BAILEY HOLIDAY GIFT GUIDE

GIFTS WORTH GIVING

Find a gift with lasting style in the Bailey Holiday Shop. From refined fedoras and flat caps to iconic Western cowboy hats, our curated collection brings together timeless silhouettes, premium materials, and signature Bailey craftsmanship for the holiday season.

Bailey Western: Western & Cowboy Hats

Bailey Western creates real cowboy hats rooted in generations of Western hatmaking tradition. These high-quality western hats span classic crown shapes, brim profiles, colors, and materials, including both straw and felt styles suited to changing seasons, working days, and more refined occasions. Thoughtful proportions, dependable comfort, and distinctive Western character define the assortment, with each hat reflecting the craftsmanship and authenticity that have shaped Bailey for generations.


  • color-dusky-citron
    15% off

    Renegade® Flynn

    $160.00 $136.50
    1 color
  • color-ivory
    25% off

    Fidler 7X

    $100.00 $75.00
    1 color
  • color-ivory-tan

    Colstrip 7X

    $100.00
    1 color
  • color-black
    🇺🇸

    Big Zwey

    $150.00
    1 color
  • color-ivory-brown

    Verdi Open

    $90.00
    1 color
  • color-ivory-navy
    25% off

    Arriba 20X

    $200.00 $150.00
    1 color
  • color-ivory

    Keystone Open

    $90.00
    1 color
  • color-ivory
    🇺🇸

    Reliance 10X Open

    $185.00
    1 color
  • color-black-cherry
    new colors added

    Pro 7X Open - 4.5" Brim

    $390.00
    7 colors
  • color-natural
    🇺🇸

    Legacy 100X Open

    $1,400.00
    3 colors
  • color-ivory-tan
    🇺🇸

    Ojai 7X

    $125.00
    1 color
  • color-linen
    🇺🇸

    Dillon 15X 4.25 Open

    $200.00 $150.00
    1 color
  • color-ivory
    🇺🇸

    Breken 20X 4.25 Open

    $200.00
    1 color
  • S23BGA
    25% off

    Gadsden

    $90.00 $67.50
    1 color
  • color-honey
    new

    Tecosa 2X

    $160.00
    3 colors
  • color-zinfandel
    new

    Renegade® Durango

    $140.00
    3 colors

Frequently Asked Questions about Bailey Western: Western & Cowboy Hats

How do I choose my first cowboy hat?

Start with crown shape and material. Cattleman crown is the most versatile and universally flattering shape. For material, wool felt works for cooler months and straw for summer. Get your head measured properly — fit matters more than anything else.

What's the difference between felt and straw cowboy hats?

Felt (wool or fur) is for fall through spring — it's structured, warm, and weather-resistant. Straw is for summer — lightweight, breathable, and cool. Many cowboy hat wearers own at least one of each for year-round coverage.

How should a cowboy hat fit?

It should sit comfortably on your head without squeezing, about a finger's width above your eyebrows. It shouldn't slide forward when you tilt your head down. The right size feels secure without pressure — snug but not tight.

What do the X-ratings mean on cowboy hats?

X-ratings indicate material quality — higher numbers mean better materials and tighter construction. In felt: higher X means more fur content. In straw: higher X means tighter weave. A 4X is good everyday quality; 10X+ is premium.

Can I reshape or customize a cowboy hat after buying it?

Yes — most quality cowboy hats can be reshaped with steam. Open crown hats are specifically made for this. Even pre-shaped crowns can be modified. A professional hatter can make significant changes, or you can do minor reshaping at home.