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A good crossbody should do exactly as advertised: fit comfortably across the torso and sit at the hip, which means the shoulder strap should measure roughly between 18-22 inches, depending on your height. But beyond that? The possibilities are endless. Consider what you need a crossbody for: a fashion statement? Travel? Hiking around snacks and a water bottle, or just a single tube of lipstick?

Finally, determine the resale value. If you plan on using your crossbody for decades to come, it won’t matter much if the bag is popular on secondhand sellers. But if you’re looking to make an investment, consider which bags are most sought-after. Says Charles Gorra, CEO & Founder of the popular luxury handbag reseller Rebag, “crossbody bags from Hermès, Louis Vuitton, Gucci, and Prada consistently have great resale value,” but Telfar and Jacquemus are also on the rise. We highlight a few of our favorites ahead.

Bottomless tote bags and incandescent evening bags all share a deserved spot in your handbag rotation, but nothing eclipses the versatility of a crossbody. Designed to be hands-free and weight-balanced—no shoulder aches or strap slippage here—crossbody bags are the perfect on-to-go accessory, but their functionality need not beget boredom. Some of the loveliest—and most coveted—luxury bags are crossbody designs, and as new designers enter the market, even those bags below the thousand-dollar price point draw trend-seeker envy. (Just ask Beyoncé.)