Fall and Winter Hats Seasonal Style Guide


Five Timeless Fall & Winter Hat Looks That Everyone Should Own 


1) The Classic Black Fedora


  A good quality black fedora is the “little black dress” of the hat world. It’s timeless, classic, looks good on everyone, and is universally appropriate. Since the turn of the century, this iconic hat has eclipsed most other styles as THE hat to own. Whether you choose a short, stingy brim or one of our more wide-brimmed styles, you are sure to look suave and put together in this hat.


The Kenny K Wool Felt Safari Fedora is a beautiful center-dent style made of quality wool.The 2 ½” brim makes this the perfect fedora for a casual leather jacket or with a suit coat.


Our Dorfman Pacific Crushable Wool Felt Fedora Hat is the perfect stingy brim style to wear with a suit. And it’s not just warm; it’s also comfortable, matchable, and crushable for travel. You can’t go wrong with a quality piece that stands the test of time.



  2) The Watch Cap



 In use since the 1500s, the watch cap’s design is a perfect throwback to the original knit caps invented in Monmouth, Wales. A staple of US soldiers and sailors since World War II, the watch cap’s chunky knit and close fit mean it perfectly protects your head and ears on a cold winter day. Fishermen, adventurers, and even paratroopers would popularize this hat even further, but you don’t have to be an outdoorsman to wear this style. With such a storied history this hat is a perfect way to dress down on a chilly weekend without looking sloppy.


Our Rothco Acrylic Watch Cap is a classic military style beanie that is washable and will last for years. It makes a great transition piece from summer to fall but it’s even better with a thick winter coat against ice and snow. Made in the USA, it’s a little piece of American heritage for your closet.




The No Bad Ideas Zander Beanie is a great way to add texture and street cred back to your basic jeans-and-tee combo this fall. A modern take on a classic and understated style, it features chunky soft acrylic and an inner “stash pocket” to hide a key, emergency money, or gum (so you don’t have to share).



3) The Western Style Hat


Invented by John B. Stetson, the “Boss of the Plains” introduced in 1865 sported a high crown for insulation and a broad brim and light coloring for protection from the sun. This style wouldn’t necessarily be recognized today as a western hat, but would eventually (through modifications by the cowboys that wore them) give way to the style we know and love today. Though you probably don’t need to turn up the sides of your hat to lasso cattle anymore, western style hats (in both styles) are still in vogue. They strike a gallant and timeless silhouette with or without rodeo-ready accessories. 


A Scala Wide Brim Safari Hatis the perfect hat for a wild spirit. The soft felt and adjustable interior band will keep you warm and very comfortable! Pair it with a patterned poncho or skirt for a southwest vibe or a floral dress for a bohemian look.



The Scala Crushable Wool Felt Outback Hat is subtly rugged with its leather band and water repellent materials. It’s crushable as well, so it’s as tough as you will look wearing it. Jump into your trusty pair of jeans and you’ll truly be ready for any fall activity.





4) Bold Colored Hats



From Cleopatra’s purple sails to the red bonnet rouge of the French revolutionaries to today, colors can make a very bold statement. And what makes more of a statement than a classic hat in a new and exciting hue? Try a traditional fedora in an unusual hue or go with a time-honored floppy felt hat. Bring a little pizzazz to the dark days of winter. Deep colors give new life to the typical and boring.


The Conner Alison Floppy Hat is available in a ton of different colors to match any look you can create. It’s also adjustable, comfortable, and looks great on everyone. The feather gives it a double duty as a boho style that pairs great with a poncho or oversized shawl.


Our Jeanne Simmons Wool Felt Floppy Fedora Hat is soft, wearable, and adjustable. The plain leather-like band keeps it simple and understated. Use it to add a pop of color to an otherwise dreary ensemble or match it and stand out from the crowd.



5) Flat Caps & Newsboys



Since the 14th century, the ubiquitous flat cap has been seen on the heads of young men, old men, tradesmen, cabbies, retirees, academics, athletes, and even celebrities. A low-crowned round cap with a stiff brim, it can be made from just about any fabric; but is especially dashing in tweeds or wool. A newsboy cap is a variant of a traditional flat cap which emerged in the late 19th century. Made of several panels sewn together and topped with a button, it has a short front-facing brim a lot like a modern baseball cap. It’s highly possible the sustained popularity of flat caps is due in part to its many variations and ultimate wearability for both work and play. Whether you call them newsboys, newsies, baker boy caps, Gatsby caps, cabbie hats, or something else entirely, they are a great option for when you want to be sporty but well-dressed.


The new Henschel Faux Leather 6 Panel Cap is a slightly modernized take on an old style. The soft imitation leather makes this hat both distinguished and unbelievably comfortable. It’s truly a timeless hat.



The Henschel New Shape Earflap Cap sports a padded interior, subtle plaid print, and a soft viscose-wool blend. It is timeless, understated, warm, and durable. Pull down the earflaps and this hat becomes the most stylish protection from the snow and ice.



The Henschel Wool Blend 8 Panel Newsboy is distinguished to the bone, but soft and wearable. A smooth wool blend with a faux suede bill, this hat goes great with a sweater and jeans but will match just as well with a thick scarf and dark coat during the icy grip of winter.