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Bailey Hats & Caps
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Bailey Trendy Hats
Bailey Contemporary Style HatsBailey of Hollywood Contemporary Style Hats. Bailey has a dynamic Collection of fine hats with a modern flair. These hats feature smaller brim widths, shaped crowns, braid material and unique trimming. DelMonico Hatter, U.S. Hat Retailer of the Year, has a full selection of Bailey Contemporary Hats to suit your style. 
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: $67.50
The Bailey Eco Tino II is a Toyo straw fedora hat with classic lines and classy style. The center dent crown is trimmed with a matching colored hat band topped off with a subtle Bailey pin. Simpl
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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: $57.50 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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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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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: $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: $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: $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: $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: $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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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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Price: $75.00
The Bailey Gauntlet Hat is a new contemporary offering from Bailey for Autumn/Winter. The Gauntlet has a pinch front center dent crown and a 2" rolled brim. The hat also has unique satin-bou
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Price: $75.00
For Autumn/Winter, Bailey has introduced the Hat on Hat, a new contemporary style. The Hat on Hat is made up of two wool felts: one Charcoal Grey and one Black. The two materials are pieced toget
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Price: $60.00
The Bailey Fairfax is a two-tone braid hat made from glazed cotton-wool. It features a rich Brown teardrop crown and contrasting Black 1 5/8" stingy brim. Available in Brown only, as shown.
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Sale Price: $49.95 Price:
The Bailey Mollien is a new contemporary two-tone braid hat from Bailey. The Mollien is made from a soft wool-blend tweed-patterned braids in contrasting colors. Brown/Lt. Brown has a Brown body ...
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Price: $60.00
Bailey Bobby is made from cotton blend braid material with an all-over plaid print. The hat has a teardrop crown and a stingy 1 3/4" brim worn snapped down in front. There is a small oval me
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Price: $65.00
Bailey Chet Wool Braid Fedora Hat - Bailey Chet is a trendy hat skillfully constructed from wool braid. Hat is Black with splashes of plaid color. Teardrop crown with a 1 5/8" brim. Comfo
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Price: $54.95
Bailey Cosgrove Fedora Hat - Bailey Cosgrove is a wool braid fedora hat with a teardrop crown and a 1 5/8" brim that can be snapped-down in the front or worn turned-up all the way around. T
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Price: $55.00
The Bailey Brigham Hat is a packable braided poly-blend fedora with a teardrop crown and directional arrow pattern that gives this hat a unique spiral effect. Soft and crushable with a woven inte
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Price: $75.00
The Bailey Bronc is a stylish offering for Autumn/Winter from the popular Wind River Collection. The Bronc is made from 100% wool that has been distressed for an artistic, worn effect. The has ha
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Price: $49.95
The Bailey Elliott is a straw braid trilby style fedora with a pinched front crown and snapped down 2" brim. This contemporary looking straw hat has a simple fabric hat band and is a light b
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Price: $63.00
The Bailey hardy is a soft Toyo straw fedora with a rounded center crease crown and 1 1/2" stingy brim. Wear it up all around or snap down in front, this modern trendy style breathes new lif
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Price: $62.50
The Bailey Harley is a fabric braid fedora in a sharp trilby shape with a short 1 3/8" snapped down brim and teardrop crown. Crushable and packable, it is a comfortable easy fit and a casual
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Price: $65.00
Bailey Hawke Fedora Hat - Bailey Hawke is a wool felt hat with a diamond crown and a 1 1/2" brim. The brim can be worn snapped-down in the front or turned-up all the way around. Hat is tr
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Sale Price: $57.50 Price:
Bailey Jamie Wool Felt Fedora- New Introduction to the Bailey line for Autumn/Winter. Jamie is a smartly-trimmed wool felt hat with a 1 1/2" stingy brim that snaps down in the front. Baile
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Price: $88.00
The Bailey Knott is an asymmetrical crowned panama straw hat with a contemporary flair. The stingy 1 3/4" brim can be worn up or snapped down in front, and the exaggerated fedora shape is a ...
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Sale Price: $59.95 Price:
The Bailey Lamar is a traditional pork pie style hat with a twist. The lightweight soft straw braid curves around the classic telescope crown while the modern stingy 1 1/2" brim can be worn ...
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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: $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: $63.95
The Bailey Clayd Fedora- The Bailey Clayd Fedora is a sculpted wool felt fedora with a unique grid texture along the telescope crown. A modern 1 1/2" stingy snap brim gives the hat extra att
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Price: $99.95
The Bailey Hornblower Pork Pie Hat- The Bailey Hornblower is a very handsome modern pork pie hat, with a classic telescope crown and 1 5/8" snap brim that can be worn up all around or snapped dow
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Price: $63.95
The Bailey Bram Fedora- The Bailey Bram is a crushable, packable plaid fedora made with 100% cotton ribbon stitched into a classic trilby fedora shape. A mix of the traditional and the modern, th
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Price: $67.95
The Bailey Manon Trilby Hat- The Bailey Manon is a truly unique trilby fedora. Classic trilby shape meets modern style with a short 1 1/2" brim that can be snapped down in front. The hat is const
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Price: $54.95
The Bailey Chron Hat- The Bailey Chron Hat is a trilby style fedora with a pre-snapped 1 3/4 inch stingy brim. This fashionable fedora has a paneled construction and alternating solid wool and he
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Price: $112.95
The Bailey Raf Fedora- The Bailey Raf Fedora is a beautiful wool/cashmere blend fedora with a pinched center crease crown and stingy 1 1/2 inch brim. This soft comfortable hat is accented with gr
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Price: $112.95
The Bailey Sweigart Porkpie Hat- The Bailey Sweigart Porkpie Hat is a telescope crown porkpie hat in luxurious wool/cashmere blend felt with a stingy 1 1/2" snap brim. This smooth soft hat featur
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Price: $175.95
The Bailey Lesher Fur Felt Porkpie Hat- The Bailey Lesher Fur Felt Porkpie Hat is a 100% genuine fur felt hat with a touchably soft velour finish. A classic telescope crown and stingy 2" snap bri
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Price: $70.00
Bailey Sergeant Wool Felt Top Hat - Bailey Sergeant is a wool felt top hat with a 5" tall crown and a 2 1/4" brim. The brim is trimmed with a grosgrain binding at the edge matching the
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Price: $60.00
Bailey Eco Tino Fedora Hat - The Bailey Tino fedora hat has been a top-seller at DelMonico Hatter; Eco Tino takes the popular Tino shape and using a eco-vegetable dye, produces the Hazelnut color
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Sale Price: $110.00 Price:
The Bailey Sawyer Panama Hat is an attractive telescope crown hat with a 2 inch pre-snap brim. Made of genuine panama straw in two-tone stripes woven in a complex Brisa weave, this handsome hat i
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Price: $67.50
The Bailey Newington Hat is a flexible Litestraw fedora made of soft paper Toyo straw. Shaped with a deep dip crown for a sleek profile and featuring a stingy modern contour brim, this fashionabl
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Price: $67.50
The Bailey Maynard Hat is a fashionable modern fedora with a diamond crown and stingy 1 1/2 inch pre-snap brim. Made of smooth Toyo straw, this hat is finished off with a wide ribbon hat band. A ...
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Price: $72.50
The Bailey Keynes Hat is a trendy modern straw hat made of smooth Sisal straw. This lightweight warm weather fedora has a classic teardrop crown and a modern very stingy 1 inch brim. This sleek b
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Price: $67.50
The Bailey Moran Hat is a sleek black bowler style hat in soft Toyo straw, perfect for summer. The classic rounded bowler crown leads to an upturned brim and the hat is finished with a black gros
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Price: $74.95
The Bailey Scout Hat is a lightweight woven Jute/Seagrass fedora with a beautiful swirled stripe pattern and breezy open weave. The classic teardrop crown meets a 2 inch casual brim for an easy f
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Price: $72.50
The Bailey Foster Hat is a light woven Jute rope hat with a classic telescope crown and stingy modern 1 1/2 inch pre-snap brim. This fashionable hat features an open weave for ventilation on hot ...
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Price: $92.50
The Bailey Pine Hat is a light wool hat with a telescope crown and 2 inch snap brim. Stylish and soft, this hat is fully crushable and packable, and can be rolled into the accompanying carry bag ...
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Price: $49.95
The Bailey Talvar Pull On Cap is a sophisticated update of the typical knit hat. Made of smooth soft cotton/silk, this stretchy cap has panels of detailed cabling and openwork for an attractive t
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Price: $65.00
The Bailey Sharmon Hat is an attractive modern telescope crown hat made of soft flexible Sisal braid. The fashionable stingy brim has a bound edge and the whole hat has a seamless simple look tha
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