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Bailey Bailey Bailey

Bailey

Ready to add some timeless style to your wardrobe? A Bailey men’s hat is just the way to do it. Styles from this classic hat-maker have stood the test of time and continue to be popular choices for men’s fashion.

The Bailey Brand

Built upon a nearly century-old legacy of Hollywood and the New West, Bailey hats embody the spirit of fashionable, functional headwear that evolved out of 1920s Los Angeles. Hat-maker George Bailey initially started the small hat company to cater to ranchers and business people in Southern California. But eventually, his signature styles gained popularity among celebrities like Humphrey Bogart, Gary Cooper and Bing Crosby. The Bailey hat is known for its exceptional craftsmanship and attention to detail, with styles made from quality materials like fur felt, leather and genuine Panama straw.

Selection Meets Style

At Hats in the Belfry, we carry all of the most popular Bailey hats, including a huge selection of Bailey fedoras made from lightweight straw, luxurious wool felt and other long-lasting materials. Bailey even offers a selection of waterproof fedoras as well as packable fedoras designed for modern travel. You’ll also find a variety of Bailey ivy caps, safari hats and newsboy caps from this iconic hat-maker. And if you’ve been searching for a pork pie hat with an updated, modern style, Bailey’s is the perfect brand for you. Browse our full collection of Bailey’s men’s hats to find a great new look with a hint of classic Hollywood style.
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  • Bailey Tino - Wool Felt Fedora Hat

    Bailey Tino

    Wool Felt Fedora Hat

    color:

    Blackbrown

    Price: $78.00
  • Bailey Port - Packable Ivy Cap

    Bailey Port

    Packable Ivy Cap

    color:

    gry/brn

    Price: $50.00
  • Bailey Dalton - Canvas Safari Rain Hat

    Bailey Dalton

    Canvas Safari Rain Hat

    color:

    Blackbrown

    Price: $55.00
  • Bailey Yates - Water Repellent Wool Fedora

    Bailey Yates

    Water Repellent Wool Fedora

    color:

    Pewter

    Price: $90.00
  • Bailey Perry - Lanolux Wool Felt Fedora

    Bailey Perry

    Lanolux Wool Felt Fedora

    color:

    AshNavytobacco

    Price: $120.00
  • Bailey Vito - Packable Lightweight Fedora

    Bailey Vito

    Packable Lightweight Fedora

    color:

    Blk MixCopperNavy

    Price: $70.00
  • Bailey Ormond - Paneled Ivy Cap

    Bailey Ormond

    Paneled Ivy Cap

    color:

    Black

    Price: $55.00
  • Bailey Leander - Cotton & Leather Ivy Cap

    Bailey Leander

    Cotton & Leather Ivy Cap

    color:

    brown

    Price: $65.00
  • Bailey Ragon - Paper Braid Stingy Brim Fedora

    Bailey Ragon

    Paper Braid Stingy Brim Fedora

    color:

    Forest

    Price: $70.00
  • Bailey Oran - Sueded Leather Ivy Cap

    Bailey Oran

    Sueded Leather Ivy Cap

    color:

    Grey

    Regular Price: $99.00

    Special Price: $73.00

  • Bailey Hopper - Wool Cattleman Fedora

    Bailey Hopper

    Wool Cattleman Fedora

    color:

    Black

    Regular Price: $149.00

    Special Price: $126.65

  • Bailey Haskin - Sueded Wool Felt Fedora

    Bailey Haskin

    Sueded Wool Felt Fedora

    color:

    Asphalt

    Regular Price: $149.00

    Special Price: $126.65

  • Bailey Sheldon - Plaid Wool Flat Cap

    Bailey Sheldon

    Plaid Wool Flat Cap

    color:

    Blue

    Regular Price: $89.00

    Special Price: $59.50

  • Bailey Lord - Classic Wool Ivy Cap

    Bailey Lord

    Classic Wool Ivy Cap

    color:

    Charcoal

    Regular Price: $79.00

    Special Price: $63.75

  • Bailey Salem - Braided Classic Fedora

    Bailey Salem

    Braided Classic Fedora

    color:

    DriftwdNaturalNavy

    Price: $60.00
  • Bailey Mannesroe - Contemporary Fedora

    Bailey Mannesroe

    Contemporary Fedora

    color:

    blk/charIvy/Adob

    Price: $60.00
  • Bailey Archer - Crushable Paperbraid Fedora

    Bailey Archer

    Crushable Paperbraid Fedora

    color:

    Smoke

    Price: $68.00
  • Bailey Egan - Linen Ivy Cap

    Bailey Egan

    Linen Ivy Cap

    color:

    Oyster

    Price: $65.00
  • Bailey Billy - Crushable Paperbraid Fedora

    Bailey Billy

    Crushable Paperbraid Fedora

    color:

    Latte

    Price: $60.00
  • Bailey Mannes - Multi-Braid Fedora

    Bailey Mannes

    Multi-Braid Fedora

    color:

    Char MulMilitaryNat Multnavy mul

    Regular Price: $60.00

    Special Price: $43.00

  • Bailey Redford - Cotton 8/4 Cap

    Bailey Redford

    Cotton 8/4 Cap

    color:

    Cream/Burnt Stripe

    Price: $55.00
  • Bailey Niven - Cuenca Panama Fedora

    Bailey Niven

    Cuenca Panama Fedora

    color:

    Sien/Nat

    Regular Price: $138.00

    Special Price: $57.00

  • Bailey Waits - Poly Braid Pork Pie Hat

    Bailey Waits

    Poly Braid Pork Pie Hat

    color:

    CopperSteel

    Price: $70.00
  • Bailey Jackman - Packable Wool Felt Fedora

    Bailey Jackman

    Packable Wool Felt Fedora

    color:

    CharcoalWoodland

    Regular Price: $105.00

    Special Price: $98.00