How a Basic Yet Exceptionally Stylish Loafer Design Established This Brand

      Welcome to Second Life, a podcast that highlights accomplished individuals who have made significant career transitions and confidently embraced change. Hosted by Hillary Kerr, co-founder and chief content officer at Who What Wear, each episode provides insight into those who are pioneers in their industries. Subscribe to Second Life on Apple Podcasts, Spotify, or wherever you listen to podcasts to stay updated.

      There's nothing quite like a great pair of loafers, and currently, one woman is totally dominating the loafer scene: Jamie Haller with her eponymous brand. In particular, the Jamie Haller penny loafer (which we recently styled for the perfect holiday look). These shoes are sleek, slightly oversized, and made from soft leather or unique suede. They have become the “if you know, you know” footwear among editors, stylists, and creatives. However, Haller’s journey to becoming a beloved name in minimalist footwear—and now apparel—was far from straightforward.

      In the early 2000s, Haller started her career in mall retail, working for Wet Seal, Guess, and bebe—brands known for low-rise jeans, rhinestones, and the peak Y2K style. These roles taught her about trend forecasting and mass production but also left her wanting more creative freedom. Eventually, she moved on to consult for smaller brands, where she had more hands-on experiences.

      Then came 2020. Like many others, Haller found herself with time on her hands, a restlessness, and a sudden desire to create something uniquely her own. With no formal training, she immersed herself in two seemingly unrelated fields: home renovation and footwear. Both endeavors took off quickly, and what started as a pandemic side project transformed into a fully realized brand.

      The shoes gained popularity for being comfortable yet stylish, classic yet subtly disruptive—exactly the kind of items that look better the more they are worn. By 2023, certain styles had waiting lists of thousands. Last year, Haller further developed her brand by launching apparel like perfectly oversized blazers, relaxed trousers, cashmere sweaters, and ultra-soft tees that feel like true elevated essentials.

      Remarkably, this year, Haller opened her first physical store in Montecito, California. The 1200-square-foot space—designed entirely by her—radiates the warmth of a fashionable friend’s home. Limestone flooring, custom plaster walls, vintage furnishings, and abundant natural light create a tranquil backdrop for the loafers displayed on oak shelves and the clothing hanging from minimalist racks.

      Tune into the latest episode of Second Life to discover how Haller successfully transitioned from corporate retail to curating something special for herself. Also, keep scrolling to shop some of our favorite pieces from Jamie Haller.

      Jamie Haller

      The Penny Loafer in Ponyhair Black

      Jamie Haller

      The Polo in Black

      Jamie Haller

      The Fan Jean in Borrego Indigo

      Jamie Haller

      The Ring Tote in Oxblood

      Jamie Haller

      The Archive Heel in Snake Mix

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