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    • Small
      Pequeuño
      Size
      6
      3/4
      -
      6
      7/8
      Tamaño
      21
      1/8
      "
      -
      21
      1/2
      "
      54
      cm
      -
      55
      cm
    • Medium
      Medio
      Size
      7
      -
      7
      1/8
      Tamaño
      21
      7/8
      "
      -
      22
      1/4
      "
      56
      cm
      -
      57
      cm
    • large
      Grande
      Size
      7
      1/4
      -
      7
      3/8
      Tamaño
      22
      5/8
      "
      -
      23
      "
      58
      cm
      -
      59
      cm
    • X-Large
      X-Grande
      Size
      7
      1/2
      -
      7
      5/8
      Tamaño
      23
      1/2
      "
      -
      23
      7/8
      "
      60
      cm
      -
      61
      cm
    • XX-Large
      XX-Grande
      Size
      7
      3/4
      -
      7
      7/8
      Tamaño
      24
      1/4
      "
      -
      24
      5/8
      "
      62
      cm
      -
      63
      cm
    • XXX-Large
      XXX-Grande
      Size
        8
       - 
      8 +
      Tamaño
      25
      "
      -
      25
      3/8
      "
      64
      cm
      -
      65
      cm
  • This is a General Hat Sizing Chart: Please read each hat product page for further sizing information.
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  • Retail (25)

Bailey Teardrop Hats

1 - 25 of 25 Products
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…to look good doing it.   Approx. 4" Teardrop Crown 2 3/8" Brim Made of: 100% Genuine Panama Straw (Cuenca Weave)   Handwoven in Ecuador Blocked & Finished in the USA Double Layer Japanese Grosgrain Ribbon Hat Band Bailey Side Pin Fine Woven Sweatband   Sizes:…

$155.00

…Long Teardrop Fedora Hat by Bailey also boasts a distinctive polished felt finish, resulting in a lustrous finish and silky felt texture. Trimmed with a deluxe Japanese grosgrain ribbon hatband and small Bailey side pin, the Criss Wool Felt Long Teardrop Fedora Hat is a gorgeous addition to your hat

$119.00

…Long Teardrop Fedora Hat by Bailey also boasts a distinctive polished felt finish, resulting in a lustrous finish and silky felt texture. Trimmed with a deluxe Japanese grosgrain ribbon hatband and small Bailey side pin, the Criss Wool Felt Long Teardrop Fedora Hat is a gorgeous addition to your hat

(2)
$130.00

…100% wool felt Ammon Wool Felt Teardrop Fedora Hat by Bailey is astonishingly silky to the touch. A classic teardrop crown (aka C-Crown) and all around down-sloping brim characterize this elegant fedora hat. Finished with a Japanese grosgrain hat band, small Bailey side pin, fine woven sweatband and…

$160.00

…the Freddy Braid Fedora Hat from Bailey! This packable, crushable hat is perfect for travel, and features alightweight  breathable unlined interior with a cotton twill sweatband. Best of all, the heathered build is incredibly comfortable!   Approx. 4" Teardrop Crown 2 1/4" Snap Brim …

$75.00
Available Colors:
  • BLACK
  • RUST

…Panama Straw Fedora Hat from Bailey! This American-made hat is made of fine, reliable panama (toquila palm) straw, complete with a leather hat band and woven detail wrapping around the crown. Quality matters, and Bailey knows that!   Approx. 3 3/4" Teardrop Crown 2 1/4" Down Turned…

$170.00
Available Colors:
  • NATURAL

…durable straw hat in the market.  Showcasing a narrow leather hat band with stitching, as well as a Bailey side pin, this hat is high quality. Plus, the Dri-Lex® absorbent sweatband and unlined interior are very breathable and comfortable.   Approx. 3 3/4" Teardrop Crown 2 1/4" Snap…

$102.00

Hat from Bailey. This light-weight hat features a simple, almost minimalist design, made of durable, comfortable toyo straw, complimented by a single Bailey side label. It's all tied together by a solid stripe of color wrapping around the underside of the brim.   Approx. 3 1/2" Teardrop

$78.00
Available Colors:
  • NATURAL
  • BROWN

  Introducing the Bailey Wilshire Toyo Braid Straw Fedora Hat with the gorgeous collection of colors to grab your eye and the lovely rounded teardrop crown will make this hat your new favorite everyday hat.   Approx. 4" Rounded Teardrop Crown 2" Snap Brim   Made of: 50% Toyo…

$68.00
Available Colors:
  • COPPER

Made in the USA The Bailey Guthrie is made of a new softening and finishing technology for Shantung Straw which creates an incredibly comfortable and flexible fit. As an added bonus, this is one of the few straw hats that is actually water resistant. The hat comes with the Dri-Lex moisture…

(3)
$130.00
Available Colors:
  • NATURALBLACK

…shape retentive, durable straw hat in the market. This durable hat features a faux leather braided hat band, as well as a Bailey side pin. Made in America, this hat is absolutely high quality!   Approx. 3 1/2" Teardrop Crown - Front 3 3/4" Teardrop Crown - Back 2 1/4" Turn Down Brim …

$120.00
Available Colors:
  • IVORY
  • NATURAL

…action, the Bailey of Hollywood Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This short snap-brim braided straw hat is soft and packable for your convenience, but powerful and eye-grabbing in regards to looks and style.   The teardrop crown…

$56.10

…action, the Bailey of Hollywood Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This short snap-brim braided straw hat is soft and packable for your convenience, but powerful and eye-grabbing in regards to looks and style.   The teardrop crown…

(6)
$66.00

…  Handmade in the USA, Bailey's Lund LiteFelt Wool Fedora Hat has been crafted from LiteFelt wool, which is water repellent and shape retentive. A signature shape with a long teardrop crown and snap brim, the Lund also features a suede braid cording hat band. This hat band has been threaded…

$125.00
Available Colors:
  • BURNTORANGE

  Made in the USA The Bailey Wynn Wool Felt Fedora Hat is a simple yet elegant hat.  This hat has been factory treated and is water and stain resistant.   Approx. 3 7/8" Teardrop crown 1 1/2" Pre-Snap Brim (Front) 1" Curled Brim (Sides & Back)   Made of: 100%…

(1)
$93.00

  Introducing the Bailey Wilshire Toyo Braid Straw Fedora Hat with the gorgeous collection of colors to grab your eye and the lovely rounded teardrop crown will make this hat your new favorite everyday hat.   Approx. 4" Rounded Teardrop Crown 2" Snap Brim   Made of: 50% Toyo…

$80.00
Available Colors:
  • BLACK
  • NAVYBLUE
  • SAND

…Note: Due to different shipments from Bailey, hats may either have a Bailey pin or a Bailey tag on the hat band. Welcome to today's hot new look in an amazingly soft, packable, and comfortable sewn braid! The Bailey Billy Braided Toyo Straw Fedora Hat is a top selling topper with a stingy…

$56.10
Available Colors:
  • BLUE

…Note: Due to different shipments from Bailey, hats may either have a Bailey pin or a Bailey tag on the hat band. Welcome to today's hot new look in an amazingly soft, packable, and comfortable sewn braid! The Bailey Billy Braided Toyo Straw Fedora Hat is a top selling topper with a stingy…

$56.10
Available Colors:
  • NAVYRED
  • BLACKGOLD

…comfortable, you'll always be enjoying this hat!   Approx. 4" Teardrop Crown - Front 3 3/4" Teardrop Crown - Back 2 3/4" Snap Brim   Made of: 55% Toyo Straw 45% Polyester   Grosgrain Ribbon Hat Band Narrow Leather Hat Band Bailey Side Label Cotton Twill Sweatband…

$83.00
Available Colors:
  • BLACK
  • LATTE

…the Bailey Archer Toyo Straw Braid Fedora Hat with a stingy (short) snap brim for a sleek look. Crafted of a lightweight and flexible toyo straw blend, the Archer is a great alternative to classic straw fedoras that are prone to cracking and crushing.    Approx. 3 3/8" Teardrop Crown…

(1)
$75.00
Available Colors:
  • SMOKE
  • COFFEE

…action, the Bailey of Hollywood Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This short snap-brim braided straw hat is soft and packable for your convenience, but powerful and eye-grabbing in regards to looks and style.   The teardrop crown…

$66.00
Available Colors:
  • WINE

…Note: Due to different shipments from Bailey, hats may either have a Bailey pin or a Bailey tag on the hat band. Welcome to today's hot new look in an amazingly soft, packable, and comfortable sewn braid! The Bailey Billy Braided Toyo Straw Fedora Hat is a top selling topper with a stingy…

$66.00

…Note: Due to different shipments from Bailey, hats may either have a Bailey pin or a Bailey tag on the hat band. Welcome to today's hot new look in an amazingly soft, packable, and comfortable sewn braid! The Bailey Billy Braided Toyo Straw Fedora Hat is a top selling topper with a stingy…

(26)
$66.00

…Made in the USA   Bailey's Delmark Elite Finish Wool Felt Fedora Hat is a 100% 16 micron sheep's wool felt fedora made in the USA! Vintage-inspired with a raised front teardrop crown and a slightly flared brim, this hat also features a genuine leather hat band with a decorative woven…

$161.50
Available Colors:
  • DARKBROWN
  • STONE

…Wool Felt Western Hat by Bailey. Whether you are going for the Union Blue or Conferdate gray you have both options with this hat. It is very stiff and sturdy so you won't have to worry about it being flimsy while you are going into battle.   Approx. 4 1/2" Teardrop Crown  3 1/2" Raw Edge…

(2)
$110.00

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