A smiling man wearing a black shirt and a straw cowboy hat
An angle view of a Trail Boss Straw Cowboy Hat
A front view of a Trail Boss Straw Cowboy Hat
A man in gray shirt, looking slightly to the side, and wearing his Trail Boss Cowboy Hat
A side view of a Trail Boss Straw Cowboy Hat
A back view of a Trail Boss Straw Cowboy Hat
A smiling man wearing a black shirt and a straw cowboy hat
An angle view of a Trail Boss Straw Cowboy Hat
A front view of a Trail Boss Straw Cowboy Hat
A man in gray shirt, looking slightly to the side, and wearing his Trail Boss Cowboy Hat
A side view of a Trail Boss Straw Cowboy Hat
A back view of a Trail Boss Straw Cowboy Hat
4.8
Rated 4.8 out of 5 stars
4.8 Stars (31 Reviews)

Trail Boss | Mens Open Crown Bangora Straw Cowboy Hat

$53.00 $77.00 Sale Save
Color Bicolor
PICK A SIZE
Click Here for Sizing

100% Happiness Exchange Policy

Returns within 90 days receive a full refund.

SHIPS IN 1 DAY | GUARANTEED

Fast Shipping, like a Cheetah

Looking for a stylish and sturdy straw hat that will keep you cool all summer long? Look no further than the Trail Boss - Straw Cowboy Hat! This bicolor hat features a medium brown band and sewn in sweatband for a comfortable fit. A sewn-in elastic sweatband means you'll have all day comfort but we also include 2 free adhesive reducers to make sure it's a perfect fit (a $10 value).

  • Brim Measures 4" Crown Measures 5 1/2"
  • 1/4" Width Cloth Hatband
  • Lightweight Firm Straw Cowboy Hat
  • Open Cowboy Crown with Wide Brim
  • Sewn-in elastic sweatband creates a snug and secure fit
  • Often ordered one size bigger and adjusted down using size reducers (included)
  • Package includes two (free) adhesive size reducers to achieve a perfect fit, a $10 value

Yes, we do mean unlimited. At American Hat Makers we want to make sure you love your hat, because it’s going to last a lifetime.

So if your hat is the wrong size or you just don’t love the style for any reason, then you can send it back for an exchange free of charge. That’s free shipping back to us and free shipping back to you.

Not sure about your fit? Call us! A real person and expert hat fitter will be on the other side of the line to answer any questions about fit, exchanges, style or returns 831-722-3324. Or click here: Hat Sizes for our full guide.

*Please note that any Sale items are final sale and not eligible for unlimited free exchanges.*

For full details and FAQs, click here to learn more or process an exchange.

American Hat Makers headwear is built to last a lifetime, so we want you to take your time falling in love with your new favorite hat.

Take 90-days to make sure your hat is the perfect fit and the perfect style. If for whatever reason you don’t love your hat and want to return it, we make it as easy as possible.

Just pay a small shipping and restocking fee of $9.83 (which will be automatically deducted from your refund amount), send back your hat, and you’re good to go.

Not sure about your fit? Call us! A real person and expert hat fitter will be on the other side of the line to answer any questions about fit, exchanges, style or returns 831-722-3324.

For full details and FAQs, click here to learn more or process a return.

We are American Hat Makers

50 Year Craftsman Guarantee

All our hats come with a lifetime warranty. What this means is that even if you bought a hat 50 years ago and it starts unraveling, we'll fix it or replace it, free of charge.

Family Business

Second generation USA owned and operated. This company started as a family business, and has continued to stay a family business even through today

HANDCRAFTED SINCE 1972

We work hard every day to continue to be the best hat makers in America. Though we are steeped in tradition, we embrace modern practices to deliver hats of the highest quality.

Our Hats Have Been Seen On

  • Top Grade Materials - Manufactured to the highest standard, our materials are put through rigorous testing to ensure their quality and then expertly crafted into one of our timeless designs. Our leather is supple, our felt is durable, and our straw tightly woven. 
  • Hats That Hold Their Shape - All American Hat Makers hats are guaranteed to hold their shape, and will not stretch or shrink with everyday wear. This mens leather cowboy hat can be restored even if it gets warped. Purchasing our lifetime refurbishment at checkout will guarantee that if your hat is accidentally damaged you can send it back to us for a painless and timely repair.
  • They Fit! - Our hats fit! It sounds simple enough but with so many shapes and sizes of heads out there it can be a challenge. To overcome this obstacle we’ve designed several fit adjustment systems, all of which remain hidden behind the sweatband to keep your hat looking sharp from all angles. Check out more here.

Every one of our hats come with a 50 year guarantee. That means that if your hat fails in any way to meet your standards due to our craftsmanship then we’ll repair or replace your hat free of charge. So if your hat starts unraveling in 50 years, we’ll take it back and make it right.

Call us anytime! We don’t want to hide behind our website. We’re real people with a deep love and understanding for all of our hats; so any questions you have we’ll be ready to answer them. Need help picking out a hat? We can do that too! Not only can we help you with any questions or concerns you’re having, we can also help you find the perfect hat for your face shape and lifestyle.

We’re available 9am-5pm PST - give us a call at 831-722-3324.

We dislike returns just as much as the next person, so we’ve vowed to ALWAYS make returns and exchanges painless. If you don’t like your hat, if it doesn’t fit, or you want a different one - we’ll help you. Read our full return and exchange policy here.

Click here to make a return.

Our Hats Have Been Seen In

Hat Sizing Chart

Standard Sizing Chart

Centimeters

Inches

Our Size Your Head Measurement Standard Hat Size
OS One Size Fits Most One Size Fits Most -
XS 20" - 20 7⁄8" 52cm - 53cm 6 1⁄2
SM 21" - 21 7⁄8" 54cm - 55cm 6 7⁄8
MD 22" - 22 3⁄4" 56cm - 57cm 7 1/8
LG 22 7⁄8" - 23 1⁄2" 58cm - 59cm 7 3⁄8
XL 23 5⁄8" - 24 1⁄4" 60cm - 61cm 7 5⁄8
2X 24 3⁄8" - 24 7⁄8" 62cm - 63cm 7 7⁄8
3X 25" - 25 5⁄8" 64cm - 65cm 8 1⁄8

How to Measure Your Head

  1. Grab a soft measuring tape or a piece of string (like twine or a shoelace) and a ruler or measuring tool
  2. Wrap a soft tape or string around your head to measure about 1/4 to 1/2 inch above your ear and about 3/4 to an 1" inch above your brow line (see image)
    • Mark the tape or your string, where it intersects, with your finger.
  3. Record your measurement in inches or centimeters (centimeters is often more accurate)
    • If you're using a string, run it along side the ruler as many times as necessary to get a complete measurement
  4. MEASURE AGAIN!
    • Always measure more than once until you get the same number twice
  5. Find your size in the chart for the perfect fit

Flexfit Sizing Chart

Centimeters

Inches

Our Size Your Head Measurement
S/M 22 1/8" - 22 3/4" 55cm - 57cm
L/XL 22 7/8" - 23 5/8" 58cm - 60cm

Reviews

4.8
Rated 4.8 out of 5 stars
Based on 31 reviews
Total 5 star reviews: 27 Total 4 star reviews: 3 Total 3 star reviews: 0 Total 2 star reviews: 1 Total 1 star reviews: 0
97%would recommend this product
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31 reviews
  • .A
    .Michael A N.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    5 hours ago
    The perfect hat were really hot days.

    When it gets hot enough to wonder if, I'm still living in the Pacific Northwest or in Texas, this will be the hat, that I will be wearing. I now have a hat for every season.

    AH Profile picture for American Hat Makers
    American Hat Makers
    16 seconds ago

    Thank you so much for taking the time to share your positive shopping experience with us!
    We're thrilled to hear that you're so happy with the Trail Boss Hat. Your satisfaction is our
    top priority! Enjoy!

  • WC Profile picture for Woody C.google logo
    Woody C.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    1 week ago
    Great Hat

    I love the style and the unique sweat band. It seems to grip your head keeping the hat from falling off as you bend over while you are working.

    AH Profile picture for American Hat Makers
    American Hat Makers
    1 week ago

    Your review made our day, and the photo you shared is the icing on the cake! We're thrilled to
    have been a part of your positive experience, and we hope to create many more memories
    together. Enjoy!

  • DH Profile picture for Dominique H.
    Dominique H.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    6 months ago
    Great!

    Very high quality! Great fit! Fabulous look!

    AH Profile picture for American Hat Makers
    American Hat Makers
    6 months ago

    We're thrilled to hear that you found our product to be of very high quality, with a great fit and a fabulous look! Your positive feedback is truly appreciated. If you have any more comments or suggestions, feel free to share. We're here to make your experience even better!

  • R
    Rickie
    I recommend this product
    Rated 5 out of 5 stars
    4 months ago
    5 Stars

    Been on vacation. Haven’t opened it yet. I’m sure it’ll be fine. Everything that I’ve got from American hat makers has been chop shell I’m sure this is the same. Very good quality.

  • BL
    Brian L.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    6 months ago
    Great quality

    Love it!

  • DD
    Drew D.
    Verified Buyer
    I do not recommend this product
    Rated 2 out of 5 stars
    9 months ago
    Drew’s review

    The Trail Boss hat was not what I expected. I don’t like the sweat band, but I will deal with it.

    AH Profile picture for American Hat Makers
    American Hat Makers
    9 months ago

    Thank you for your review. We do apologize if the Trail Boss didn't meet your expectations. If there's anything that we can help you to make your experience better, please contact us via email at info@americanhatmakers.com or via phone call 1 (831) 722-3324. Thank you for supporting American Hat Makers.

  • E
    Elisabeth
    I recommend this product
    Rated 5 out of 5 stars
    9 months ago
    5 Stars

    Hat super light and can be fitted to my small head. Have never hat that fit until American Hat Makers

  • BK
    Barbara K.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    10 months ago
    Straw hat

    Love the wide brim!

  • AH
    Alan H.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    10 months ago
    Another great hat

    The taller crown is wonderful for a bigger head size. Very comfortable, glad I bought it. Highly recommended.

  • KE
    Kidd E.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    10 months ago
    Straw hat

    Good hat! Perfect fit with your sizing chart. The updates you gave me with shipping etc. We’re spot on I’ll definitely use y’all again.

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