If the past few years have proven anything, it’s that hats are making a comeback—and with a vengeance. Nowadays, you can wear them with anything—from a plain white t-shirt to a form-fitting suit. So read on, and learn how best to top your outfits off without just throwing on your old faded ball-cap. And if you’re looking to upgrade even more than your look, don’t miss these amazing life lessons from the likes of Dwayne Johnson, Anderson Cooper, Laird Hamilton, Tom Brady, Mark Cuban, and more iconic men.
$30; buy now at amazon.com
Lightweight mesh hats are great for balmy weather. Pair this Dockers number with our selection of summer menswear style essentials and you’ll be ready to tackle to dog days of summer all season long.
$27; buy now at amazon.com
Before the armies of Reddit claimed the fedora as their standard issue uniform, it was, believe it or not, a classic menswear essential. Well, it’s cool again, as evidenced by this waterproof, army-inspired piece. Of course, if you’re going out in the rain, be sure to waterproof your entire outfit by checking out the essential rain gear every man needs in his closet.
From $66; buy now at amazon.com
There’s more to this Rat Pack–inspired straw hat than meets the eye: It features an elasticized sweat band for maximum comfort and fit.
From $19; buy now at amazon.com
Elegant in its simplicity, effective in its cleanness, this is a hat that would pair beautifully with a subtle, tonal suit. So while you’re at it, check out the 20 sleekest, sharpest suits you can buy while sitting at your desk.
From $11; buy now at amazon.com
For an instant style upgrade to the baseball cap, try out a newsboy cap. They’re classy and stylish, yes, but most importantly, it’s an easy look to pull off.
From $7; buy now at amazon.com
If you’re heading out on a safari—one of the secret escapes trending among the one percent right now, in fact—this khaki piece of perfection is the hat for you.
$42; buy now at amazon.com
No roundup of hats would be complete without at least one baseball cap. As far as baseball caps go, keep things sleek and neutral—this logo-free, solid navy option from Herschel is a prime example of what to aim for.
$50; buy now at amazon.com
As I mentioned, mesh is the go-to for summer. Here’s an option in a darker brown—subtle yet distinctive, and incomparably suave.
From $26; buy now at amazon.com
Consider this familiar khaki piece your backup on that safari.
$30; buy now at amazon.com
Patterns are all the rage. (Just take a look at the Hawaiian shirt trend for proof.) This textured, graphic option is perfect for stepping up your patterns game. Plus, it’s light as a feather—a feature anyone can tip their hat to.
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