buildings, fashionable shops, vibey restaurants and cool hangouts and coffee shops. But besides being any foodie’s dream come true, as well as the ultimate party paradise, it is also affectionately known as the “pink district” with its abundance of gay- and straight-friendly bars and restaurants. De Waterkant is therefore internationally renowned and celebrated for its open-minded attitude, alternative approach to life and bold unapologetic nature to colour outside of the lines, and we LOVE it! And situated right in the heart and soul of this cool Cape Town neighbourhood is the ever-trendy Hudson Street. Besides a super cool bar and restaurant strip, Hudson Street also has an artistic flare that’s both sassy and sophisticated. Home to a few chic cutting-edge galleries, including the new No. 5 on Hudson, it offers a contemporary and tasteful space to view refined, purposeful art and fine objects in the inner city of Cape Town.

Our favourite Hudson Street spots:
  • Loading Bay: Situated in the culturally rich and diverse district of De Waterkant, the Loading Bay offers a space for exploration and curiosity. This cool Hudson Street space is an eatery, selected menswear and Aēsop Skin care shop, talk about multi-functional! It is also committed to an ethical, conscious movement and seasonal and fresh is what they’re all about!
  • Origin Coffee: In Cape Town coffee is culture & Origin coffee is certainly adding some extra fire to the Cape Town coffee flame. Situated in a historic brickhouse and courtyard, Origin Coffee is also one of South Africa’s first artisan coffee roasters. This super cool laid-back café and barista school allows you to taste and experience quality roasted coffee from around the world right here in the trendy Hudson Street.

4. Loop Street: Sassy, sophisticated & soaring under the Cape Town cool radar


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Wedged right in between the lively loud Long Street and cool trendsetting Bree Street, many consider Loop Street to be suffering from a heavy-dose of middle-child syndrome. But don’t you dare underestimate this cool Cape Town street, it’s about to surprise you in the very best way! Loop Street, that runs parallel to Long Street, has been relatively unassuming all these years, quietly plotting it’s rise to the top one lively nightclub, trendy art gallery and cool restaurant at a time. And while it might not be at the very top of the Cape Town cool scene just yet, it’s certainly making us sit up and take note.  Boasting more than 5 art galleries showcasing some of South Africa’s best contemporary artists, chic and stylish nightclubs featuring stunning décor and world-class DJs, as well as a variety of superb restaurants, bars, bakeries and cafes catering to a variety of palettes, Loop Street certainly has something for everyone.

Our favourite Loop Street spots:
  • Homage: Housed in a heritage building dating back to 1862 this Loop Street hotspot is every bit as cool as it is authentic! This sophisticated yet quirky eatery is all about hearty haute cuisine and the delicious simplicity of South African fan-favourites.
  • Yours Truly: Yours Truly on Loop Street is the newest edition to the Yours Truly family and has all the same cool vibes as it’s Kloof Street counterpart. And yes, Yours Truly really is every bit as cool as people say it is
  • Village Idiot: The bohemian to our rhapsody! The Village idiot is a cool bohemian paradise with a touch of local South African flair situated right in the heart of Cape Town’s inner city. This vintage neighbourhood restaurant and bar is trendy and viby and fully embraces South African braai culture and we LOVE it!

3. Shortmarket Street: The chic yet edgy hipster on the Cape Town block


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While Bree & Kloof Street might be known as Cape Town’s current headliners among locals and tourists alike, Shortmarket Street doesn’t mind one bit! In fact, this edgy hipster is so confident in its Cape Town cool factor that it fully embraces doing its thing and forging the trendy trail ahead in its own authentic way. With a bit of Brooklyn edge, chic Japanese spice, some real London grunt and of course a hefty dose of Cape Town cool, Shortmarket Street is a little bit of everything, but in the most authentic and captivating way. This edgy Cape Town street also boasts some real heavy-hitters that’s bound to sky-rocket it to the top of every Cape Town local or traveller passing through’s Mother City to-do list. Boasting 4 of the Cape Town cool top dogs the Shortmarket Club, the Commissary, HQ and the iconic House of Machines, you better know Shortmarket is here to stay in the Top 3 Cool streets of Cape Town. Besides these 4 Mother City headliner, Shortmarket also boasts an eclectic mix of exciting restaurants, bars, hipster hang-out spots, coffee shops and hidden street-side gems just waiting to be explored by you.

Our favourite Shortmarket Street spots:
  • House of Machines: The iconic and world-renowned 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 was such a massive Shortmarket Street hit that it has now taken over the streets of Los Angeles too! How epic!
  • HQ: A parisian-inspired steakhouse/bar/lounge all rolled into one situated right in the heart of Heritage Square. This Shortmarket Street heavy-hitter really is a breath of fresh air in the dining world and is guaranteed to take your dining experience to the next level!
  • Shortmarket Club: The old-world, Gatsby-esque charm of the Shortmarket club is sure to knock your socks off! Whether it’s the cool leather booths, swanky yet chic and edgy ambiance or chef Wesley Randle’s stellar food, the Shortmarket Club really is worth all the rage and praise it’s getting!

2. Bree Street: Cape Town’s hippest Street!


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Since Bree Street made its introduction onto the Cape Town cool scene, it’s been crushing the competition and taking names every chance it gets. Bree Street is undoubtedly considered as the current reigning champ of cool in the eyes of many Cape Town locals, and with really good reason too! Home to an old-school barber shop, a variety of trendy tapas bars, an effortlessly cool restaurant strip, artisanal beer bars and bakeries, hipster café’s and coffee shops, and even an eatery dedicated exclusively to cheese, and that’s merely scratching the Bree Street surface. Yes, Bree Street is jam-packed and trending and its hipster cool factor is off the charts! There’s a reason why it’s one of the most ‘Instagrammed’ spots in the Mother City, and why you should get it on your feed straight away.

Our favourite 3 Bree Street spots:
  • Clarke’s: One of the original hipster haunts in Cape Town’s inner city. Clarke’s has become well known for their epic burgers, all-day breakfasts, awesome cocktails & jam-packed, flavour-filled menu.
  • Hail Pizza: The new kid on the Cape Town pizza block! Their mouth-watering combinations and BOLD flavours are sure to win over your pizza loving heart in seconds! Tucked inside the ever-popular Clarke’s on Bree Street means it’s also scoring plenty of cool points and trendy trail-blazing status amongst locals and tourists alike.
  • Hanks/Love Thy Neighbour: A cool Bree Street eatery that’s bound to knock your socks of with their delicious Mediterranean food!

1. Kloof Street: The trendy OG of the Cape Town cool scene & reigning cool kid on the block!


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Before Bree Street was even a twinkle in the eyes of artisan lovers at heart, Kloof Street was thriving, thrilling and the trending trailblazer of the Cape Town cool scene. And to be honest, it really still is! Picking up where Long Street drops off, Kloof Street is situated right in the heart of the vibrant city bowl and truly is the ultimate mecca for foodies, forward-thinkers, trend-setters, artistic enthusiasts and lovers of all things cool and captivating! While Kloof Street is certainly home to an extensive variety of trendy hangouts, cool coffee shops, charming café’s, out-of-the-box eateries, artisan hotspots and iconic award-winning restaurants, it also boasts a variety of leading art galleries, fashion boutiques, interior design shops, a thriving lifestyle centre and much more. Proving that the ever-trendy, always-cool Kloof Street is way more than meets the eye.

Our favourite 3 Kloof 3 spots:
  • Kloof Street House: An enigmatic dining experience inside an amazing Victorian house. But this grand old dame is way more than just a restaurant, it is a collection of interesting rooms and spaces, each bursting with a character of its own and it’s definitely worth every second of exploring!
  • Yours Truly: This cool Kloof Street café is by far one of Cape Town’s favourite hangouts! Café by day and trendy beer garden by night, Yours Truly is one Kloof Street gem that boasts way more than meets the eye, and it’s bound to surprize you in all the right ways!
  • Molten Toffee: If the name isn’t enough to get you hooked the cool vibe, GREAT coffee and ‘everyone is welcome’ atmosphere of this trendy Kloof Street coffee shop sure will! Plus, the music selection is epic too!

As Kloof Street is certainly our coolest kid on the Cape Town block, these are the streets of the Mother City after all, and that means things can change on a dime. Plus, the Mother City wouldn’t be her bold, unapologetic and dynamic self if she didn’t keep things interesting, now would she? But regardless of how long the Kloof Street cool reign will be, one thing is for certain, the Cape Town cool factor is alive & kicking and filling the streets of Cape Town one hip hangout, artisan bakery, quirky gallery and trendy restaurant at a time and we’re enjoying every second of the epic ride, and so should you!

By Biance Bunge