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

£35.95

Jaxon & James Tyrolean Hat - Green

Different Touch 100% Wool Felt Derby Bowler with Removable Feather Fedora Hats

$73.50

Blixen Limited Edition Fedora - Evening SkyXL

$93.12

Straw top hat straw topper hat Edwardian straw hat mad hatter hat Victorian top hat xl straw top hat man straw top hat cylinder hat

$100.00

1880s Bollman Collection Topper

$92.00

Wind River by Bailey Columbia LiteFelt Outback

Belfry Bowler Derby 100% Pure Wool Theater Quality Hat in Black Brown Grey Navy Pearl Green

Belfry Topper 100% Wool Satin Lined Mens Top Hat in Black Available in 4 Sizes

$125.00

1930s Bollman Heritage Collection Trilby - SenateL

$86.25

Wind River Switchback Outback Hat - PecanXXL

$73.50

Blixen Limited Edition Fedora - CordovanXL

$29.99

Quest Safari Fedora - Exclusive - LodenL

$80.00

Waits Braided Pork Pie - CopperXL

$75.00

Billy Braided Trilby - Deep RedS

$66.00

Wilton Fedora - BlackM

$90.00

Big Zwey Top Hat - Black7 58

$86.25

Wind River Switchback Outback Hat - BlackXS

$120.00

1900s Bollman Collection Homburg - BlackXL

$200.54

Bowler Hat | The DERBY | Brown Fur Felt Derby Hat For Men | Mens Formal Hats

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

$95.72

Black straw boater hat man and woman black straw boater black straw gondolier hat summer black straw canotier summer black straw hat

$160.00

Konrath Litestraw Fedora

$185.00

Walsh Elite Pork Pie

$100.00

1940s Bollman Collection Pork Pie

Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown and Striped Bands

$130.00

Tino LiteFelt Fedora - Rosewood XXL

$130.00

Tino LiteFelt Fedora - BlackXXL

$61.00

Wool 504 - Vino

$80.00

Bamboo Mowbray - Dark BlueS

$49.00

Wilton Fedora - Putty

Men’s Vintage Style Hats at VintageDancer