27 Most Fashionable Cities in the US

3. Oakland, CA 

Insider Monkey Score: 0.92 

Oakland stands third among the most fashionable cities in the US. Oakland’s retail vacancy rate is under 3%, rivaling that of nearby Walnut Creek. Oakland’s fashion scene is characterized by a DIY, self-made ethos, particularly among the LGBTQ+ and BIPOC communities. Local designers like Dexter Simmons and Anisa Taaj are making waves in the industry, showcasing their work at events like New York Fashion Week and in publications like Vogue Italia. Women are at the forefront of Oakland’s fashion scene, with local designers like Lesley Evers and Melissa Kantor gaining recognition for their work.