Men’s vintage style hats in classic shapes such as a the wide brim fedora, bowler or derby, panama, gambler, homburg, flat cap, or boater. Each decade had their favorite styles with minor changes in brim width, band color, crown crease and straw weave. Learn about each decade or find your perfect new vintage style hat below: 1920s, 1930s, 1940s, and 1950s
Vintage Style Men’s Hats
Shelby Tweed News Boy Cap
£54.17
BOTVELA Mens 8 Piece Wool Blend Newsboy Flat Cap Herringbone Pattern in Classic 5 Colors
$19.99
Brixton Brood Snap Cap GreyTan Plaid Caps
$39.00
Big Boss Homburg - Exclusive
$39.99
Frederick Fedora
$60.00
Dobell Mens Black Top Hat 100% Wool Formal Wedding Races
£39.99
Big Boss Homburg - Exclusive
$39.99
Big Boss Homburg - Exclusive
$39.99
Men’s Newsboy Gatsby Hat Vintage Beret Flat Ivy Cabbie Driving Hunting Cap for Boyfriend Gift
$29.99
Thurman Panama Fedora
$155.00
Wonderful Fashion Mens Linen 8 Panel Applejack Gatsby newsboy IVY Hat
$11.98
BOTVELA Mens 8 Piece Wool Blend Newsboy Flat Cap Herringbone Pattern in Classic 5 Colors
$19.99
Wonderful Fashion Mens Linen 8 Panel Applejack Gatsby newsboy IVY Hat
$11.99
Epoch Mens Classic 8 Panel Wool Blend newsboy Snap Brim Collection Hat
BOTVELA Mens Premium Wool Classic Flat Ivy Newsboy Cap Herringbone Pattern Flecked Hat
$29.99
Biddy Murphy Irish Tweed Caps 100% Wool Charcoal Herringbone Made in Ireland
$84.99
BRIXTON Mens Brood Newsboy Snap Hat
$37.11
Blixen LiteFelt Fedora
$98.00
Bailey Kenrick - Wool Porkpie Hat
$57.50
Historical Emporium Mens Deluxe Velvet Embroidered Smoking Cap
$49.95
Salem Braided Fedora
$66.00
Ace of Spades Gambler Hat - Exclusive
$39.99
Darron LiteFelt Pork Pie
$95.00
Wind River by Bailey Columbia LiteFelt Outback
$88.00
Britten Newsboy
$36.00
Dobbs Wellington - Linen 84 Cap
$49.98
Salem Braided Fedora
$66.00
Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora in Black Grey Navy Brown Pecan
Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora in Black Grey Navy Brown Pecan
$44.95
Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora in Black Grey Navy Brown Pecan
$44.95
Mens Top Hat Satin Lined Topper by Belfry 100% Wool in Black Grey Navy Pearl
$39.95
Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown and Striped Bands
$39.95
Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown and Striped Bands
$39.95
Caufields Brown Steampunk Hat with Black StrapsOne Size
$24.99
Danger Pork Pie - Exclusive
$39.99
Runkle Straw Pork Pie
$56.00
30s 20s navy blue CAP cotton linen blend swing lindy hop 1930 1920
$113.04
Lord Plaid Ivy Cap
$85.00
Levoy
$60.00
Wool Hawker
$60.00
Larkin LiteStraw Pork Pie
$112.50
Belfry Bowler Derby 100% Pure Wool Theater Quality Hat in Black Brown Grey Navy Pearl Green
$39.95
Robin Litefelt reg Fedora
$105.00
Darron LiteFelt reg Pork Pie
$95.00
Derby Hat
$110.00
Maglor Fedora
$59.00
Historical Emporium Mens British Empire Pith Helmet
$44.95
Lieutenant Cap
$38.00
Stacy Adams Polybraid Pinch Front Fedora with Silk Band Cognac Fedora Hats
$22.50
Mens Scala Classico Wool Felt Fedora - Black
$46.00
Mens Scala Classico Wool Felt Snap Brim Hat - Grey
$51.00
Mens Scala Straw Boater Hat - White
$63.00
Olin Fedora
$350.00
Quest Safari Fedora - Exclusive
$39.99
Argo Wool Fiddler Cap
$25.00
Scala Panama Boater Cherry Hill - Straw Boater Hat
$140.00
SCALA Straw Boater with Two-Tone Stripe Grosgrain Ribbon Bleach Caps
$39.18
Brixton Wesley Fedora HeatherGreen Traditional Hats
$62.00
Trinidad Panama Boater
$108.00
Wool Enfield
$61.00
1880s Bollman Collection Topper
$100.00
Mens Scala Straw Trilby -
$130.00
Indiana Jones Hats Classic Indiana Jonestrade - Wool Fedora Hat
$51.75
Wool Twill Fisherman
$54.00
Fisherman Cap
$35.00
Conner Hats Time Lord - Wool Top Hat
$69.00
Hamilton GentleFelt Fedora
$65.00
Hamilton GentleFelt Fedora
$65.00
Mens Rounded Top 1 Wool 4 Inches High Crown Dark Brown Hat
$59.00
Max Mara Womens Hats Navy Blue Brunico Hat
$129.60
Runkle Straw Pork Pie
$56.00
Frederick Fedora
$60.00
Cowpuncher Western Hat
$120.00
Frederick Fedora
$60.00
Derby Hat
$110.00
Frederick Fedora
$60.00
Frederick Fedora
$60.00
Creel Litestraw reg Fedora
$120.00
Frederick Fedora
$60.00
Cowpuncher Western Hat
$120.00
CHARM Mens Summer Beanie Cotton - Womens Crochet Slouch Cap Hand Made Chemo Hat
$17.00
KUYOU Womens Multifunction Plus Cashmere Hat Skull Cap Scarf
$9.99
Charm Men Summer Beanie Knit - Women Hipster Slouchy Hat Boho Street Fashion Cap
$20.20
Elope John Bull Low Steampunk Top Hat in Brown
$35.25
Sterkowski Maciejówka Model 2 Fisherman Style Fiddler Cap
$36.00
SCALA Crushable Wool Felt Safari Charcoal Safari Hats
$24.75
Brixton Brood Snap Cap Bone Caps
$39.00
Brixton Brood Snap Cap Sandstone Caps
$39.00
elope Jimi Hendrix Costume Hat for Adult Men
$29.95
Mens Womens Flat Top Wool Warm Cap Baseball Hiking Outdoor Army Military Hat
$14.95
Black Leather Deadman Top Hat
$69.00
Brixton Ashland Cap BlackBlack Caps
$44.00
Brixton Fiddler KhakiBrownCream Traditional Hats
$42.00
Brixton Fiddler BrownGrey Traditional Hats
$42.00
Brixton Fiddler Black Herringbone Twill Traditional Hats
$27.06
Raffia Straw Top Hat Fedora - Brown
$34.49
Black Hills Hat
$48.00
1970s Bollman Collection Boogie
$100.00
Runkle Straw Pork Pie
$80.00
1960s Bollman Collection Hippie
$100.00
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1930s Bollman Collection Trilby
$100.00
Planter Hat
$33.00
Dean The Butcher Fedora
$125.00
Creel Litestraw reg Fedora
$120.00
Pork Pie Hat
$218.00
1920s Bollman Collection Fedora
$100.00
1910s Bollman Collection Montana Peak
$100.00
Klaxon
$64.00
Kangol Stripe-Air 504
$50.00
1900s Bollman Collection Homburg
$100.00
1890s Bollman Collection Bowler
$100.00
1880s Bollman Collection Topper
$100.00
1860s Bollman Collection Wide Awake
$100.00
Galvin Plaid Ivy Cap
$85.00
Mens Scala Wool Felt Bowler Hat - Black
$51.00
Janetshats Straw Fedora Unisex Summer Sun Hats Panama Short Brim Hat Men Women
$33.99
Pork Pie Hat-100% Wool Felt Mens Porkpie Hats Flat Mens Fedora Top Classic Bowknot Telescope Cap Outfit Decorations
$25.98
Mens Premium Milano Wool Felt Fedora Grosgrain Band Hat
$39.00
Cotswold Country Hats Homburg Mens Hat - Brown Grey. Stiff Build Lined. Handmade from 100% Wool Felt. Small Medium Large Extra Large XX Large
£36.95
Stetson Saks Homburg Fur Felt Hat Women/Men | Made in The EU Men´s with Lining Grosgrain Band Piping Summer-Winter
£139.00
Pork Pie Milan Panama Natural Straw Hat Dress
$197.45
Jaxon Alpine Fedora Hat
$40.00
Ultrafino Hollywood Gambler Mens Straw Panama Hat
$174.59
SCALA Men’s Dress Straw 1 Piece Boater Hat 10/11mm Laichow Braid Formal Dress Hat
$55.00
Failsworth 100% Irish Linen Alfie Bakerboy Cap
£17.95
Austrian & German Style Alpine Tyrolean Wool Hat With Feather & Rope by E.H.G.
$36.89
Mens Fancy Summer Straw Pork Pie Derby Fedora Upturn Brim Hat
$23.99
ENGLISH OPTIMO Panama Hat Natural Straw Classic
$133.19
ASTRO HATTER Victorian Black Linnig Top Hat
$83.70
Levine Hat Co. Mens Casa Blanca Optimo Crown Panama Straw Dress Hat
$109.00
Original Panama Hat - White Classic Fedora - Black Band - Toquilla Straw - Handwoven in Ecuador by Ecua-Andino
$97.99
Dobbs Kingston - Panama Straw Gambler Hat
$119.98
Olney Traditional Straw Boater - Black Band
£39.99
Jaxon & James Straw Boater Hat - Striped Band
£32.95
Quality Boater Straw Hat
$160.00
CTM Straw 2.5 Inch Brim Boater Hat with Navy Band
$27.94
Cotswold Country Hats Black Wool Felt Homburg Mens Hat S/M/L/XL/XXL
£36.95
DH Hand Made 100% Wool Hard Top Churchill Homburg Felt Trilby Hat New
£27.99
Country Gentleman Mens Fedora
£57.28
Country Gentleman Mens Fedora
£57.28
Stacy Adams Mens Wool Felt Feather Fedora Hat
£60.10
1930 Prohibition Era Hairstyle Book Mens Children Flapper Hairstyles DIY Beautician
$14.99
Scala Classico Mens Felt Homburg Hat Grey Hats L
$56.95
Stetson Fredrick - Wool Fedora Hat
$79.98
Deadwood Trading Portobelo - Fedora Hat
$34.98
Scala Classico Mens Paper Braid Safari Hat Bone Hats XL
$36.95
Scala Classico Mens Toyo Stripe Ribbon Fedora Bone Hats M
$53.95
Tumi Fino rollable/foldable Panama hat fair trade hand woven in Ecuador
£84.95
Traditional Panama hat foldable with BROWN band size 60 - Fair trade and hand woven in Ecuador
£44.95
Stetson Mens Stratoliner Florentine Milan Straw Hat
$82.00
Stetson Wheat Boater Straw Hat Women/Men
$78.82
Stetson Hats Mens Retro 2 1/2 Brim Panama Fashion Hat
$72.98
Great Gatsby in Fashion eBook
$2.99
Flat Cap with Peak Shelby Baker Boy Newsboy Herringbone Cloth Cap Hat
Black Grey Herringbone Newsboy 8 Panel Baker Boy Tweed Flat Cap Mens Gatsby Hat
£13.99
Flat Cap with Peak Shelby Baker Boy Newsboy Herringbone Cloth Cap Hat
Fancet Mens Winter Ivy Newsboy Flat Hunting Gatsby Hat Fall 55-61cm
$19.99
Folie Co. 100% Wool Herringbone Winter Ivy Cabbie Hat w/Fleece Earflaps – Driving Hat
$44.99
John Hanly Men’s Irish Flat Cap 100% Wool Tweed Ear Flap Made in Ireland
$69.95
John Hanly Men’s Irish Flat Cap 100% Wool Tweed Ear Flap Made in Ireland
$69.95
Ace of Spades Gambler Hat
$39.99
Deluxe Felt Black Padre Priest Old Western Spanish Amish Billy Jack Hat Costume
$18.47
ArtiDeco Straw Boater Hat Mens 1920s Mens Gatsby Hat Panama Straw Sun Hats Men Roaring 20s Costume Accesories Men
£15.99
Burnside Mens Long Sleeve Solid Flannel Button Down Shirt B8200
$36.34
Belfry Wool Felt Derby Bowler Hat in Black or Gray
$39.00
Wonderful Fashion Mens Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat (Large/X-Large Charcoal)
$16.98
Belfry Gangster 100% Wool Stain-Resistant Crushable Dress Fedora in 4 Colors
$35.99
Shelby Newsboy Grey Herringbone Cloth Cap By Gamble & Gunn
£22.49
High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
Belfry Bogart Fedora in Black or Navy
$39.00
High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
Alora Wide Brim Boater
$265.00
Pork Pie Hat
$218.00
Different Touch 100% Wool Felt Steampunk Victorian Style Mad Hatter Low Rise Top Hats
$49.99
High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown
$39.95
Belfry John Bull Theater-Quality Men’s Wool Felt Top Hat in Gray or Black
$69.00
Belfry Topper 100% Wool Satin Lined Mens Top Hat in Black Available in 4 Sizes
$39.00
5 Panel Vintage Newsboy Hat
$13.99
Top Hat Beaver
$350.00
Mens Homburg Hat
Linen 8 Panel Applejack Gatsby newsboy IVY Hat
$10.95
Plaid Cap Hat
$19.99
Top Hat Collapsible
$400.00
Biddy Murphy Men’s Irish Fedora 100% Wool Tweed Cap Made in Ireland
$74.95
Hanna Hats Mens Donegal Tweed Original Irish Walking Hat
$59.99
Hanna Hats Mens Donegal Tweed Original Irish Walking Hat
$59.99
Belfry Gangster 100% Wool Stain-Resistant Crushable Dress Fedora in 4 Colors
$39.95
Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown
$39.95
ililily Howels Faux Leather Aviator Trapper Trooper Faux Fur Ear Flaps Hat
$42.49
Cov-ver Hats Australian Wool Steam-Punk Top Hat With Brass Rings
$78.00
Tropical Pith Helmet in British Khaki
$32.95
Steampunk Sunglasses
$24.95
Borges & Scott B&S Premium Doyle - Teardrop Fedora Hat - 100% Wool Felt - Crushable for Travel - Water Resistant - Unisex
£34.95
Borges & Scott B&S Premium Doyle - Teardrop Fedora Hat - 100% Wool Felt - Crushable For Travel - Water Resistant - Unisex
£34.95
Borges & Scott B&S Premium Doyle - Teardrop Fedora Hat - 100% Wool Felt - Crushable for Travel - Water Resistant - Unisex
£34.95
BUTTON VICTORIAN Mad Hatter Tall Top Hat Wool Felt Dress
Conner Hats Mens SteamPunk Top Hat
$80.99
Sun Safari Pith Helmet / White / High Quality
$23.99
Ferrecci Classic Wool Elegant English Mad Hatter Lined Top Hat - MANY COLORS
$54.99
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Natural Top Hat
Wool Greek Fishermans Cap
$48.48
High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
Derby Tweed Flat Cap Hunting Shooting Countrywear Hat
$22.02
Conner Hats Australian Wool Steam-Punk Top Hat
$78.00
Peaky Blinders 8 Piece Newsboy Style Flat Cap -100% Wool
£20.00
Casa Blanca Optimo Panama Straw Dress Hat
$89.00
Adult Train Engineer Cap
$15.95
Dorfman Wool Felt Hat
$44.95
Mens Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat
$16.98
UK- C-Crown Fedora - Grey
£43.95
U.S. WWII Officer Visor Crusher Cap: Winter (OD Green)- Size 7 US 1/2 (60 cm)
$64.95
U.S. WWII Issue Garrison Cap- Infantry & Paratrooper: Size US 7 1/2 60 cm
$29.95
Tumi Genuine Hand Woven Fedora Panama Hat - Rollable
£46.95
Natural Straw Stingy Brim Fedora Mod/Ska Block Black and Lime Band
£16.00
Jaxon & James Straw Boater Hat - Striped Band
£32.95
Gambler Panama Straw Hat
$89.00
Jaxon & James Straw Boater Hat - Striped Band
£32.95
Victorian Dicken MENS Christmas Holiday HAT/bow tie costume accessories
$42.00
Steampunk Deluxe Top Hat With Goggles
$11.63
Mens Derby Tweed Flat Cap Teflon Coated
$23.95
Belfry John Bull Theater-Quality Men’s Wool Felt Top Hat in Gray or Black
$69.00
Wheat Braid Top Hat Fedora - Brown
