Holiday Gift Guide for Stetson Hats- 12 Most Popular Stetson Hats

  • , by Elizabeth Carroll
  • 10 min reading time
Stetson Hats- Holiday Gift Guide

A century ago, the fedora hat was unquestionably de rigueur.

Any man who held a certain station in life (or wanted to) wore a hat as a symbol of status and refinement. The Stetson brand dates back to the late 1800s and their iconic derby and fedora lines almost as far.

From Al Capone and Humphrey Bogart to Winston Churchill and Frank Sinatra, the fedora has held a place fashion and imagery of the first half of the 20th century.

After fading from popularity in the nineteen-seventies, these dapper headpieces resurged to popularity in the nineteen-eighties and nineties. The return of the fedora to global popularity was helped, in no small part, by iconic celebrities like Michael Jackson, and action heroes like Indiana Jones and Rocky Balboa.

Not Just for Men Anymore

That renewed popularity continues today, as more and more men and women are donning the classic fedora to express their sense of laid-back rakish style.

Here are a few of our favorite and most popular styles here at Fashionable Hats, hats that are sure to a big hit this holiday season with your more dapper-minded loved ones.

#1 The Stratoliner 

Any Hat connoisseur will recognize the iconic Stratoliner by Stetson.

Named for Boeing’s groundbreaking 307 Stratoliner aircraft from the 1940s, this fedora, which launched the same year, was likewise a symbol of pride and luxury.

The Stratoliner features a 2.5” brim, teardrop crown, and trademark Boeing 307 hatpin, paying homage to its namesake. Satin-lined and crafted from the highest-quality fur felt material and a leather sweatband for an exceptionally comfortable fit and classic look.

With a popularity that’s endured through the decades, this hat is a timeless look that’s as sleek and modern now as it was when the 307 first took to the air.

Perfect for the jet-setter on your Christmas list!

Stratoliner - Stetson Fur Felt Fedora Hat - TFSTROBStratoliner - Stetson Fur Felt Fedora Hat - TFSTROB


#2- Frederick Wool Felt Fedora Hat

This 100% water-repellent Fredrick wool felt fedora adds just the right touch of class, whether suited up for a night on the town or kicking back in your favorite pair of jeans.

Sporting a 2” underwelt rolled brim, a 4 1/2" center dent crown, thick grosgrain band, and the iconic Stetson hat pin.  Satin-lined, with a leather sweatband to ensure comfort, the Fredrick is loaded with features typically found only in hats at a much higher price point.

If you’re looking for style, affordability, and comfort in a great winter-weather hat, look no further than the Fredrick Wood Fedora.

Stetson Frederick Wool Felt Fedora Hat - TWFRDK

#3 - Cromwell - Stetson Crushable Wool Fedora Hat

One of Stetson’s most popular everyday hats, the Cromwell crushable wool fedora boasts a hip, casual, outdoorsy style with its simple leather band for the casual man.  This hat is crushable for easy packing, without losing its original shape, and water-repellent for those drizzly winter days.

The Cromwell features a center dent crown, dri-lex sweatband, and elegant leather headband.

Practical with a hint of debonair, this lightweight, comfortable hat is the choice for the well-groomed outdoorsy folks on your list!

Cromwell - Stetson Crushable Wool Fedora Hat - TWCMWL

#4 Temple - Stetson Fur Felt Fedora Hat

The Temple Stetson Fur Felt Fedora is a long-time crowd pleaser and a salute to the toe-tappin’ finger-snappin’ East Coast jazz bars of the 1940s. A center pinch 4 1/2” front crown,  a 2 5/8” brim, and a wide grosgrain ribbon hatband create a timeless elegance and iconic look.

The Temple is lined with satin and features a genuine roan leather sweatband for added comfort. The band is offset by a bold feather accent.

Available in seven colors, this fedora is sure to be a holiday hit!

 Temple - Stetson Fur Felt Fedora Hat - TFTMPL

#5 Chatham - Stetson Fur Felt Fedora Hat

The Chatham fur felt fedora, with its 4” teardrop crown and 2.25” brim lends a look of dignified confidence to any wearer. The quintessential fedora from Hollywood’s golden age, the Chatham was the hat of choice in nearly every movie released in the 1930s and ‘40s.

The high-quality fur felt blend makes the Chatham incredibly soft to the touch, while the genuine leather sweatband ensures an extra comfortable fit.

Make someone’s holidays with this Oscar-winning look!

Available in 5 beautiful colors. Also available in wool.

Chatham - Stetson Fur Felt Fedora Hat - TFCHAT

#6 Belfast - Stetson Fur Felt Fedora Hat

Timeless and stylish, the Belfast, with its two-tone band, is the definition of classic cool.

Featuring a 4 1/2" teardrop crown and a 2 1/8" brim, a beautiful matching fur blended hatband, and a flexible leather sweatband to keep you comfortable even in the hottest weather.

A traditional look that’s as cool today as it’s ever been.

Simple yet classy.

 Belfast - Stetson Fur Felt Fedora Hat - TWBLFS

Not sure what size hat is right for someone on your gift list? Order a gift certificate and we’ll include this free hat sizer and gift box!

#7 Stetson Cruiser Crushable Wool Felt Fedora

Got a lover of the outdoors on your list? The crushable Stetson Cruiser is the perfect gift for the avid hunter, hiker, or angler who likes a little style along with the convenience of a packable hat that won’t lose its original shape.

Built for warmth in the winter, and shade in the summer, this fedora has been a pinnacle of fashion dating back to the roaring 20s.

Whether they’re sitting around the campfire, cutting a rug, or enjoying a Sunday drive, this high-quality wool felt fedora will cap their adventures for many years to come.

Stetson Cruiser Crushable Wool Felt Fedora Hat - TWCRUR

#8 Bozeman - Stetson Crushable Wool Felt

Another classy (and crushable) option, the Stetson Bozeman wool felt hat, with its 3” brim and 4.5” crown, is also a great, water-repellent, choice for the outdoor adventurer who enjoys a little more cowboy in their look.

Built to make it to the end of the trail, day in and day out, the Bozeman features a teardrop pinch crown, classic 3.25" brim, and a Dri-Lex cloth sweatband for added comfort. It also sports a rich leather hatband with a lasso tied accent.

A hat as authentic and adaptable as the American spirit!

Bozeman - Stetson Crushable Wool Felt Outdoor Hat - TWBOZE

#9 Jet 707 - Dobbs Fur Felt Fedora Hat

Made with ultra-soft rabbit fur, the Dobbs Jet 707 Felt Fedora is all about comfort and class.

With a center dent pinch crown and a shorter (1 7/8”), or “stingy” brim the Dobbs is a handsome and hip looking hat and one fashion accessory that anyone would love to find under the tree!

Exceptionally comfortable yet stylish, the black bowtie band, feather, and Stetson pin add a touch of refinement.

The Jet 707 is part of Dobbs' Golden Coach collection – and is made from the highest quality of felt offered by Dobbs.

 Jet 707 - Dobbs Fur Felt Fedora Hat - DFJET7

#10 Black Hawk - Stetson Felt Gambler Hat

When it comes to a cool cowboy look…the Black Hawk Felt Gambler Hat is tough to beat.

Popular with both women and men, and a favorite of musicians around the world, the Black Hawk struts its stuff with a wide (3.5”), flat brim and silver studded concho accented leather hatband.

The crown is teardrop style and features a padded fabric Dri-Lex sweatband for superior comfort.

As if all that weren’t enough, The Black Hawk is also water-resistant and crushable!

Black Hawk - Stetson Felt Gambler Hat - SWBKHK

#11 Whippet - Stetson Wool Felt Fedora Hat

As sleek and stylish as the racing dogs it’s named after, the Whippet wool felt fedora is a featured style in Stetson’s 150th Anniversary Collection.

Made from Royal DeLuxe quality fur felt, the brim size is 2.5” with a 4” teardrop, pinch-front crown, and grosgrain hatband along with satin lining and a cowhide sweatband for luxurious comfort. 

This is the fedora for someone who loves a vintage look that never goes out of style!

Whippet - Stetson Caribou Fur Felt Fedora Hat

#12 Rockway - Stetson Fur Blend Felt Fedora Hat 

A favorite amongst the hipster crowd, The Rockway is a 3 1/8" wide-brimmed felt fedora with bound edge and a distinct 4” diamond pinch front gambler crown, that really makes it stand out among fedoras.

Part of Stetson’s Medalist Collection, this fedora features an interior cowhide sweatband for added comfort, and a ribbon hatband adorned with a box, a Stetson hat pin, and 2 feathers.

If there’s someone on your holiday shopping list who likes their look to be just a little different from the crowd, they’ll love the Rockway.

 Rockway - Stetson Fur Blend Felt Fedora Hat


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