During the peak Boho period in the noughties, the Olsen twins, Mary-Kate and Ashley were seen slinging toddler-size bags over their shoulders while still maintaining a ridiculously chic look. These hobo bags were all the rage among the party girls featured in the pages of Vogue in the early 2000s. It was the iconic carryall – placed in the same league as Dior’s original Saddle bag — before the arrival of micro purses, mini bucket bags and belt bags.

A hobo bag is made to carry just about anything. Its strap is strong and sturdy while its body is expandable, curvy and sometimes with a bit of slouch. It is flexible to fit pretty much everything from your denim jacket to a large water bottle and books.

Kate Spade New York pre-fall 2019 looks include some hobo numbers with the earthy slouchy shaped bag on the left and a duotone contemporary rendition for the millennials on the right. (Courtesy of Kate Spade New York)

The recent Kate Spade pre-fall 2019 collection witnessed a beautiful rendition of the hobo bag with a rounded design in earthy suede. We’ve also witnessed several outstanding hobo bags from the spring/summer 2019 runways including the supersized Bow Bag by Loewe and a leather iteration shaped like a boxer’s maize ball at Paco Rabanne – suggesting a comeback since its ‘disappearance’ circa 2005. The recent hobo bags are more structured, pared back with a sleeker look as compared to its raggedy origins.

If you want that freedom to lug and haul all your belongings wherever you want to go while still looking stunningly fashionable, you can always rely on the hobo bag – it will never let you down. Here are our top picks fresh from the latest spring/summer collections.

(Featured images courtesy of Loewe)