For fashion enthusiasts, the thrill of discovering new trends is not limited to the high streets of international cities like London, Paris, Milan, and New York. In recent years, cities like Austin, Miami, and Los Angeles have been catching up to their New York contemporary, carving out a fashion designation the new younger consumer craves: a blend of upscale and upcycled fashion retailers now popping up on U.S. cool fashionable streets.

From millennials to early adopter generations, fashion is a form of self-expression that aligns with their distinct personalities and intrinsic value systems. They will likely shop a blend of pop-ups and boutique brands from up-and-coming designers, streetwear influencers, and thrift vintage stores.

Upcycled luxury fashion, a trend that has tipped the scales with young consumers, involves repurposing high-end fashion items to create new, unique pieces. This sustainable fashion approach reduces waste and allows consumers to mix and match brands and styles. This trend has launched the U.S. secondhand apparel market into supergrowth–7X faster than the broader retail clothing market last year, reaching $43 billion.

Where to Shop Now

This feature delves into Time Out’s Coolest Street Report, a comprehensive ranking of thirty hip and cool city streets. Unsurprisingly, the hip cities cited include metropolitan hubs like Los Angeles, New York City, Chicago, Miami, and Austin, areas known to be populous and critical economic hubs to their corresponding states. These cities, known for their rich and diverse cultures and distinct creative vibes, have had their fair share of struggles in recent years, but they are well-positioned for growth.

The five U.S. streets that topped the list may differ from what you expect: East Eleventh Street in Austin, Fifth Avenue in Park Slope, New York City, East Third Street in Los Angeles, Eighteenth Street in Chicago, and the Miracle Mile in Miami. We consulted fashion and commercial real estate experts to weigh in on the rankings, and the popular opinions may surprise you.

The Other Fifth Avenue in NYC

Park Slope, Brooklyn, known for its tree-lined streets and historic brownstones, experienced a tourism decline and resident exodus during the pandemic. Still, new housing developments are attracting residents back, and the area is on an upward trajectory. This year, the neighborhood, which represents nearly 8% of Brooklyn’s 2.6 million population, has seen a consistent rebound in visitor numbers since 2023.

“It’s not a far cry for the new generation of shoppers to consider the Other Fifth Avenue one of the places to grab their fashion looks with the number of thrift shops and boutiques block to block,” shares stylist Jeffrey Ampratwum, also an adjunct faculty member at the Fashion Institute of Technology (FIT) in New York. “The element of ‘cool’ in NYC can be subjective, as up-and-coming fashion brands pop up in retail areas from the East Village and Soho to Fordham Road in the Bronx to attract the city’s diverse fashion enthusiasts.”

Los Angeles Arts District

“The pandemic has taken a toll on almost every sector of Downtown Los Angeles, but East 3rd Street, one of the only walkable streets in the Arts District, remains extremely strong. This unique street draws a global audience not affected by the nearby office vacancy in Downtown L.A.,” said Gabe Kadosh, Vice President of Colliers International in Los Angeles. The total number of visitors to Downtown L.A.’s Arts District significantly increased in 2023, jumping to 2,700,000 from 1,900,000 in 2022, a growth of 42.11%. Visitors and residents of East Third Street enjoy a thriving neighborhood with diverse shops, markets, restaurants, and bars. A haven for commuters and folks working from home, the area boasts plenty of art galleries and dog parks within walking distance and easy access to public transit via the Little Tokyo/Arts District Station.

18th and Pilsen in Chicago

“Eighteenth Street in Pilsen is an emerging retail real estate location surrounded by eclectic restaurants, art shops, boutiques and event spaces. Retailers like the urban feel you get when walking the streets, and attractions like the Pilsen Art Walk and Pilsen Fest draw people to the area to enjoy the neighborhood’s vibrant atmosphere and community spirit,” shares Chris Irwin, Senior Vice President of Colliers in Chicago. Home to the Chicago Arts District, 18th and Pilsen is a walker’s paradise under gentrification. With household incomes holding steady at $73,000 there is an increased potential for housing developments as the neighborhood becomes more popular.

Miracle Mile in Miami

The Miracle Mile/Coral Gables area has seen a significant boost in restaurant sales post-pandemic, a trend set to continue. This surge is attributed to an influx of people moving to South Florida from all over the country and South America. While sales peaked in 2022 and slightly declined in 2023, they have stabilized, remaining well above national averages. The future of Miracle Mile looks promising, with the addition of new multifamily projects and the continuous evolution of the street tenant mix, bringing in new and exciting concepts.” – Steven Henenfeld, Executive Vice President of Colliers, in Miami. The Miracle Mile will welcome a 41,981 square feet Apple Store later this year, a nod to the retail corridor’s cache and the buying power of 3M tourists visiting each year.

East Eleventh Street in Austin

East Eleventh Street’s vibrant community, steeped in historic African-American culture, has been the focus of a decades-long revitalization effort. The district has undergone organic growth, initiated by the success of Franklin BBQ and other forerunners in the arts, food and retail space. Although some locals and fans of Austin are on the fence about TimeOut’s recognition of East Eleventh Street’s cool factor, the area has a budding cultural cache. With the highest concentration of food trucks to rival South Congress, it is making its mark as the must-visit neighborhood. Austin’s tourism has fluctuated recently, with its most significant increase of 16.32% in 2021, 14.87% in 2022, and a slight decrease in 2023. Despite that, Austin is returning to pre-pandemic visitation, driven mainly by events like SXSW, the CMT Music Awards, Free Week, and the Texas Book Festival, generating 68,190 jobs and $750 million in travel tax revenue.


Some argue that what makes a corridor or street hip and inviting isn’t an ancillary checklist but a real-life experience celebrating the neighborhood and its culture. This culture thrives when there is a well-balanced retail mix of known retailers and local businesses, combined with unexpected creative placemaking initiatives like green spaces and art installations.

We’d love to hear about your experiences shopping along these amazing streets. Please share your pics and stories with our team on social using #CoolStreetsShopping: LinkedIn: Anjee Solanki; Instagram: @retailinrealtime . Let’s celebrate the vibrant cultures and communities that make these streets so special!