A pair of iconic Stan Smiths forgo adidas’ signature stripes in lieu of perforation for a low-key but versatile shoe. The synthetic and leather upper and rubber cup sole are sleek yet easy to care for, while an orthopedic sock liner keeps you on your feet all day. "Instantly comfortable," one Amazon shopper wrote.

"Great fit and comfort when I wore them with socks, no shows, or barefoot. Well made and not showing any wear after a lot of miles. Easy to wipe clean and keep looking white and new."

• Available colors: 2
• Available sizes: 3.5 – 21

One step up from a sneaker but less fastidious than a loafer, the old-fashioned boat shoe only gets better with age. With breathable mesh panels, this Sperry pair won’t look like your grandpa’s loafers, but their leather construction ensures they'll last just as long. They’re treated to be stain- and water-resistant — with rust-resistant eyelets, no less — so they’ll survive whatever you throw at them. Inside is a layer of EVA foam with extra cushioning beneath the heel and a padded tongue so you can go sock-less if you want.

"These shoes fit quite well, are very comfortable and good looking," one fan wrote. "They go equally well with chinos or other casual pants as well as with jeans. They're well made and have met all my expectations."

• Available colors: 19
• Available sizes: 7 – 15 (regular, wide, and extra-wide)

As easygoing as a pair of Toms but a little more versatile, this canvas slip-on sneaker from Lugz is clean and minimalist with a padded ankle and a nice faux-leather heel cap. Two elastic gores make them easy to slip on and off, while a cushioned insole and breathable lining help keep your feet dry and comfortable.

"Better than the version by Vans and about half the price. Shoe quality is exceptional," one shopper wrote, adding, "Very versatile shoe that looks great with shorts and jeans or just about anything really. My go to shoe of the moment."

• Available colors: 20
• Available sizes: 3.5 – 15

Is it a sneaker? A slip-on? A loafer? All of the above, really. These best-selling casual knit shoes are ultra lightweight, clocking in at under 8 ounces each, and so flexible you can fold them in half. The breathable mesh is lined with soft Oxford cloth and there's a nice heel cup for extra durability where it counts. These loafers feature a removable memory foam insole you can easily swap out for your own, laces that can be reconfigured a few different ways, and soles with lug tread for serious traction wherever you go. With 15,000 ratings — the vast majority of them being a perfect five stars — they have earned somewhat of a cult following on Amazon.

"Incredibly light and amazingly comfortable... adjusted the bungee cord laces a bit and have been wearing them all weekend with no slippage," one reviewer wrote. "Great style, great fit and excellent comfortability. Definitely won't be my last pair!"

• Available colors: 32
• Available sizes: 7 – 15

The handwoven panels on these luxury sneakers look sharp as hell without ruining the laidback vibe. Designed in New York and hand-crafted in Brazil, they're made from rich Napa leather and textured suede. The interior is fully padded and lined, with a removable cushioned insole if you prefer your own or need more wiggle room. And that classic rubber tennis shoe sole makes them just as practical as they are good-looking. "This is the best deal I've ever gotten on shoes," one reviewer noted. "These are top quality in material and build. These are $150 to $200 shoes." Pick up a can of leather and suede protectant to keep them looking good as new with zero work.

• Available colors: 13
• Available sizes: 7 – 13

This Clarks chukka boot is built for the outdoors but nice enough for a casual date. And, since they’re Clarks, you know they’ll be reliably comfortable. Available in either a leather or suede upper, they all come with a sturdy rubber outsole for long-term durability. "Been wearing them daily for a year and a half and they have held up very well, and are extremely comfortable," one reviewer wrote. "I don't use them as dress shoes, like some folks seem to. I walk my dog, ride my motorcycles, I've even run and hiked in them before." Just note that some fans recommended sizing down either by a half or full size.

• Available colors: 33
• Available sizes: 7 – 15 (regular and wide)

These Cole Haan wingtips look completely dapper but they have a cushy sneaker sole with the comfort to match. As such, they're actually incredibly versatile. The old-school leather upper is built over a multi-layered insole with plenty of cushioning to provide all-day shock absorption, and a soft fabric lining for a smooth fit and feel. The lightweight sole features rubber panels so you can wear them out no matter what the weather's doing. "As someone who typically wears Converse Chuck Taylors, these Cole Haan Oxfords are a huge improvement," one reviewer commented. "Go very well with jeans and can be worn for miles in comfort."

• Available colors: 5
• Available sizes: 7 – 13

A driving shoe works just as well with a blazer or a pullover. With this one, you can choose from suede or full-grain leather — both have rubber reinforcements on the heel for long drives. A braided leather cable across the instep has the flair of designer pairs, and inside is a padded and contoured footbed. "Totally worth the money. I use them around the house and to run errands," one fan wrote. Another reviewer noted that they lived up to their intended purpose, too, making it easier to drive a stick shift with the extra grip on the heel.

• Available colors: 7
• Available sizes: 6.5 – 15