Milano sandals, $120
Allow us to walk a slight sartorial tight rope for a moment. To the gents who turn their noses up at the thought of sandals: There's more to life than just boat shoes. When you're at the beach (or your gym's locker room), a pair of simple rubber Havaianas are a good thing to have underfoot. But this spring, there's a slew of simple sandals (dubbed Jesus sandals by the #menswear crowd) on the market. And a sturdy, unadorned leather pair can work rather nicely on the right guy. Just make sure the setting is as casual as the clothes—in this case, trim shorts, relaxed chinos or a linen suit—and they'll easily take you from the beach to the bar without shame.
The "Birks" are Back
For years, Birkenstock sandals were considered the dorky, hippy-dippy footwear of choice for slackers and baristas. But these days, thanks to some cool collaborations and the eventual swing of the style pendulum, you're likely to find them on the feet of stylish guys everywhere.
If you're still on the fence about grown-up sandals, opt for some leather flip-flops. They strike a good compromise between the comfortable footwear you've worn before and the slicker, more grown-up styles of today.
The "Dressy" Option
These are the leather styles that you likely noticed during the fashion week collections and in all the ads these days. They're the sandals being talked about when the term "mandals" gets thrown about. And as much as we despise that term, we're warming up to some of these styles.
These simple leather sandals are made in Jerusalem from top quality leather by Camel Shoemaker, a brand that's been handcrafting footwear since 1837. What's more, the soft synthetic sole makes them easy to walk in too.