Men’s vintage style hats in classic shapes such as a wide brim fedora, bowler or derby, straw panama, gambler, homburg, flat cap, or straw boater. Each decade had their favorite styles with minor changes in brim width, band color, crown crease, and straw weave. Vintage men’s hats are highly collectible and quite expensive. Learn about each men’s vintage hats by decade: 1920s, 1930s, 1940s, 1950s, 1960s-1970s
Find your perfect new vintage style hat below from multiple retailers online. Be sure to take your correct head-size measurement before ordering.
Men’s Vintage Style Hats
SCALA Straw Boater with Two-Tone Stripe Grosgrain Ribbon Bleach Caps
$27.90
Shelby Tweed News Boy Cap
£54.17
Frederick Fedora
$60.00
Big Boss Homburg - Exclusive
$39.99
UK- High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
Linen 8 Panel Applejack Gatsby newsboy IVY Hat
$10.95
Mens Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat
$16.98
Belfry Gangster 100% Wool Stain-Resistant Crushable Dress Fedora in 4 Colors
$35.99
High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
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
The Great Gatsby in Fashion eBook
$2.99
Frederick Fedora
$60.00
Belfry Wool Felt Derby Bowler Hat in Black or Gray
$39.00
Frederick Fedora
$60.00
Black Leather Deadman Top Hat
$69.00
Mens Homburg Hat
Plaid Cap Hat
$19.99
Belfry John Bull Theater-Quality Men’s Wool Felt Top Hat in Gray or Black
$69.00
High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
Failsworth 100% Irish Linen Alfie Bakerboy Cap
£17.95
Sterkowski Maciejówka Model 2 Fisherman Style Fiddler Cap
$36.00
Shelby Newsboy Grey Herringbone Cloth Cap By Gamble & Gunn
£22.49
DH Hand Made 100% Wool Hard Top Churchill Homburg Felt Trilby Hat New
£27.99
Caufields Brown Steampunk Hat with Black StrapsOne Size
$24.99
1890s Bollman Collection Bowler
$100.00
Jaxon & James Straw Boater Hat - Striped Band
£32.95
Danger Pork Pie - Exclusive
$39.99
1900s Bollman Collection Homburg
$100.00
Borges & Scott B&S Premium Doyle - Teardrop Fedora Hat - 100% Wool Felt - Crushable For Travel - Water Resistant - Unisex
£34.95
BOTVELA Mens Premium Wool Classic Flat Ivy Newsboy Cap Herringbone Pattern Flecked Hat
$29.99
Frederick Fedora
$60.00
UK- C-Crown Fedora - Grey
£43.95
Dobell Mens Black Top Hat 100% Wool Formal Wedding Races
£39.99
Quality Boater Straw Hat
$160.00
5 Panel Vintage Newsboy Hat
$13.99
Top Hat Collapsible
$400.00
Frederick Fedora
$60.00
Robin Litefelt reg Fedora
$105.00
Frederick Fedora
$60.00
Biddy Murphy Irish Tweed Caps 100% Wool Charcoal Herringbone Made in Ireland
$84.99
Deadwood Trading Portobelo - Fedora Hat
$34.98
Ferrecci Classic Wool Elegant English Mad Hatter Lined Top Hat - MANY COLORS
$54.99
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
Men’s Newsboy Gatsby Hat Vintage Beret Flat Ivy Cabbie Driving Hunting Cap for Boyfriend Gift
$29.99
Country Gentleman Mens Fedora
£57.28
Flat Cap with Peak Shelby Baker Boy Newsboy Herringbone Cloth Cap Hat
Top Hat Beaver
$350.00
Stacy Adams Polybraid Pinch Front Fedora with Silk Band Cognac Fedora Hats
$22.50
1880s Bollman Collection Topper
$100.00
Flat Cap with Peak Shelby Baker Boy Newsboy Herringbone Cloth Cap Hat
Dorfman Wool Felt Hat
$44.95
Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown and Striped Bands
$39.95
Olney Traditional Straw Boater - Black Band
£39.99
Tumi Fino rollable/foldable Panama hat fair trade hand woven in Ecuador
£84.95
High Quality Crushable Hand Made Gents Indiana 100% Wool Felt Fedora Trilby Hat With Wide Band
£25.99
Derby Hat
$110.00
Country Gentleman Mens Fedora
£57.28
BRIXTON Mens Brood Newsboy Snap Hat
$37.11
Mens Top Hat Satin Lined Topper by Belfry 100% Wool in Black Grey Navy Pearl
$39.95
Wool Greek Fishermans Cap
$48.48
Belfry Bowler Derby 100% Pure Wool Theater Quality Hat in Black Brown Grey Navy Pearl Green
$39.95
1930 Prohibition Era Hairstyle Book Mens Children Flapper Hairstyles DIY Beautician
$14.99
Borges & Scott B&S Premium Doyle - Teardrop Fedora Hat - 100% Wool Felt - Crushable for Travel - Water Resistant - Unisex
£34.95
Conner Hats Australian Wool Steam-Punk Top Hat
$78.00
Casa Blanca Optimo Panama Straw Dress Hat
$89.00
30s 20s navy blue CAP cotton linen blend swing lindy hop 1930 1920
$113.04
Elope John Bull Low Steampunk Top Hat in Brown
$35.25
elope Jimi Hendrix Costume Hat for Adult Men
$29.95
1960s Bollman Collection Hippie
$100.00
SCALA Men’s Dress Straw 1 Piece Boater Hat 10/11mm Laichow Braid Formal Dress Hat
$55.00
Stetson Saks Homburg Fur Felt Hat Women/Men | Made in The EU Men´s with Lining Grosgrain Band Piping Summer-Winter
£139.00
CTM Straw 2.5 Inch Brim Boater Hat with Navy Band
$27.94
Stacy Adams Mens Wool Felt Feather Fedora Hat
£60.10
Belfry Bogart Fedora in Black or Navy
$39.00
Belfry Gangster 100% Wool Stain-Resistant Crushable Dress Fedora in 4 Colors
$39.95
Derby Tweed Flat Cap Hunting Shooting Countrywear Hat
$22.02
Jaxon & James Straw Boater Hat - Striped Band
£32.95
Mens Derby Tweed Flat Cap Teflon Coated
$23.95
Baldwin Pork Pie
$40.00
Big Boss Homburg - Exclusive
$39.99
Epoch Mens Classic 8 Panel Wool Blend newsboy Snap Brim Collection Hat
Blixen LiteFelt Fedora
$98.00
Lieutenant Cap
$38.00
Mens Womens Flat Top Wool Warm Cap Baseball Hiking Outdoor Army Military Hat
$14.95
Wonderful Fashion Mens Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat (Large/X-Large Charcoal)
$16.98
Belfry Topper 100% Wool Satin Lined Mens Top Hat in Black Available in 4 Sizes
$39.00
Biddy Murphy Men’s Irish Fedora 100% Wool Tweed Cap Made in Ireland
$74.95
BUTTON VICTORIAN Mad Hatter Tall Top Hat Wool Felt Dress
Wheat Braid Top Hat Fedora - Brown
Brcus Men Women Yacht Captain Sailor Hat Newsboy Cabbie Baker Boy Peaked Beret Cap
$12.99
Big Boss Homburg - Exclusive
$39.99
Historical Emporium Mens Deluxe Velvet Embroidered Smoking Cap
$49.95
Ace of Spades Gambler Hat - Exclusive
$39.99
Historical Emporium Mens British Empire Pith Helmet
$44.95
Black Hills Hat
$48.00
1930s Bollman Collection Trilby
$100.00
Peaky Blinders 8 Piece Newsboy Style Flat Cap -100% Wool
£20.00
Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora in Black Grey Navy Brown Pecan
$44.95
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Planter Hat
$33.00
1860s Bollman Collection Wide Awake
$100.00
Folie Co. 100% Wool Herringbone Winter Ivy Cabbie Hat w/Fleece Earflaps – Driving Hat
$44.99
Different Touch 100% Wool Felt Steampunk Victorian Style Mad Hatter Low Rise Top Hats
$49.99
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
Natural Top Hat
Sun Safari Pith Helmet / White / High Quality
$23.99
Retro Style Nautical Straw Striped Ribbon Boater Hat
$32.00
Bailey Kenrick - Wool Porkpie Hat
$57.50
Britten Newsboy
$36.00
Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown and Striped Bands
$39.95
Derby Hat
$110.00
Quest Safari Fedora - Exclusive
$39.99
Trinidad Panama Boater
$108.50
CHARM Mens Summer Beanie Cotton - Womens Crochet Slouch Cap Hand Made Chemo Hat
$17.00
Dean The Butcher Fedora
$125.00
Klaxon
$64.00
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
Black Grey Herringbone Newsboy 8 Panel Baker Boy Tweed Flat Cap Mens Gatsby Hat
£13.99
Burnside Mens Long Sleeve Solid Flannel Button Down Shirt B8200
$36.34
Cov-ver Hats Australian Wool Steam-Punk Top Hat With Brass Rings
$78.00
Rubies Straw Sailor Hat Skimmer Boater Amish Costume Accessory Hat Medium Large
$41.95
Dobbs Wellington - Linen 84 Cap
$49.98
Larkin LiteStraw Pork Pie
$112.50
Fisherman Cap
$35.00
Argo Wool Fiddler Cap
$18.75
Cowpuncher Western Hat
$120.00
Charm Men Summer Beanie Knit - Women Hipster Slouchy Hat Boho Street Fashion Cap
$20.20
Brixton Brood Snap Cap Bone Caps
$39.00
Brixton Fiddler Black Herringbone Twill Traditional Hats
$42.00
Galvin Plaid Ivy Cap
$85.00
1970s Bollman Collection Boogie
$100.00
Mens Premium Milano Wool Felt Fedora Grosgrain Band Hat
$39.00
Pork Pie Milan Panama Natural Straw Hat Dress
$197.45
Original Panama Hat - White Classic Fedora - Black Band - Toquilla Straw - Handwoven in Ecuador by Ecua-Andino
$97.99
Traditional Panama hat foldable with BROWN band size 60 - Fair trade and hand woven in Ecuador
£44.95
SATINIOR White Sailor Hats Navy Captain Hats Yacht Hat for Teens and Adults Costume
$7.59
Joey Braided Fedora
$43.00
Salem Braided Fedora
$66.00
Darron LiteFelt Pork Pie
$95.00
Olin Fedora
$350.00
Scala Panama Boater Cherry Hill - Straw Boater Hat
$140.00
Brixton Fiddler KhakiBrownCream Traditional Hats
$42.00
Brixton Brood Snap Cap Sandstone Caps
$39.00
Ultrafino Hollywood Gambler Mens Straw Panama Hat
$174.59
Jaxon Alpine Fedora Hat
$40.00
Ace of Spades Gambler Hat
$39.99
Borges & Scott B&S Premium Doyle - Teardrop Fedora Hat - 100% Wool Felt - Crushable for Travel - Water Resistant - Unisex
£34.95
Adult Train Engineer Cap
$15.95
Belfry John Bull Theater-Quality Men’s Wool Felt Top Hat in Gray or Black
$69.00
Beelittle Yacht Captain Hat Costume Accessories Set Sailor Hat with Corn Cob Pipe & Aviator Sunglasses
$15.99
Chiclinco Admiral Captain Yacht Hat with Adjustable Snapback & Gold Embroidery Anchor Skippers Cap for Club Pub Party Costume Accessory (White)
$17.90
Wool Arnold
$48.75
Dobell Mens Black Top Hat 100% Wool Formal Wedding Races
$69.95
Wind River by Bailey Columbia LiteFelt Outback
$88.00
Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora in Black Grey Navy Brown Pecan
$44.95
Lord Plaid Ivy Cap
$85.00
Levoy
$60.00
Maglor Fedora
$59.00
Brixton Brood Snap Cap GreyTan Plaid Caps
$39.00
Mens Rounded Top 1 Wool 4 Inches High Crown Dark Brown Hat
$59.00
Creel Litestraw reg Fedora
$120.00
Cowpuncher Western Hat
$120.00
KUYOU Womens Multifunction Plus Cashmere Hat Skull Cap Scarf
$9.99
Creel Litestraw reg Fedora
$120.00
Cotswold Country Hats Black Wool Felt Homburg Mens Hat S/M/L/XL/XXL
£36.95
Scala Classico Mens Paper Braid Safari Hat Bone Hats XL
$36.95
Scala Classico Mens Felt Homburg Hat Grey Hats L
$60.95
Stetson Wheat Boater Straw Hat Women/Men
$78.82
Fancet Mens Winter Ivy Newsboy Flat Hunting Gatsby Hat Fall 55-61cm
$19.99
Belfry Crushable Dress Fedora Mens Vintage Style Hat 100% Pure Wool in Black Blue Grey Pecan Brown
$39.95
Steampunk Sunglasses
$24.95
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
Tigerdoe Steampunk Halloween Costumes - Steampunk Hat with Goggles - Steampunk Accessories - Gentleman’s Costume
Tigerdoe Yacht Captain Hats - Marine Sailor Caps - Skipper Party - Nautical Costume Accessories
Retro Visor
$40.00
Pendleton LS Board Shirt Brown MixIvory Ombre Mens Long Sleeve Button Up
$75.24
Joey Braided Fedora
$43.00
Wool Hawker
$60.00
Wool Twill Fisherman
$54.00
Hamilton GentleFelt Fedora
$65.00
1880s Bollman Collection Topper
$100.00
Mens Headbands vintage trim woven yellow orange green & cream hippie headbands 70s vintage style guys headbands mens headbands Boho style
$17.00
Raffia Straw Top Hat Fedora - Brown
$34.49
Runkle Straw Pork Pie
$80.00
Kangol Stripe-Air 504
$50.00
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
ENGLISH OPTIMO Panama Hat Natural Straw Classic
$133.19
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
ASTRO HATTER Victorian Black Linnig Top Hat
$83.70
Levine Hat Co. Mens Casa Blanca Optimo Crown Panama Straw Dress Hat
$109.00
Stetson Fredrick - Wool Fedora Hat
$79.98
Stetson Hats Mens Retro 2 1/2 Brim Panama Fashion Hat
$72.98
John Hanly Men’s Irish Flat Cap 100% Wool Tweed Ear Flap Made in Ireland
$69.95
Deluxe Felt Black Padre Priest Old Western Spanish Amish Billy Jack Hat Costume
$18.47
- Show More
ArtiDeco Straw Boater Hat Mens 1920s Mens Gatsby Hat Panama Straw Sun Hats Men Roaring 20s Costume Accesories Men
£15.99
Alora Wide Brim Boater
$265.00
Hanna Hats Mens Donegal Tweed Original Irish Walking Hat
$59.99
Conner Hats Mens SteamPunk Top Hat
$80.99
Jaxon & James Straw Boater Hat - Striped Band
£32.95
Gambler Panama Straw Hat
$89.00
Steampunk Deluxe Top Hat With Goggles
$11.63
Broner Yacht Rock Patterned Print Yacht Cap
$25.99
Wall2Wall Captains Yacht Sailors Hat Snapback Adjustable Sea Cap Navy Costume Accessory
$7.95
Tigerdoe Yacht Hats - 3 Pack - Captains Hat - Neon Captain Hat - Boaters Hats - Costume Hats - Novelty Hats
Broner Yacht Rock Patterned Print Yacht Cap
$25.99
Retro Visor
$40.00
Joey Braided Fedora
$43.00
Runkle Straw Pork Pie
$48.00
Wool Enfield
$61.00
Runkle Straw Pork Pie
$48.00
1920s Bollman Collection Fedora
$100.00
Pork Pie Hat
$218.00
Scala Classico Mens Toyo Stripe Ribbon Fedora Bone Hats M
$54.95
John Hanly Men’s Irish Flat Cap 100% Wool Tweed Ear Flap Made in Ireland
$69.95
Hanna Hats Mens Donegal Tweed Original Irish Walking Hat
$59.99
Tropical Pith Helmet in British Khaki
$32.95
Elliot Trilby
$65.00
Gravity Trading 80s/90s Hip-Hop Costume Kit (Bucket Hat + Old School Squared Glasses)
$19.99
Fanny Pack hat | 80s/90s Nylon Cap for Men & Women | Zipper Pocket & Adjustable
$19.99
Fanny Pack hat | 80s/90s Nylon Cap for Men & Women | Zipper Pocket & Adjustable
$19.99
80s Party Fedora Paint Splatter
$9.08
The Bobcat Mullet
$9.99
Fanny Pack hat | 80s/90s Nylon Cap for Men & Women | Zipper Pocket & Adjustable
$19.99
Retro Visor
$40.00
Men39s Chino Bucket Hat - Goodfellow 38 Co8482 Khaki
$17.99
Men39 MTV Flat Brim Baeball Hat - Neon
$14.99
AEO Translucent Visor Mens Neon Orange One Size
$7.18
Vans BMX Hat True Navy Caps
$30.00
Steampunk Top Hat Ring Holder
$18.35
1980s Bollman Collection Urban Western
$100.00
Thurman Panama Fedora
$155.00
Salem Braided Fedora
$66.00
Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora in Black Grey Navy Brown Pecan
Darron LiteFelt reg Pork Pie
$95.00
Hamilton GentleFelt Fedora
$65.00
Stetson Mens Stratoliner Florentine Milan Straw Hat
$82.00
Pork Pie Hat
$218.00
Natural Straw Stingy Brim Fedora Mod/Ska Block Black and Lime Band
£16.00
