Men’s Vintage Style Hats, Retro Hats

Men’s vintage style hats in classic shapes such as the wide brim fedora, derby (bowler), straw panama, gambler, homburg, flat cap, or straw boater are still made today. Each decade had their favorite styles with some minor changes in brim width, band color, crown crease, and straw weave. Vintage men’s hats are highly collectible and quite expensive, but you can find the perfect new vintage-style hat online. Learn about each men’s vintage hats by decade: 1920s, 1930s, 1940s, 1950s, 1960s-1970s.

Be sure to take your correct head-size measurement before ordering.

Men’s Vintage Style Hats

$28.50

Yates Litefelt Fedora - BlackM

$56.25

Niver Pork Pie

$65.00

Bamboo Mowbray

$43.00

Joey Braided Fedora

Wonderful Fashion Mens Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat (Large/X-Large Charcoal)

$39.99

Big Boss Homburg - Exclusive

$73.50

Curtis Limited Edition Fedora - RaisinXL

Classic Fedora Hat for Men & Women Wide Brim Panama Hat Vintage Gangster Hat with Black Band and Feather

BOTVELA Mens 8 Panel Wool Blend Newsboy Flat Cap Herringbone Tweed Hat

Wonderful Fashion Mens Linen 8 Panel Applejack Gatsby newsboy IVY Hat

$125.00

Niall Fedora - Fawn S

Caufields Brown Steampunk Hat with Black StrapsOne Size

Original Panama Hat - White Classic Fedora - Black Band - Toquilla Straw - Handwoven in Ecuador by Ecua-Andino

$120.00

Gangster Fedora - BlackS

Bowler straw hat derby straw hat summer bowler hat edwardian straw hat victorian straw hat mens straw hat custom classic straw hat

Black top hat empire top hat Top hat stovepipe top hat black topper hat zylinder hat 19th century top hat

Empire Top Hat Reggie Top Hat Stovepipe Top Hat Lincoln Top Hat Regency Top Hat Victorian mens Top Hat Empire felt hat Tall Top Hat

Black felt top hat man woman top hat race top hat victorian top hat edwardian black top hat topper hat John Bull top hat

Cowboy Top hat Top hat large brim black felt top hat wide brim top hat western felt hat black topper felt hat big Top Hat

$120.00

1920s Bollman Heritage Collection Fedora - NavyL

$120.00

Derby Hat

$22.00

Pioneer Folk Homespun Cap Pioneer Trek 19th Century historic reenactment pageant theater

Jaxon Striped Band Skimmer

Fanny Pack hat | 80s/90s Nylon Cap for Men & Women | Zipper Pocket & Adjustable

Shelby Peaky Blinders Hat Bakerboy Paperboy Newsboy Cap Retro Vintage Harris Tweed Cashmere Moleskin Bespoke Large Any Size XL Custom Made

Mens Homburg Hat

$125.00

Niall Fedora - Black XL

SEWING PATTERN - Finch 1920s Irish Flat Cap Ivy Cap for Child or Adult patch cap optional ear flap - PDF Download

$200.54

Bowler Hat | The COKE | Black Fur Felt Bowler Hat For Men | Mens Formal Hats

Brown straw Top Hat straw low Top Hat brown Top Hat short crown straw Top Hat summer Top Hat edwardian straw hat straw Top Hat

Men’s Vintage Style Hats at VintageDancer