Fedora Hats and Four Other Essential Styles for Your Fall Wardrobe

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Ahh the hat, an accessory men should not (or cannot, depending on the climate where he lives) leave home without this Fall.  Hats come in all shapes and shades, but there are five key styles fashionable gents should make sure to have on hand as the weather begins to change.  Read what they are and how these headpieces evolved.

The Fedora

“Messenger” Fedora from Tenth Street Hats, $100

First worn in the late 1800s by women, the fedora became popular with men in the 1920s after the then Prince of Wales was seen wearing it regularly.  This hat has gone in and out of style over the last century but has recently seen a resurgence in popularity.  It is also very versatile, easily worn with a suit as well as a more casual look like jeans and a button-down shirt.  A tip is to buy a fedora in a dark, neutral color you can easily mix with your Fall pieces.

The Beanie

Balenciaga Beanie from Mr. Porter, $270

This is the ultimate cool guy hat.  First popularized in the early 1900s, the beanie was immediately adopted by students and blue collar workers alike, the latter using it to keep warm while working outside during the colder months.  The beanie experienced an uptick in popularity in the 1990s when minimalism, grunge and hip-hop inspired looks were in fashion. This hat continues to be a fall go-to and is definitely one you can easily incorporate into any street style look.

The Flat Cap

Cashmere Gill Cap from Lock & Co. Hatters, $263

Now often associated with older men, the flat cap rose in popularity as a standard accessory for young boys in the early 20th century.  It gained its nickname, “the newsie,” because of its association with boys that delivered newspapers at that time. Having gained a more mature audience since then, the flat cap has become a common wardrobe staple in menswear.  Pairing it with a statement coat is always a good look for fall.

The Baseball Cap

Yankees Baseball Cap from Lids, $39.99

Probably the most commonly worn headpiece on the list, the first baseball caps were made of straw and worn by players of the New York Knickerbockers in the mid-1800s.  Evolving from straw, baseball caps now appear in all colors and continue to be affiliated with sports teams, as well as luxury fashion houses and everything in between.  While it is easy to style down this type of hat, take your fall look to the next level by pairing it with something a little more unexpected like a casual suit or blazer.

The Bucket Hat




North Face x Supreme Bucket Hat from StockX, $65

Originating in the early 1900s as a hat worn by Irish fishermen for protection from the rain, the bucket hat was later used by soldiers in World War II and the Vietnam War.  It gained mass appeal during the height of the “mod” look of the 1960s, and peaked again later in the century thanks to the hip-hop stars of the 1980s and 90s. Although it went out of fashion for a bit, the bucket hat is back and more popular than ever.  Consider purchasing one in a solid color to go with a crisp monochromatic outfit this fall.

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