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Bailey Hats & Caps
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! 
Price: $45.00
Telescope Crown Pork Pie Style Hat Made for DelMonico Hatter. Wool felt hat- Brim is 1 7/8" and can either be snapped down in the front or worn turned-up in the front.
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Price: $83.00
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 two colors, Natural and Putty. The hat h
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Price: $80.00
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: $78.00
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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Price: $53.00
Bailey Drake is a handsome Litestraw(R) hat with a center dent crown and a 2" brim that is worn snapped-down at the front. The band on this hat is two-toned and has a matching binding on th
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Price: $45.00
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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Price: $55.00
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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Price: $55.00
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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Price: $53.00
Bailey Axelrod is a packable hat made from a ribbon braid material. The hat has a teardrop crown and a stingy 1 3/8" brim worn snapped down in the front and up in the back. A lightweight cru
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Price: $55.00
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: $53.00
A popular member of the Bailey Casual Straw Hat Collection; the Bailey Salem is a soft, flexible braid hat available in three colors. Bailey Salem has a center-dent crown and a 2 1/8" brim ...
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Price: $53.00
Bailey Ryden is a braid hat with a 2" brim that is worn snapped-down in the front. Ryden has a center dent crown. The braid hat band is two colors with a tonal match to the body of the hat
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Price: $43.00
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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Price: $50.00
Bailey Merrick is a straw woven Derby included in the Bailey Heritage collection. Fashion-forward Derby shape. 2 1/8" roll brim. Available in Black.
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Price: $50.00
Available in Black and White; the Bailey Kingston is a member of the Bailey Heritage Straw Hat Collection. The Kingston is a straw block in the Godfather shape. The brim is 2 7/8" wide wit
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Price: $82.50
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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Price: $82.50
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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Price: $90.00
Bailey Noclin Leather 8/4 Style Cap included in the Bailey Casual Collection. Genuine leather with a full satin lining.
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Price: $70.00
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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Price: $35.00
Bailey Koen Ascot Cap is included in the Bailey Casual Collection. Ascot cap is a structured, firm shape that has been popular with our customers for many years. Made from 100% Wool and trimmed
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Sale Price: $64.50 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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Price: $150.00
Bailey Stanza, a Genuine Fur Felt Classic Fedora included in the Bailey Heritage Collection. The Bailey Stanza has a 2 1/2" brim and a center-dent crown. The hat is fully lined, has an int
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Price: $87.50
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: $57.50 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: $49.95 Price:
Bailey Briar is a Litefelt(R) hat with a 2" 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: $57.50 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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Price: $50.00
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: $168.00
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: $57.50 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: $57.50 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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Price: $55.00
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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Price: $49.95
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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Price: $67.00
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: $42.50 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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Price: $60.00
The Bailey Pieter Hat with Earlaps is back for a second season with the Bailey Wind River Autumn/Winter collection. The Pieter is made from 100% wool Litefelt(R), making it packable, water resist
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Price: $88.00
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: $85.00
Bailey Trenton is a Genuine Panama Hat hand-woven in Ecuador and finished in the USA. Trenton is included in the Bailey Casual Straw Hat Collection. The Trenton has a very interesting two-tone ...
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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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Price: $75.00
Bailey Collins is a Litestraw(R) shantung straw hat with a smart telescope crown and a narrow 1 7/8" brim. The hat band is black grosgrain, feather is removable. Bailey Collins has a wicki
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Price: $83.00
Bailey Maxwell contemporary, trendy, smart. New in the Bailey Contemporary Collection for Spring/Summer. The crown is an aero pinch which is a forward looking pinch front. Brim width is 1 1/2&
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Price: $55.00
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
New from Bailey for Spring/Summer; the Newbury is a braid hat with a center dent crown and a contour brim. The contour brim is pre-snapped and is worn turned-down in the front and up in the back
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Price: $60.00
Bailey Rielly is a flexible fit, packable braid hat that is a new member of the Bailey Contemporary Collection for Spring/Summer. Rielly has a teardrop crown and a pre-snapped contour brim that ...
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Price: $85.00
Bailey Grammy is a member of the Bailey Spring/Summer Contemporary Collection. Bailey Grammy has a new style telescope crown that is tapered. Brim is 1 1/2" stingy style worn turned-up all
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Price: $30.00
Bailey Jeffrey is included in the Bailey Windriver(R) Collection. Jeffrey is a comfortable low-crown hat. The crown of the cap is Natural and the peak is in a complementary color. Colors avai
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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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Price: $45.00
Rhett is included in the Bailey Contemporary Collection for Spring/Summer 2009. Rhett has a 1 5/8" brim that is pre-snapped to turn down in the front and up in the back. Material is a quay
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Price: $62.00
Bailey Plateau is a Litestraw(R) hat included in the Bailey Windriver(R) Collection of casual and outdoors hats. Bailey Litestraw(R) hats are water repellent and comfortable to wear regardless ...
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Price: $38.00
Bailey Bowman is a water repellent hat with a center dent crown and a 1 3/4" brim that is pre-snapped down in the front and up in the back. Hat has a leather hat band. Included in the Baile
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Price: $38.00
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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