Bailey Hats

33 products

    Add A-list style to your attire with hats by the all-American brand Bailey. Made for the fashionable men of the “New West”, Bailey of Hollywood hats will make you look fashionable and famous. Like the Californian businessmen, movie stars, and more of the 1920s, you will be a trendsetter in no time! 

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    What Are Bailey Hats?

    Bailey is an all-American brand that originated in Los Angeles, California in 1922 and was founded by George S. Bailey. Bailey wanted to establish a brand that catered to the fashionable men of the West Coast, and since Los Angeles was booming at that time, he knew that would be the best market.

    In the 1920s, Los Angeles's growth was well underway due to the wide range of farms, oil fields, mines, and even movies. Bailey wanted to address the needs of “New West” or California men by introducing them to the “best hat possible”. Soon, celebrities such as Gary Cooper and Cary Grant were seen wearing the Bailey Hat – this cemented Bailey’s name as being Hollywood’s best milliner. 

    As more celebrities wore the Bailey, the public wanted to look like these personalities, as well. He then built the Bailey of Hollywood store, where people could buy the same Bailey hats that celebrities wore. Everyone, from newsboys to derbies, would wear a Bailey hat. Fast-forward by 100 years and Bailey hats are still fashionable to this day!

    Why Is the Bailey Hat the “Hollywood Hat”?

    When George S. Bailey founded Bailey in 1922, his hats were a hit among Hollywood men. He was able to build a reputation of being one of the best hat designers in Los Angeles – and he maintains that reputation to this day. More than a century after Bailey was founded, the company still creates well-crafted hats that are worn by celebrities such as Bruno Mars, Ne-Yo, Townshend of The Who, and more.

    What Does the Bailey Hat Look Like?

    The Bailey hat is a men’s dress hat that features a short brim and a ribbon that wraps around the whole crown. Bailey dress hats come in a wide range of designs such as fedora hats, boater hats, and gambler hats, among others. 

    You’ll be able to tell if you're wearing a Bailey from its craftsmanship. Bailey hats are crafted from premium materials such as Panama straw, fur felt, wool, and wool felt. One of Bailey’s distinct features is the use of their patented LiteFelt finish, which adds a waterproof layer to wool felt headwear. 

    The Bailey also boasts a grosgrain hatband that’s nailed, not glued, onto the hat. This ensures that the hatband stays on the Bailey hat. The grosgrain ribbon is also laser-etched with a subtle Bailey logo.

    Why Wear a Bailey Hat?

    Bailey is known for not only being fashionable but also being incredibly durable. When you buy a Bailey of Hollywood hat, you’ll be able to wear the best hats and benefit from the best craftsmanship.

      • Elite Finish. These are felt hats that feature a distinct stiff structure that's the result of sanding and hand-finishing. Hats that have the Elite Finish include the Colver.
      • LiteFelt. Bailey hats boast the LiteFelt finish. This finish turns a wool felt hat into a water-repellant hat. An example of a Bailey that features the LiteFelt finish is the Blixen.
      • LiteStraw. LiteStraw turns the hard straw hat into a soft hat that can be worn comfortably all day. Buy the Braylon or the Outen if you want a straw hat that won’t make you sweat. 
      • Raindura. Straw hats can now be waterproof thanks to Bailey’s Raindura yarn. These hats are treated with a water-repellent coating, creating a straw hat that retains its shape at all times. 
    • Polished Wool Felt. You can’t find felt that’s as sheen as Bailey’s. Bailey’s felt hats boast a shiny surface – you can’t even tell that it’s actually felt! 

    Bailey Hat Styles

    From straw hats that make you feel like you’re in the tropics to pork pie hats that’ll make you feel like you’re in Breaking Bad, Bailey designs a wide range of headwear for the fashion-forward man. When you wear a Bailey, you will look unmistakably sleek – like the Hollywood men that George S. Bailey designed the first Baileys for!

      • Straw Hats. Wear a genuine straw hat such as the Cuban or the Creel to your tropical getaway to Florida. Pair it with calf sandals for a slightly put-together getup.
      • Fedora Hats. A fedora hat such as the pinched-top Blixen can add a classic flair to your outfit. 
    • Pork Pie Hats. You’ll look like a Hollywood director in a classic pork pie hat like the Waits or the Tim.
    • Flat Caps. For post-war fashion that’s perfect for the 21st-century streets, wear a flat cap such as the Almas to complete your outfit. 

    Buy Bailey Hats at Dapperfam

    Dapperfam has a full collection of hats by the all-American brand Bailey. Browse our website today to find the one that makes you feel like an A-list celebrity! 

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    From our customers

    ★★★★★

    The Hat was Everything I Expected and More. Great Hat, Great fit,Great look. Great Overall Service; Delivery and Packaging on point. A pleasure doing Business with Dapper Fam.

    Mr. Adams
    California
    ★★★★★

    Really love my hat. Stylish and eye catching and exquisitely made to perfection. Fits me perfectly and fits my swag too! Now I need more colors of this brand. DapperFam properly packed the hat in a sturdy box, to prevent crushing. Here on out, I'm a DapperFam man!

    Mr. Martin
    Missouri
    ★★★★★

    Highly appreciate the hat and style , the look is outstanding and brings that flare in your appearance! Must buy if you want that dapper look and style ! Will buy more when the others arrive ! Salute to your company !

    Mr. James
    Texas
    ★★★★★

    Definitely recommend and will be buying again
    Same day shipping

    This hat was the talk of the event it matched up to a tee with my suit and shoes.

    Mr. Lofton
    Tennessee
    ★★★★★

    All around dope ostrich sneakers and the cushion your feet feel is like new money!

    Mr. White
    New Jersey