(Just make sure you find a good shoeshine.) $8,900 Ralph Lauren Boston Alligator Bag Ralph provides a miniature padlock in case you don’t want strangers stealing what’s inside your bag.

Still, the DNA of the Polo Play is clear. There’s an innate ease in the bag’s shape and silhouette that feels uniquely evocative of Ralph Lauren’s signature preppy and not too polished ...

Tapping into the legacy of the Ralph Lauren brand, the design was influenced by equestrian styles and vintage identification bracelets (usually engraved similar to the bag’s clasp). The rich ...