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Bailey Newsboy and Ivy Caps

Bailey of Hollywood Newsboy and Ivy Caps. Bailey has an extensive Collection of fine Newsboy, Ivy, and Military Style Caps. Our customers are fond of these caps; they have a distinctive cut characteristic of the brand.

We carry the Bailey Lord, an Ivy Style cap in both solid colors and fine Italian tweeds. Meanwhile a popular Newsboy style cap is the Bailey Galvin, also available in solid colors and Italian tweeds. The Bailey Casper Flat Cap is an ivy style flat cap with a leather visor and the Bailey Stockton is an Ivy style leather cap.

Many other styles are available as well. DelMonico Hatter, U.S. Hat Retailer of the Year has a full collection of Bailey Newsboy, Ivy and other fine cap styles.

Bailey Graham Cap
Sale Price: $38.25    Price: $45.00

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. ... Read more »
Bailey Galvin Tweed 8/4 Cap
Sale Price: $72.25    Price: $85.00

The Bailey Galvin Tweed cap is made in Italy in a Donegal Tweed pattern. This fully lined traditional 8/4 style hat has a press stud peak, enabling the crown to be worn up or down. The weave has ... Read more »
Bailey Galvin Wool Newsboy Cap
Sale Price: $68.00    Price: $80.00

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 ... Read more »
Bailey Lord Ivy Style Herringbone Cap
Sale Price: $68.00    Price: $80.00

Italian made, with a soft wool feel. This Bailey Ivy Style Cap is available in a traditional herringbone tweed. Colors are Black Herringbone and Brown Herringbone. This cap comes fully lined with ... Read more »
Bailey Lord Nailhead Tweed Cap
Sale Price: $63.75    Price: $75.00

The Bailey Lord Nailhead Tweed Cap is an Italian-made cap with a soft, wool feel. Nailhead tweed is a unique offering that combines flecks of contrasting shades of a single color to create a rich ... Read more »
Bailey Lord Wool Ivy Cap
Sale Price: $63.75    Price: $75.00

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 ... Read more »
Bailey Slater Cap
Sale Price: $45.05    Price: $60.00

The Bailey Slater Cap is a handsome ivy style flat cap with a smooth crown and paneling in the back for texture and a close, sleek fit. Made of lightweight summer weight suiting fabric and lined ... Read more »
Bailey Langham Cap
Sale Price: $96.05    Price: $113.00

The Bailey Langham is a 5 panel ivy style cap with a close fit, made of fine quality pebbled leather. A classic style in a luxurious fabric. ... Read more »
Bailey Hallam Cap
Sale Price: $96.05    Price: $113.00

The Bailey Hallam is a handsome leather flat cap with a center seam and paneled sides for a sleek close fit. Made from high quality smooth leather, this classic style cap will be a cool weather f ... Read more »
Bailey Ormond Cap
Sale Price: $46.75    Price: $55.00

The Bailey Ormond is an attractive and versatile flat cap with paneled construction and a comfortable fit. Herringbone or plaid, this subtle cap is a sophisticated addition to any outfit. ... Read more »
Bailey Endell Cap
Sale Price: $53.55    Price: $63.00

The Bailey Endell is a fitted newsboy cap with a sleeker profile and classic paneled construction, topped with a button at the crown. The peak is leather, and the wool blend fabric is soft and wa ... Read more »
Bailey Lazar Cap
Sale Price: $68.00    Price: $80.00

The Bailey Lazar is a high quality 5 panel ivy style cap with a sleek profile and comfortable fit. Made from fine aged suede, this cap can be dressed up or down and always look good. ... Read more »
Bailey Edvin Cap
Sale Price: $46.75    Price: $55.00

The Bailey Edvin Cap is an ivy style flat cap with unique horizontal paneling for a modern look. The fabric is a summery linen ideal for warmer weather, and the sleek smooth black will go perfect ... Read more »
Bailey Turlock Cap
Sale Price: $51.00    Price: $60.00

The Bailey Turlock Cap is a clever ivy style flat cap in a traditional style that has recently come back into fashion in a major way. This version, made from summer weight fabric, is printed with ... Read more »
Bailey Dormer Cap
Sale Price: $68.00    Price: $80.00

The Bailey Dormer Cap is a simple, classic ivy style cap. Made from lightweight summer fabric, this cap is a great timeless look that goes with everything, taking it from dressed up to dressed do ... Read more »
Bailey Billop Cap
Sale Price: $46.75    Price: $55.00

The Bailey Billop Cap is a contoured 5 panel cap made from a summer weight suiting fabric for a smart, sophisticated look. Light enough to dress up your warmest days, this cap has a subtle glen p ... Read more »
Bailey Hemden Newsboy Cap
Sale Price: $46.75    Price: $55.00

The Bailey Hemden Newsboy Cap is a crisp, clean summer cap made from soft 100% cotton in the traditional newsboy paneled crown style. A slimmer fit and a carefully tailored silhouette give it a m ... Read more »
Bailey Jared Cap
Sale Price: $46.75    Price: $55.00

The Bailey Jared Cap is a classic flat cap with a smooth profile and sewn front peak to retain structure. Made from a summer weight cotton blend fabric, this cap is pre-washed for a comfortably f ... Read more »
Bailey Mogen Cap
Sale Price: $51.00    Price: $60.00

The Bailey Mogen Cap is a sleek, contoured cap with clever paneling to allow the closest most comfortable fit. 100% linen is patterned with subtle pinstripes and pre-faded for an easy casual look ... Read more »
Bailey Saynt Cap
Sale Price: $55.25    Price: $65.00

The Bailey Saynt Cap is a mix of traditional style and modern design; a 100% cotton summer weight cap in a classic ivy style with a flat crown and sleek silhouette, outfitted in a bold and fun fl ... Read more »
Bailey Rand Cap
Sale Price: $63.75    Price: $75.00

The Bailey Rand Cap is a traditional ivy cap in a luxurious wool blend. This cap comes in a selection of beautiful jewel tones which give a nice pop of color to your autumn wardrobe! The brushed ... Read more »
Bailey Casper Flat Cap w/Leather Visor
Sale Price: $59.50    Price: $70.00

The Bailey Casper Flat Cap w/Leather Visor is a sharp looking cap in the traditional flat cap style with smooth lines and a high quality rich leather peak for a touch of something special. The su ... Read more »
Bailey Cole Wool/Cashmere Ivy Cap
Sale Price: $80.75    Price: $95.00

The Bailey Cole Wool/Cashmere Ivy Cap is a beautiful Italian-made ivy style cap with classic lines and a soft, touchable wool/cashmere blend. The luxurious warm fabric is lined inside with smooth ... Read more »
Bailey Stockton Leather Ivy Cap
Sale Price: $89.25    Price: $105.00

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. ... Read more »
Bailey Shupp II Ascot Cap
Sale Price: $51.00    Price: $60.00

The Bailey Shupp II Ascot Cap is an updated version of an old classic. The fine wool ascot cap is blocked to shape and smoothly finished. The seamless style is accented with a small ventilated gr ... Read more »
Bailey Lord Plaid Ivy Cap
Sale Price: $63.75    Price: $75.00

The Bailey Lord Plaid Ivy Cap, part of the Bailey Italian Collection, is a traditional style ivy cap with a flat crown, snap front peak and sleek smooth lines. This version comes in a soft wool b ... Read more »
Bailey Galvin Herringbone Newsboy Cap
Sale Price: $72.25    Price: $85.00

The Bailey Galvin Herringbone Newsboy Cap is a traditional newsboy style cap with a paneled crown and button top, and is a staple of Bailey's Italian collection. This version is made from 100% wo ... Read more »
Bailey Galvin Plaid Newsboy Cap
Sale Price: $72.25    Price: $85.00

The Bailey Galvin Plaid Newsboy Cap is a traditional newsboy style cap with a paneled crown and button top, and is a staple of Bailey's Italian collection. This version is made from a soft wool b ... Read more »
Bailey Galvin Stripe Herringbone Cap
Sale Price: $68.00    Price: $80.00

The Bailey Galvin Stripe Herringbone Cap is a 100% wool newsboy cap with a unique blend of colors to form a beautifully rich mixed tweed in a herringbone stripe pattern. The paneled crown has a c ... Read more »
Bailey Galvin Windowpane Plaid Cap
Sale Price: $68.00    Price: $80.00

The Bailey Galvin Windowpane Plaid Cap is a handsome 100% wool newsboy style cap with classic paneling and a button crown. The pattern has an overlay of subtle color for an interesting dimensiona ... Read more »
Bailey Cove Cap
Sale Price: $51.00    Price: $60.00

The Bailey Cove Cap is a slim fit paneled newsboy style cap. In dark colors with a subtle plaid overlay, this is a handsome cap for your cold weather wardrobe. Made from a wool blend fabric, this ... Read more »
Bailey Seddon Wool Dockman Cap
Sale Price: $53.55    Price: $63.00

The Bailey Seddon Wool Dockman Cap is a handsome cap ideal for chilly days. The classic newsboy cap influence is here, with a modern smooth crown free from buttons or other details for a clean lo ... Read more »
Bailey Smit Cap
Sale Price: $53.55    Price: $63.00

The Bailey Smit Cap is a paneled ivy cap. This beautiful plaid houndstooth wool blend flat cap is fully lined with a comfort sweat band. A stylish hat to keep you warm during the cold weather sea ... Read more »
Bailey Byles Cap
Sale Price: $106.25    Price: $125.00

The Bailey Byles Cap is a paneled ivy style cap made from genuine lambskin leather. Fully lined and finished with a comfort sweatband. A stylish choice for the winter weather! ... Read more »
Bailey Rockburn Cap
Sale Price: $51.00    Price: $60.00

The Bailey Rockburn Cap is a traditional 8/4 newsboy style cap. This classic cap is made from a wool/cotton blend fabric making it comfortable in all weather. It comes in a textured micro houndst ... Read more »
Bailey Britten Cap
Sale Price: $51.00    Price: $60.00

The Bailey Britten Cap is a sleek 8/4 newsboy style cap. Made from a warm cotton, this hat is fully lined and finished with a comfort sweatband. This modern style of the classic newsboy is a wond ... Read more »
Bailey Mickey Herringbone Dockman Cap
Sale Price: $51.00    Price: $60.00

The Bailey Mickey Herringbone Dockman Cap is a traditional paneled cap with a smooth top and front peak. The wool blend fabric comes in two distinctive looks- one bold black and grey herringbone ... Read more »
Bailey Rickett Cap
Sale Price: $51.00    Price: $60.00

The Bailey Rickett Cap is an 8/4 newsboy style cap with a large scale dark plaid pattern. This wool blend cap is fully lined making it the perfect addition to any cold weather wardrobe! The inter ... Read more »
Bailey Gober Cap
Sale Price: $46.75    Price: $55.00

The Bailey Gober Cap is a tailored 6-panel newsboy cap made from a high-quality cotton blend fabric. This modern newsboy style cap is slim fit and patterned with narrow pinstripes for a sleek, ta ... Read more »
Bailey Deren Cap
Sale Price: $51.00    Price: $60.00

The Bailey Deren Cap is a quilted winter ivy cap. Made from a special brushed water resistant polyester. This hat is hand quilted and fully lined for added warmth. This hat features fold down ear ... Read more »
Bailey Gellerth Cap
Sale Price: $46.75    Price: $55.00

The Bailey Gellerth Cap is a paneled ivy flat cap made from a soft knit fabric. The paneling gives this hat a close fit and the hat has a dark melange pattern for a unique flat cap look. A warm, ... Read more »