Top 10 Men’s Straw Fedora Hats

Straw hats and the fedora style in many ways contradict each other. Straw hats are associated with casual, laid-back vacationers or farm hands basking in the Panama sun. Fedora hats on the other hand bring up imagery of immaculately-dressed dandies, film noir movies, gangsters, Indiana Jones and the Prohibition-era.

So why is the world did fashion experts decide to breed the straw hat with the fedora? The answer lies in those grey areas of fashion sense, when function trumps form. A man sitting outside in the sweltering hot sun during a formal occasion would be doing himself a big favour by wearing a straw fedora. Straw can be dyed in various colors to match his suit (although natural can work just fine), the hat shape is a good fit fashion-wise, and since straw is great at blocking the sun’s harmful rays, he can stay comfortable outdoors for hours.

The suns heat can be exhausting; coming prepared with the right hat can sometimes make the difference between having a great time and feeling too beat down by the weather to “dig in” socially.

Other than that a straw fedora keeps you cool, while avoiding the straw cowboy hat cliché. If you gravitate towards urban living, the “city slicker” at a rodeo look probably won’t work for you. Arguably, a straw fedora is appropriate for a greater variety of occasions.

The following hat recommendations are based upon my personal tastes. There is a multitude of choices out there and even customized options for the savviest customers. If you’re not sure where to start, this list is perfect. Only well-made hats backed by a good reputation (or value for the dollar) were considered. Prices range from around $50 to $200. If a hat by a given manufacturer looks well-made but isn’t quite “you”, be sure to dig a little deeper within that brand’s inventory.

Basino - Shantung Dress Hat
Dobbs, $104

This model does an outstanding job of balancing the need to protect your face from the sun and looking great with a suit. The light natural tone looks great outdoors.

Corinth Porkpie - Bari Straw Fedora Hat
Stetson, $93

Stetson has managed to mix formal patterning with a casual shape. Create types should appreciate the balance of originality and good taste.

Balibuntal Fedora - Straw Fedora Hat
Christy’s & Company Ltd., $164

I can picture John D. Rockefeller wearing this hat while playing croquet with friends and family. This is an iconic, classic design that will never fall out of fashion.

Pebble Beach - Genuine Panama Fedora Hat
Pantropic, $70

If you are strictly concerned about keeping out the sun, this UPF50+ hat is an excellent choice. It’s unique in that it has that panama straw hat look and is shaped like a fedora.

Ryden - Straw Fedora Hat
Bailey of Hollywood Hats, $50

This is an excellent way to keep the fact you are wearing a straw hat on the down-low. The look is about as formal as you can get with a straw hat, mainly due to the sharp band and dark dye.

Madison - Vented Milan Fedora Hat
Dobbs, $98

The Madison has a charming personality, with an eye-appealing loose weave and grosgrain ribbon. It is made with Florentine Milan straw, thus the name.

Monticello - Premier Straw Fedora Hat
Stetson, $198

Stetson excels at making hats that look good with a suit and the Monticello is no exception. The generous 2 ½” does a good job of keeping the sunlight under control.

Habana - Genuine Panama Fedora Hat
Pantropic, $54

This hat by Pantropic has a nice Panama feel to it, with the characteristic dark band. The small but ample 2” brim should do the job on more mild days.

Billy - Straw Fedora Hat
Bailey of Hollywood Hats, $49

Billy won’t do much to block the sun; it’s purely a fashion hat. Everything looks great about this hat from the band to the minimalist texture.

Barnett- Twisted Toyo Straw Fedora Hat
Bailey of Hollywood Hats, $49

Another minimalist hat by Bailey, the Barnett has a very pleasing approach with its use of rich natural tones. The fabric band and small leather loop unifies the look.