From the Mombasa to the Paddington: Hobo Bags Are Having a Moment

The early 2000s hobo bag is firmly back in rotation. Once a staple of the era’s street style and celebrity culture, these slouchy, oversized shoulder bags are now reappearing on runways, in vintage edits, and on the arms of a younger generation discovering their appeal for the first time.

The resurgence includes some of the most recognisable designs of the time. The YSL Mombasa, designed by Tom Ford in 2001, stood out immediately for its curved silhouette and distinctive deer horn handle. It was elegant without being delicate, and felt more like a sculptural object than a standard luxury accessory. It was quickly picked up by stylists and editors, becoming a defining piece of Ford’s era at Saint Laurent.

Around the same time, Balenciaga’s City bag, designed by Nicolas Ghesquière, gained traction in a completely different way. Initially considered too soft and casual for the house, it wasn’t even meant for production. But once models started carrying it backstage, demand grew fast. Worn by the likes of Kate Moss and the Olsen twins, it became an essential of off-duty fashion, instantly recognisable for its tassels, faded leather, and relaxed shape.

Other cult favourites followed. The Chloé Paddington, with its oversized padlock and sturdy leather, was one of the first bags to have a genuine waitlist before release. It was heavy, bold, and slightly impractical, but that was part of its charm. The Miu Miu Vitello Lux, by contrast, offered a more understated version of the hobo shape: soft, ruched, and easy to wear, it became a quieter classic. And the Loewe Nappa Aire, with its ultra-soft leather and rounded structure, offered something subtle and tactile that still holds up today.

Their return now makes sense. In recent years, fashion has favoured structure and minimalism, with micro-bags and logo-less leather dominating the luxury market. The hobo bag is a reaction to that, bigger, softer, and less rigid in both form and attitude. These bags are meant to be used. They’re roomy, practical, and designed to age well.

Many of the originals are being reissued or are climbing in value on resale platforms. At the same time, newer brands and designers are borrowing heavily from the early-2000s hobo blueprint, reviving the aesthetic with updated proportions and finishes.

The trend speaks to a shift in mood. There’s a renewed appreciation for pieces that have some weight and history to them, bags that don’t feel purely decorative. The hobo bag, once seen as the ultimate Y2K status symbol, is now being worn for its comfort, practicality, and character. It’s a return that doesn’t feel forced. Just relevant.

Written by Vanessa Twerefou