Chanel 2.55

If the Chanel 2.55 were a person, it'd be that effortlessly cool friend who doesn't even TRY yet somehow nails it every time. In the 'Greatest Handbags of All Time' league, this icon plays dirty—flaunting that quilted leather like it’s nobody's business. Fans? More like cult followers who'll argue its supremacy at any brunch, twice on Sundays. Ever tried convincing a 2.55 devotee there's another contender? Good luck—you'll need it. This bag doesn’t just enter rooms, it owns them. Debate over, folks!