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  • Bailey Hats & Caps

Bailey Hats & Caps

The Bailey Hat Company was founded in 1922 in Los Angeles, California. The company was founded by George S. Bailey who believed that being in LA would allow them to provide hats to all the stars of the Silver Screen and the trendsetters in Hollywood. The population on the west coast was quickly growing and Bailey was at the forefront, creating luxurious styles for everyone from California ranchers and oil tycoons, to businessmen and movie stars. They dressed some of the top Hollywood stars including Humphrey Bogart, Cary Grant, and Gary Cooper who all wore Bailey hats which cemented Bailey as Hollywood's premiere milliner. Today their hats are trendy and affordable with many still produced here in the US.

Bailey Hats are known for the craftsmanship of the product. The quality is apparent in all styles and fabrics including fur felt, leather, wool felt, Litefelt®, Panama straw, and cloth. Bailey Hats are durable; many of their hat products provide good protection in most weather conditions.

Staying true to its history of fine craftsmanship and detailing, the Bailey brand continues to evolve in design. Bailey features classic and contemporary styling.

DelMonico Hatter has a full collection of Bailey Hats and Caps. Select your style!

Bailey Fall & Winter Hats
Bailey Spring & Summer Hats
Bailey Fedora Hats & Dress Hats
Bailey Outdoor Hats
Bailey Caps
Bailey Panama Hats & Straw Hats
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  • All
Bailey Tino Litefelt Hat

Bailey Tino Litefelt Hat

$118.00

Bailey Vega Trapper Hat

Bailey Vega Trapper Hat

$160.00

Bailey Briar Hat

Bailey Briar Hat

$120.00

Bailey Brandt Downbrim Hat

Bailey Brandt Downbrim Hat

$155.00

Bailey Curtis Hat

Bailey Curtis Hat

$118.00

Bailey Gangster Wool Felt Hat

Bailey Gangster Wool Felt Hat

$130.00

Bailey Godfather Hat

Bailey Godfather Hat

$130.00

Bailey Dalton Rain Safari Hat

Bailey Dalton Rain Safari Hat

$75.00

Bailey Cutler Panama Hat

Bailey Cutler Panama Hat

$190.00

Bailey Brooks Panama Hat

Bailey Brooks Panama Hat

$200.00

Bailey Spencer Litestraw Hat

Bailey Spencer Litestraw Hat

$115.00

Bailey Perry Hat

Bailey Perry Hat

$145.00

Bailey Lord Wool Ivy Cap

Bailey Lord Wool Ivy Cap

$88.00

Bailey Derby Wool Felt Hat

Bailey Derby Wool Felt Hat

$135.00

Bailey Litefelt Fedora

Bailey Litefelt Fedora

$118.00

Bailey Stockton Leather Ivy Cap

Bailey Stockton Leather Ivy Cap

$135.00

Bailey Blackburn Litestraw Fedora

Bailey Blackburn Litestraw Fedora

$180.00

Bailey Billy Packable Hat

Bailey Billy Packable Hat

$85.00

Bailey Mannes Hat

Bailey Mannes Hat

$85.00

Bailey Salem Packable Hat

Bailey Salem Packable Hat

$85.00

Bailey Lord Nailhead Tweed Cap

Bailey Lord Nailhead Tweed Cap

$90.00

Bailey Lord Ivy Style Herringbone Cap

Bailey Lord Ivy Style Herringbone Cap

$90.00

Bailey Mannesroe Hat

Bailey Mannesroe Hat

$85.00

Bailey Blixen Hat

Bailey Blixen Hat

$118.00

Bailey Slater Cap

Bailey Slater Cap

$75.00

Bailey Harker Derby Hat

Bailey Harker Derby Hat

$125.00

Bailey Darron Hat

Bailey Darron Hat

$118.00

Bailey Lazar Cap

Bailey Lazar Cap

$110.00

Bailey Yates Hat

Bailey Yates Hat

$95.00

Bailey Berle Straw Fedora

Bailey Berle Straw Fedora

$95.00

Bailey Salter Genuine Panama Fedora

Bailey Salter Genuine Panama Fedora

$350.00

Bailey Wynn Hat

Bailey Wynn Hat

$118.00

Bailey Graham Cap

Bailey Graham Cap

$65.00

Bailey Hanson Shantung Hat

Bailey Hanson Shantung Hat

$165.00

Bailey Thurman Panama Hat

Bailey Thurman Panama Hat

$155.00

Bailey Wilshire Hat

Bailey Wilshire Hat

$80.00

Bailey Langham Cap

Bailey Langham Cap

$138.00

Bailey Ormond Cap

Bailey Ormond Cap

$70.00

Bailey Archer Braid Fedora

Bailey Archer Braid Fedora

$75.00

Bailey Waits Braid Porkpie Hat

Bailey Waits Braid Porkpie Hat

$95.00

Bailey Chaplin Bowler Hat

Bailey Chaplin Bowler Hat

$200.00

Bailey Galvin Herringbone Newsboy Cap

Bailey Galvin Herringbone Newsboy Cap

$100.00

Bailey Lord Plaid Ivy Cap

Bailey Lord Plaid Ivy Cap

$90.00

Bailey Shupp II Ascot Cap

Bailey Shupp II Ascot Cap

$65.00

Bailey Guthrie Litestraw Hat

Bailey Guthrie Litestraw Hat

$165.00

Bailey Roll Up II Hat

Bailey Roll Up II Hat

$240.00

Bailey Bogan Fedora

Bailey Bogan Fedora

$175.00

Bailey Winters Hat

Bailey Winters Hat

$175.00

Bailey Lord Windowpane Plaid Cap

Bailey Lord Windowpane Plaid Cap

$90.00

Bailey Criss Hat

Bailey Criss Hat

$155.00

Bailey Draper III Fedora Hat

Bailey Draper III Fedora Hat

$350.00

Bailey Elliott Trilby Hat

Bailey Elliott Trilby Hat

$75.00

Bailey Foley Braided Straw Fedora

Bailey Foley Braided Straw Fedora

$95.00

Bailey Noclin Leather Newsboy Cap

Bailey Noclin Leather Newsboy Cap

$140.00

Bailey Halpern Panama Fedora

Bailey Halpern Panama Fedora

$165.00

Bailey Tessier Panama Fedora

Bailey Tessier Panama Fedora

$190.00

Bailey Giger Panama Fedora

Bailey Giger Panama Fedora

$200.00

Bailey Klaxon Wool Felt Pork Pie Hat

Bailey Klaxon Wool Felt Pork Pie Hat

$75.00

Bailey Jackman Hat

Bailey Jackman Hat

$135.00

Bailey Groff Genuine Panama Fedora

Bailey Groff Genuine Panama Fedora

$225.00

Bailey Pencer Shantung Litestraw Fedora

Bailey Pencer Shantung Litestraw Fedora

$110.00

Bailey Craig Braided Fedora

Bailey Craig Braided Fedora

$85.00

Bailey Colver Felt Fedora

Bailey Colver Felt Fedora

$185.00

Bailey Salko Dockman Cap

Bailey Salko Dockman Cap

$80.00

Bailey Keter Ivy Cap

Bailey Keter Ivy Cap

$75.00

Bailey Flume Velour Fur Felt Fedora

Bailey Flume Velour Fur Felt Fedora

$350.00

Bailey Shawk Newsboy Cap

Bailey Shawk Newsboy Cap

$60.00

Bailey Derian Endura Straw Hat

Bailey Derian Endura Straw Hat

$135.00

Bailey Tate Braided Fedora

Bailey Tate Braided Fedora

$80.00

Bailey Mullan Braided Fedora

Bailey Mullan Braided Fedora

$100.00

Bailey Rockett Endura Telescope Crown Hat

Bailey Rockett Endura Telescope Crown Hat

$130.00

Bailey Cuban Genuine Panama Hat

Bailey Cuban Genuine Panama Hat

$205.00

Bailey Ardit Panama Hat

Bailey Ardit Panama Hat

$160.00

Bailey Parson Panama Hat

Bailey Parson Panama Hat

$200.00

Bailey Melton Seagrass Gambler Hat

Bailey Melton Seagrass Gambler Hat

$145.00

Bailey Hester Toyo Braid Fedora

Bailey Hester Toyo Braid Fedora

$100.00

Bailey Carver Straw Porkpie

Bailey Carver Straw Porkpie

$80.00

Bailey Stansfield Downbrim Panama Hat

Bailey Stansfield Downbrim Panama Hat

$200.00

Bailey Bevers Litestraw Fedora

Bailey Bevers Litestraw Fedora

$175.00

Bailey Lord Wool Twill Ivy Cap

Bailey Lord Wool Twill Ivy Cap

$90.00

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    New Haven, CT 06510
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