Every city reigns supreme in the eyes of its very own, and how could it not?

No one understands the rhythm and roots of a place better than those breathing life into it each and every day. Whether it’s through their sacred creative crafts that shape the culture of their city, or a commitment to fostering community there that ultimately transcends from IRL to URL, they catapult their local scene to the global stage—and we soak it all in. Their treasured hidden gems, neighborhood hotspots, and cultural hubs become the bucket list wonders we aim to cross off—and this summer we did just that with Carrera and company.

It’s not often that a brand hits the 70-year mark, but the house of heritage eyewear has set the standard for sports-derived shades over the past seven decades, and in the season of sun-kissed streets and lazy, long days, Carrera commemorates the milestone moment with a seven-city tour de force spanning two countries. The anniversary affair—or better yet, affairs —came to life from coast to coast of the U.S. and its northern neighbor, Canada, as part of the Italian design icon’s “Paint My Ride” competition.

Carrera set up shop in Miami, Houston, Chicago, Vancouver, San Diego, Philadelphia, and finally, Toronto for their retro ride showdown. Featuring top visual artists from each city, they competed for a spot in Carrera’s storied history with their one-of-one works of art on vintage wheels. We got a front-row seat to the action, but on the passenger’s side, as local tastemakers took the wheel and gave us a tour of their city’s sights and sounds.

Keep scrolling below to see how we spent a day with them and Carrera in their city.

Drewincolor  – Miami

Neither we nor Carrera could miss out on that Miami weather, and Drew made sure that we got a real taste of the 305. A creative chameleon, Drew’s authentic approach to style is highlighted in her content creation and bold aesthetic as a stylist, clothing and graphic designer. While Miami weather is temperamental, she doesn’t let it dictate her wardrobe, nor the trend of over-the-top dressing, preferring to stay true to her personal tastes inspired by the city’s iconic Art Deco architecture and colorful landscape. The Carrera shades she chose to complement her look reflect her personality perfectly, capturing her strong sense of confidence while adding a fun flair.

Jorge “Jorgey” Casanova – Houston

In H-Town, we linked up with local legend Jorge “Jorgey” Casanova to show us how things go down in the south. The brains behind the streetwear brand DIOS (Dit It Ourselves) styled his earth-toned, self-designed silhouettes with classic Carrera frames, ahead of his pit stop at Houston’s “Paint My Ride” pop-up. Casanova chopped it up with the two competing artists, Floyd Mendoza and Zuzu, breaking down their colorful, custom paint jobs on the vintage cars.

SOLOCELO - Chicago

We had to head to the Windy City to catch all the vibes with born-and-bred native, SOLOCELO. At 26 years old, Chi-Town’s very own has already solidified himself in the city’s creative scene as a rising musician, actor, and sartorialist. The “MOST DAYS” rapper has an affinity for oversized silhouettes in washed shades, often pairing them with high-quality accessories—in this case, the Italian brand’s sleek sunglasses —to bring his look full circle. SOLOCELO showed us the best sides of Chicago—though there are no bad ones —spotlighting how the city’s culture keeps him connected to his creativity.

Nina Huynh - Vancouver

Home is where the heart is, and for Nina Huynh, that’s Vancouver—or any space she can curate into a cozy, inviting place as a home influencer. An actress and digital style savant as well, Huynh held her Canadian city down when we spent the day together, walking us through the ways British Columbia has taught her to embrace alignment and appreciate a slower, steadier pace of life. Although she’s originally from San Francisco, she’s adjusted to the Vancouver lifestyle, just as her style has evolved with it. But, for Huynh her philosophy is simple, as long as she looks good she feels good.

Uwila “Uno” Simposya - San Diego

Where corporate and creative worlds meet is where San Diego-based creator Uwila “Uno” Simposya comes alive. During the day, the Zambian trendsetter is dedicated to the hustle and bustle of 9-to-5s, but after hours, he pours his all into his online fashion and lifestyle content where he weaves his love of self-expressive style and storytelling all in one. Having spent years hopping from different cities—from his hometown in Zambia to Seattle and now SD—Simposya has learned that every place he’s called home adds a new layer to his style and story.

Kwame Kadahndi - Philadelphia

“There’s no place like Philly.” Those are the wise words of native Kwame Kadahndi, who’s never played about the city of Brotherly Love and certainly does not play about his personal style. According to him, the vibes in Philadelphia are “A1,” and fuel his confidence to curate his retro-rooted aesthetic—these days inspired by Lenny Kravitz and the 1960s/70s Black Panthers—but with a streetwear twist. Philly’s the place that built him, brick by brick, and he has the city’s imperfections that are truly part of its charm to thank.

Ola “ihatemyfits” Oladmeji - Toronto

He’s a Naija boy, but he calls the 6 home. His online handle may be “ihatemyfits,” but Ola has a loyal following that loves them. The 23-year-old credits his mother’s intentional style sensibilities for his minimalistic looks where he manages to keep things simple while still making a statement. With his classy but never flashy ‘fits, he’s able to stand out amongst Toronto’s eclectic style scene while making his mark in the space, just like the city’s hustle culture taught him, and he showed us on the final stop of our “On the Road” social series.

Click here to discover more from Carrera's seven-city tour de force.