The first thing to consider when buying a cooler is how you're going to use it. If you aren't heading out for days at a time, you probably don't need an expensive high-end cooler. All the coolers we've recommend above are capable of holding things at a safe temperature for a day, provided you keep them in the shade. Similarly, if you're navigating rugged terrain, you might want beefy wheels—and if you're just going to the beach, you might not need them.
Hard-sided coolers: These range from the old green Coleman coolers—once a staple of every camping trip—to Yetis, which cost as much as cars did when Coleman started making coolers. You might wonder why the Yetis are so expensive. That I can't answer, but Yeti did upend the cooler industry by introducing rotational molding, or “rotomolding,” where melted plastic is molded over foam insulation in one piece. Rotomolded coolers offer seamless, uniform density in their walls and lids, which drastically improves a cooler's performance. In contrast, those ancient, affordable plastic coolers we've all used have thinner walls, leaky seams, and less insulated lids. Whether you need the extra insulation depends on what you're doing and how hot it is when you're doing it. Want to learn more? Our In-House Know-It-All has a more thorough insulation explanation.
Hard-sided coolers generally have the luxury features you want, like leakproof lids and drain plugs, and some are even bear-resistant (check this list of bear-proof products if you're headed into ursine country). The downside is that these coolers are generally huge and heavy.
Soft-sided coolers: Soft-sided coolers include everything from well-padded, impressively insulated sling bags (like the Yeti Hopper Flip above) to roll-down, dry-bag-style coolers perfect for those mild beach days. The best soft coolers are easier to carry, pack away easily when not in use, and have a versatility that traditional hard coolers lack. (I have used dry-bag-style coolers as, well, dry bags.) Ice doesn't last as long, but for short outings where you don't need a large cooler, these are what we recommend. Our older pick was discontinued; we're on the hunt for another.
Electric coolers: Sure, they're not necessary, but if you're headed out on longer adventures and have access to power, you'll never have to worry about your ice melting.
Other Features to Look For: