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Bailey HatsBailey of Hollywood. Bailey began producing fine dress headwear in 1922, priding itself on founder George Bailey's emphasis on the importance of a professionally crafted hat. Bailey has evolved from fine dress headwear to now include Outdoor Collections (Bailey Wind River) and Contemporary Hat Styles. 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! 
Sale Price: $172.50 Price:
The Bailey Fur Felt Pork Pie Hat has a classic telescope crease in the crown. This hat has a small 1 3/8"" brim that can be snapped down or worn turned-up. The hat is fully lined and ha
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Sale Price: $99.95 Price:
Bailey Sydney is a Genuine Panama Hat hand-woven in Ecuador and finished in the USA. Sydney; included in the Bailey Causal Straw hat Collection comes in several colors. The hat has a teardrop c
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Price: $107.50
Bailey Cutler is a soft 100% Genuine Panama Hat hand-woven in Ecuador with a center-dent pinch, graduated crown and a 2 7/8" pre-snapped brim. The Cutler has a tooled leather hat band and a ...
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Price: $107.50
Bailey Brooks is a Genuine Panama Hat with a teardrop crown and a 2" downbrim. Brooks has a grosgrain hat band and an interior sweatband. This hat has a heavier body. Hand-woven in Ecuador a
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Sale Price: $58.95 Price:
Bailey Spencer is a Litestraw(R) hat included in the Bailey Casual Straw Collection. Crown on this hat is teardrop style. The 2 3/8" casual brim can be worn turned-down all the way around.
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Sale Price: $55.00 Price:
Bailey Billy has a teardrop crown and a stingy 1 3/4" brim that is snapped-down in the front. It is a soft, flexible braid hat with a matching braid hat band and an interior sweatband inclu
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Sale Price: $55.00 Price:
Bailey Mannes is a multi-colored braid straw hat with a textured hat band that goes well with the color of the hat. The low c-crown shape measures 3 3/4"; it has a pinch. Bailey Mannes has ...
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Sale Price: $119.95 Price:
The Bailey Lakewood Genuine Panama Hat is a handsome 100% genuine panama straw hat with a mixed taupe/lake color scheme that is truly unique. Woven in a Hamaca/Cuenca weave pattern for depth and ...
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Sale Price: $74.95 Price:
The Bailey Miles Hat is a classic pork pie crown hat woven from lightweight Bao straw. The weave on this hat is especially complex and beautiful, with a textured design and slight ventilation for
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Sale Price: $57.50 Price:
Bailey Johnny is a Straw Braid Porkpie Style Hat. The Johnny is flexible and packable. The brim on this hat is 1 3/8" and is worn snapped-down in the front or turned-up all the way around. C
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Price: $53.00
Monroe is included in the Bailey Casual Straw Hat Collection. Bailey Monroe is made from a soft, flexible braid that is comfortable to wear. Hat is two-toned; crown is Ivory with a collection o
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Price: $57.50
The Bailey Salem Hat is a classic braid fedora with a center dent crown and 2 inch snap brim. Flexible and soft, this hat is finished with a bright striped band for a cheerful and elegant summert
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Sale Price: $59.95 Price:
Bailey Tennessee is included in the Bailey Casual Straw Hat Collection. Hat is made from a very lightweight quay straw. Crown is pinch-front and the 1 3/4" brim is pre-snapped to be turned
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Sale Price: $81.50 Price:
Bailey Taxten is a 100% sheepskin leather cap. Taxten is Ivy Style and is constructed of individual panels. Leather is a handsome weathered Brown. There is a small Bailey pin on the left-rear ...
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Sale Price: $78.95 Price:
Bailey Stockton Leather Ivy Style Cap included in the Bailey Casual Collection. Soft rich-feeling cap finished with a full satin lining. The cap is trimmed with a Bailey Pin on the left side.
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Sale Price: $87.95 Price:
Bailey Noclin Leather 8/4 Style Cap included in the Bailey Casual Collection. Genuine leather with a full satin lining.
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Sale Price: $78.95 Price:
Bailey Cole Cashmere and Wool Blend Ivy Style Cap- 50% Cashmere and 50% Wool blend. Handsome, comfortable fitting cap with a full-cut back and a full satin lining. Trimmed with an Oval Bailey Pi
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Sale Price: $68.95 Price:
Bailey Godfather is a Wool Felt Classic Hat included in the Bailey Heritage Collection. The original name for the Godfather style hat was the Homburg. The Bailey Godfather has a 2 3/4" bri
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Sale Price: $97.95 Price:
Bailey Perry is included in the Bailey Casual Felt Hat Collection. The Perry has a 2" snap brim and a center-dent crown. Lavalee is made from Bailey Lanolux(R), which is 100% virgin wool w
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Sale Price: $95.00 Price:
Bailey Brandt has a 2 1/2" brim worn turned-down all the way around. Crown is center-dent style. Brandt is made from Bailey Lanolux(R)- 100% virgin wool with a suede finish. After the ini
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Sale Price: $73.95 Price:
The Galvin Wool 8/4 Cap is an Italian-made larger bodied cap made up of several panels sewn together. The traditional 8/4 style cap has a press stud peak, enabling the crown to be worn up or down
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Sale Price: $58.95 Price:
Bailey Briar is a Litefelt(R) hat with a 3" down brim, teardrop crown, and leather hat band. Soft and packable, with memory, Litefelt(R) hats spring back to their original shape. Bailey use
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Sale Price: $64.95 Price:
Bailey Curtis is a Litefelt(R) hat in the Casual Felt Hat Collection. The brim is 2 1/2" worn turned-down all the way-around. The crown has a low-profile and with a pinch. Bailey uses lea
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Sale Price: $69.95 Price:
Bailey Yates is a Litefelt(R) hat included in the Bailey Casual Felt Hat Collection. Bailey uses leading technology to produce Litefelt(R); a water repellent felt made of 100% wool. Soft and pa
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Price: $50.00
Bailey Packer Hat - You can roll-up this hat for packing. Bailey Packer is a Litefelt(R) hat included in the Bailey Casual Felt Hat Collection. Bailey uses leading technology to produce Litefel
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Price: $192.50
Bailey English Derby is a fur felt hat with a stingy rolled brim. The crown is derby/bowler style, fully lined and trimmed with a grosgrain hat band. This hat was a standout on the runways. Th
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Sale Price: $75.95 Price:
Bailey Silko, included in the New Bailey Contemporary Collection. Bailey Contemporary hats feature trendy styles for winter. Smaller brims are the hallmark of the collection. The Silko is a wo
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Price: $55.00
Bailey Renny, included in the New Bailey Contemporary Collection. Bailey Contemporary hats feature trendy styles for winter. Smaller brims are the hallmark of the collection. The Renny is a wo
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Sale Price: $65.00 Price:
Bailey Wynn is a Litefelt hat included in the Bailey Contemporary Collection. Litefelt hats are crushable, packable, water repellent and comfortable to wear. The Bailey Wynn has a contour brim ...
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Sale Price: $63.95 Price:
Bailey Jamison is a Litefelt hat included in the Bailey Contemporary Collection. Litefelt hats are crushable, packable, water repellent and comfortable to wear. The Bailey Jamison has a small 1
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Price: $65.00
Bailey Shylock is a Litefelt hat included in the Bailey Contemporary Collection. Litefelt hats are crushable, packable, water repellent and comfortable to wear. The Bailey Shylock has a small 1
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Sale Price: $59.95 Price:
Bailey Darron Telescope-Crown Hat - New from Bailey and Made in USA, Darron has a telescope crown and a 1 1/2" brim that can be snapped-down in the front or worn turned-up all the way-around
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Sale Price: $72.95 Price:
Bailey Jett is a special hat for that special occassion. Bailey Jett is a wool felt hat with a silk finish. The crown is pork pie style trimmed with a matching grosgrain hat band. There is a s
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Sale Price: $49.95 Price:
Bailey Dalton is a water repellent hat. Dalton has a pinch crown, a 2 5/8" brim that is worn turned-down all the way around, and a leather hat band. Included in the Bailey Windriver(R) Col
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Sale Price: $97.95 Price:
The Bailey Vega is a Trapper Hat offered in the Bailey Wind River collection for Autumn/Winter. Supple black leather and sleek black faux-fur update the traditional Trapper shape for a more conte
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Price: $63.00
The Bailey Harper is a soft, easy-to-wear Winter cap made from a Cashmere blend. The Harper has a thick chunky knit and subtle variations in the colors of the weave. The cap has a Bailey leather ...
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Price: $70.00
We have specially ordered some good-quality, wool felt green derbies for the St. Patrick's Day festivities. Whether for your lodge party, a parade gathering, or anything else, this derby will be ...
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Price: $80.00
Bailey London Derby is a contemporary Genuine Panama Hat. The hat, hand-woven in Ecuador, is finished in the USA. Bailey London Derby is a fashion-forward hat. Hat has a 1 1/2" stingy bri
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Price: $88.00
Bailey York, Genuine Panama Hat, is new for spring/summer. This panama hat is hand-woven in Ecuador and finished in the USA. Bailey York has an aero pinch crown and a 1 1/2" stingy brim. ...
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Sale Price: $55.00 Price:
Bailey Charlie is a Straw Braid Porkpie Style Hat. The Charlie is flexible and packable with a 1 3/8" brim and is worn snapped-down in the front or turned-up all the way around. Comfortable
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Price: $85.00
Bailey Oscar; aero pinch crown, 1 1/2" stingy brim, member of Spring/Summer Contemporary Collection. The aero pinch crown gives a trendy forward looking style. Material is a patterned quay
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Sale Price: $38.95 Price:
Bailey Graham is a full-shaped cap with a leather tab at the back. Color shown is Tan. Graham is in the Bailey Windriver(R) Collection; a great hat to wear in all weather conditions.
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Price: $42.00
Bailey Wade is included in the Bailey Windriver(R) Collection for Spring/Summer. Bailey Wade has a pinch crown and a 3 1/4" brim worn turned-down all the way around. Great sun protection ou
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Sale Price: $64.50 Price:
The Bailey Ice is a wool felt Top Hat included in the Bailey Heritage Collection. The Ice has a 5" Tall Crown and a 2 1/8" Roll Brim. The brim is bound on the edge with a coordinating b
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Sale Price: $69.95 Price:
The Bailey Gangster is a 100% Wool Felt Hat. The hat has a 2 1/2" brim and a center dent crown. The feather shown is removable. The hat is fully lined and has an interior sweatband. Made in ...
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Sale Price: $58.95 Price:
Bailey Tino Litefelt Hat is our Best Selling 100% Wool Felt Hat. The hat is soft, packable, and water repellent. The Tino has a 2" brim and a center dent crown. Feather is removable.
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Sale Price: $202.50 Price:
The Bailey Madison is a Classic Fur Felt Hat Handcrafted in the USA. This fully lined hat is fitted with a genuine leather sweatband and is delivered to you in a custom hat box. The center-dent c
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Sale Price: $175.00 Price:
Bailey Duke is a fur felt classic hat with a small 1 1/2" brim that is worn snapped down in the front. Bailey Duke has a center crease crown, is fully lined and has an interior leather swea
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Price: $48.00
The Bailey Kooning Plaid Cap is a stylish Contemporary offering from Bailey for Autumn/Winter. The Kooning is an Ivy Style Wool-blend cap with a short snap peak. Color is a subtle Black and Deep ...
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Sale Price: $53.00 Price:
The Bailey Parks Litefelt(R) Army Cap is a new cap for Autumn/Winter from Bailey. Popular Army Cap shape made from Bailey's signature Litefelt(R) material - packable, water repellent 100% wool. S
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Price: $63.00
For Autumn/Winter, Bailey introduces the Rawlston Litefelt(R) Army Cap. Popular Army Cap shape updated with water repellent, packable Litefelt(R) 100% Wool. The Rawlston has laser-cut detailing a
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Price: $63.00
The Bailey Coby Litefelt(R) Hat features a new telescope crown and a 2" snap brim. Made from soft, packable Litefelt(R), this hat can travel with you. The hat has a narrow grosgrain hat band
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Price: $63.00
The Bailey Warrick Litefelt(R) Hat is a new item from Bailey for Autumn/Winter. The Warrick has a teardrop crown and a contour pre-snapped brim. Made from 100% wool Litefelt(R), the Warrick is wa
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Sale Price: $37.95 Price:
The Bailey Ferris cap is a rich tweed cap. The Ferris has a contour peak sewn to the cap body for shape retention and is sewn from four individual panels. Included in the Bailey Casual collection
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Price: $63.00
Packable, water repellent, and able to snap back to its original shape, the Bailey Abner- made from Litefelt- has an aero pinch crown and a stingy 1 1/2" snap brim. The Abner also features a
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Sale Price: $69.95 Price:
Bailey New Yorker Fedora Hat- Long a mainstay in the Bailey Heritage Collection. Calls to mind classic elegance, Mad Men, and Old Hollywood style. Wool felt fedora with a 1 7/8" brim that is
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Sale Price: $82.50 Price:
The Bailey Barr Felt Hat has a center dent crown and a 2" Brim. Made of 100% Virgin Wool with a unique suede finish; lightweight, packable, and luxurious. The hat has a matching grosgrain ha
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Sale Price: $62.00 Price:
The Bailey Fairbanks is an outdoorsy shape in water-resistant, 100% Wool Felt. Large sizes rest easy- this hat has the feature of coming in XXXL! (Comes in smaller sizes, too, of course.) Soft, p
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Sale Price: $67.95 Price:
The Litefelt Fedora is a 100% Wool Felt Water Repellent Hat. Litefelt hats are crushable and always spring back to their original shape. Fedora has a pinch crown and a 2 7/8" brim. Made in U
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Price: $54.95
The Bailey Lord Classic Cap is Italian made with a soft wool feel. A press stud peak enables the crown to be worn up or to snap down into place, according to your liking. This hat comes fully lin
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