Skip to main content
    • 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.
FREE USA GROUND SHIPPING
FREE USA GROUND SHIPPING
Save Up To $15 | Earth Day Sale | CODE: EARTH
Save Up To $15 | Earth Day Sale | CODE: EARTH
  • Retail (67)

Bailey Teardrop Hats

1 - 28 of 67 Products
View: Grid | List
Sort by

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 hat band and small Bailey side pin, the Criss Wool LiteFelt Long Teardrop Fedora Hat is a gorgeous addition to your hat

(2)
$144.50

…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 downturned brim characterize this elegant fedora hat. Finished with a Japanese grosgrain hat band, small Bailey side pin, fine woven sweatband and…

(1)
$164.05

…lightweight and features a stylish woven fabric hat band and DRI-LEX® absorbent sweatband. Keep dry and in total style this spring and summer no matter what the weather brings with the Bailey Oswego Outback Hat!   Approx. 3 3/4" - 3 7/8" Teardrop Crown 2 3/4" - 2 7/8" Underwelt Downturned…

$138.00
Available Colors:
  • NATURAL

…Ecuador, the Hinx Hand-Dyed Panama Straw Fedora Hat by Bailey is a stunning hat featuring a hand-dyed body with a twist teardrop crown and snap brim. The front of the teardrop crown has an additional dent blocked by hand. Trimmed with a natural rope hat band to give it a pinch of ruggedness. Made of…

$225.00
Available Colors:
  • RUST

…Panama Straw Fedora Hat by Bailey is a distinctive new panama hat style for the season. Alix was handwoven in Ecuador then blocked and finished in the USA by expert artisans and craftsmen. Its singularly patterned weave is beautifully complemented with a tall teardrop telescope crown and flat…

$250.00
Available Colors:
  • BLACK
  • NATURAL
  • TAN

…is a braided leather cord stitched to a horsehair braid. Part of Bailey's spring/summer straw hat line, the finishing touch is the black-dipped nail gently tucked behind the layered hat band.   Approx. 3 7/8" Teardrop Crown 2 7/8" Flat Brim   Made of: 100% Seagrass Straw …

$75.00
Available Colors:
  • NATURAL

…Gambler Hat is then treated with a 'hand-cooked' shellac for the heritage stiffened touch. No detail has been overlooked on the Bailey 1922 Lang Elite Wool Felt Gambler Hat.   Approx. 4 1/4" Teardrop Crown 3" Snap Brim   Made of: 100% Wool Felt   Made in the USA Bailey

$187.00
Available Colors:
  • BLACK
  • DENIMBLUE
  • ARMYGREEN

  Bailey's Piston Wool Felt Aussie Hat is a staple for any hat aficionado's closet. A classic wide-brim aussie hat silhouette with a teardrop crown, this hat is completely crushable/packable. The Piston is designed with a vegan leather bolo cord with metal tips. Fully lined in cotton, this hat

$68.00
Available Colors:
  • TAN

…packable, Derian is finished with a pattern woven hat band and Bailey side pin. Inside, an absorbent dri-lex® sweatband helps absorb sweat while the hat remains unlined for maximum breathability.    Approx. 3 3/4" Teardrop Crown - Front 4" Teardrop Crown - Back 3" Curved Brim    …

(2)
$135.00

…USA   With the Racer Panama Straw Fedora Hat by Bailey you get both comfort and style. This is a custom panama handcrafted in Ecuador with a woven crochet teardrop crown and brisa snap brim. Finishing touches are the Japanese grosgrain ribbon hat band and finely woven sweatband. The Racer…

$225.00
Available Colors:
  • NATURAL

…Tessier Panama Straw Fedora Hat by Bailey will add distinctive style to your look this spring and summer! Like all genuine panama hats, the Tessier's body was artfully handwoven in Ecuador then blocked and finished in the USA by master craftsmen. The resulting hat is lightweight, supple and…

(2)
$220.00

…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" Downturned…

(1)
$220.00
Available Colors:
  • NATURAL

…Fedora Hat is from Bailey is part of their Superior Fur Felt collection. Features a Japanese grosgrain ribbon hat band with an origami half bow. This is finished with a vintage flooring nail. This is a Bailey favorite, full of elegance and comfort.     Approx. 4" Long Teardrop Crown 3"…

$361.25
Available Colors:
  • SLATE
  • ARMYGREEN
  • COPPER

…Introducing Bailey's Konrath Shantung LiteStraw Fedora Hat. This is a gorgeous straw fedora crafted of premium shantung straw and boasts Bailey's exclusive LiteStraw® for a lightweight, supple and water resistant finish. You can't go wrong with this piece.   Approx. 4" Teardrop Crown 2…

$180.00
Available Colors:
  • NATURAL

…and Bailey's famous LiteStraw® finish, this hat not only protects you from harmful sun rays, it is also lightweight, flexible and water repellent. Features a colorblocked double braided leather cord hat band and leather crosspiece. For the discerning hat lover.   Approx. 4 1/2" Teardrop

$195.00
Available Colors:
  • NATURAL

…Part of Bailey's timeless 1922 collection, the Brooks Panama Straw Fedora Hat exemplifies enduring taste. The hat body is handwoven in Ecuador of genuine panama straw in a classic Cuenca weave pattern then blocked and finished in the USA. Simply trimmed with a two-tone grosgrain ribbon hat band, the…

$119.00

…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…

(6)
$170.00
Available Colors:
  • NATURALBLACK

…in the USA Bailey has given us a headwear piece that will suit everyone, the Adlay Raindura Straw Fedora Hat. The raindura straw blend and handwoven thermosetting yarn makes the Adlay both water resistant and shape retentive. With its snap brim and raised teardrop crown, this fedora is…

$135.00
Available Colors:
  • DARKNATURAL
  • NAVYBLUE

…Look no further than the striking Tasmin Panama Straw Fedora Hat by Bailey! All genuine panama hats, including the Tasmin, are handwoven by artisans in Ecuador; the Tasmin was then blocked and finished in the USA by expert Bailey craftsmen. The Tasmin's multi-color crocheted crown helps it stand…

(2)
$220.00
Available Colors:
  • MULTI
  • BLUE

…being a durable hat that will keep its shape for many years to come. The finishing touch is a hat band featuring two types of ribbon...Japanese grosgrain ribbon at the front and chambray ribbon at the back. What will Bailey think of next?   Approx. 3 7/8" Long Teardrop Crown 2 7/8"…

$140.00
Available Colors:
  • GREEN
  • IVORY

…the flexibility of the plush body makes the hat versatile. The brim has a slight curl and the crown is adorned with a narrow Japanese grosgrain ribbon hat band. Stand out this fall with Bailey's latest and greatest!   Approx. 4 1/2" Teardrop Crown 3 1/4" Slightly Curled Brim   …

$164.05

…for action, the Bailey 1922 Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This 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 with a…

$85.00

…ready for action, the Bailey 1922 Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This 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 with a pinched…

(8)
$85.00

…in the USA The Briar Wool LiteFelt Fedora Hat is a great basic to have in your collection of hats. Featuring a safari-inspired design, the Briar adds a few stylish updates including a teardrop crown and handsome leather hat band. Great for both men and women, the Briar adds sophisticated…

(2)
$110.50

…Fedora Hat  by Bailey! Part of their Bailey 1922 classic men's line, the new Packable Fedora is exclusively sold at the Village Hat Shop and features their premium LiteFelt® for a soft, packable and water repellent finish. The hat's design is as classic as it gets and includes a teardrop crown…

(2)
$130.00
Available Colors:
  • BLACK
  • RED
  • GRAPHITE

  Made in the USA The Bailey Wynn LiteFelt Wool 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:…

(1)
$110.50
Available Colors:

…nature, the Bailey 1922 Spencer Toyo LiteStraw Fedora Hat keeps the rain out and style always on. This toyo design features their exclusive LiteStraw® finish for an amazingly comfortable feel in addition to water repellency. With Bailey's LiteStraw® finish your perception of straw hats and just how…

(3)
$125.00
Available Colors:
  • NATURAL

…Toyo Straw Blend Trilby Fedora Hat by Bailey. The multi-colored braid adds dimension while the colorblocked grosgrain ribbon hat band adds contrast and interest. These finer details come together to a create a hat with effortless charm.   Approx. 3 3/4" Teardrop Crown 2 1/8" Snap Brim …

$80.00
Available Colors:
  • NATURAL

Village Hat Shop Sitemap

Call Us

USA: 1-888-VHS-HATS (1-888-847-4287)
INT'L: +1 619-906-4440 Se habla español

Email Newsletter

Shop for Hats at VillageHatShop.com | Privacy Policy | Website Accessibility | Site Map
Copyright © 1999-2020 Village Hat Shop: The #1 Source for Hats Online
*ALL SPECIAL OFFERS AND DISCOUNTS
Excludes wholesale/B2B, Certain Brand Restrictions, Special Orders or Where Otherwise Noted.

CONTACT US

We are happy to help!

1 (888) 847-4287

Mon-Sun 8am-4:00pm
Pacific Time
Se habla espanol

Customer Service | Privacy | Returns/Exchanges

Copyright © 1999-2020 Village Hat Shop
*ALL SPECIAL OFFERS AND DISCOUNTS valid for USA Ground only.
Excludes wholesale/B2B, Certain Brand Restrictions, Special Orders or Where Otherwise Noted.