How a Simple Yet Incredibly Chic Loafer Style Built This Brand

Welcome to Second Life, a podcast spotlighting successful people who've made major career changes—and fearlessly mastered the pivot. Hosted by Hillary Kerr, co-founder and chief content officer at Who What Wear, each episode gives you a direct line to people who are game changers in their fields. Subscribe to Second Life on Apple Podcasts, Spotify, or anywhere you get your podcasts to stay tuned.

There’s nothing quite like a good pair of loafers, and right now, there is one woman completely dominating the loafer game: Jamie Haller with her namesake brand. Specifically, the Jamie Haller penny loafer (which we recently styled for the ultimate holiday look). These shoes are sleek, slightly oversize, and rendered in buttery leather or unexpected suede. They’ve become the “if you know, you know” shoes among editors, stylists, and creators. Yet Haller’s path to becoming a minimalist footwear—and now apparel—darling was anything but linear.

In the early 2000s, Haller cut her teeth in mall retail, working for Wet Seal, Guess, and bebe—brands synonymous with low-rise jeans, rhinestones, and the peak Y2K aesthetic. The jobs taught her the mechanics of trend forecasting and mass production, but they also left her craving creative autonomy. Eventually, she broke away to consult for smaller labels, where she had more intimate interactions with the brands.

Then 2020 arrived. Like many, Haller found herself with time, restlessness, and a sudden urge to build something entirely her own. With zero formal training, she dove into two seemingly unrelated disciplines: home renovation and footwear. Both ventures took off almost immediately. And what began as a pandemic side project quickly evolved into a full-fledged brand.

The shoes really took off, as they were comfortable yet directional, classic yet quietly subversive—exactly the kind of thing that looks better the more they are worn. By 2023, the waiting list for certain styles stretched into the thousands. Last year, Haller continued to expand the brand by introducing apparel like perfectly oversize blazers, slouchy trousers, cashmere sweaters, and tissue-thin tees that feel like true, elevated basics.

Impressively, this year, Haller opened her first brick-and-mortar store in Montecito, California. The 1200-square-foot space—naturally, she designed every inch herself—feels like stepping into a very stylish friend’s home. Limestone floors, custom plaster walls, vintage furniture, and abundant natural light create a serene backdrop for the loafers lined up on oak shelves and the clothing hanging from minimalist rails.

Listen to the latest episode of Second Life to hear how Haller was able to transition from corporate retail to curating something special of her own. And keep scrolling to shop some of our favorite Jamie Haller pieces.

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