This season, handbags are having a moment—and by “moment”, we mean a full-blown expansion. The new silhouette is unapologetically oversized: capacious, slouchy, and just a little bit bossy. Saint Laurent leads the charge with its trio of heavy hitters—the sculptural Mombasa, the quietly commanding Icare, and the elegantly undone Amalia—each one less “bag” and more portable lifestyle.

Elsewhere, Bottega Veneta’s Barbara tote delivers that signature house tactility in generous proportions, while the Louis Vuitton Neverfull GM remains the gold standard of classic utility—still, frankly, unbeatable. For something softer, TOTEME’S Roam tote and Anine Bing’s suede carryalls offer a more languid take; Valentino and Gucci, meanwhile, keep things polished with structure and gleam.

How to wear? Think contrast. An oversized bag works best against something controlled: sharp tailoring, a neat knit, a dress that knows its lines. Or lean in—add to denim and flats for that studied insouciance. The trick is nonchalance: as if you always carry your entire life with you, and might casually produce a novel, a laptop, and a spare pair of heels at any moment. 

Here is our edit of the best super-sized bags available on the Street now.