A blog by "America’s Best Dressed Real Man". Fashion tips, answers to your questions, and all things men’s style
Tuesday January 31st 2012



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Classic Headwear featuring Stetson & TSB Team


It’s always great to have the team together – especially for showroom visits.

Last month when we visited the Stetson office we were missing Westley, but Karyn – soon to be host of The Style Blogger for Her - filled in nicely.

We each selected our favorite hat from their current season’s well-rounded collection and styled it in our own way.

Townsend, PR/Media Assistant – Wool Herringbone Cap

What I love about Townsend’s style is that it’s always very classic. It’s not over-thought, it’s natural. It’s preppy without the overdone in-your-face “modern twist”. The way preppy was meant to be. It’s him. He’s been dressing in cords, oxfords and peacoats for years and will continue to do so forever.

Naturally, he went with an Ivy Cap in a classic menswear fabric.

A wool herringbone driving cap in a neutral color (like grey, navy, green, black, brown) is the type of hat you fall in love with. You find it surprisingly versatile. It goes with everything. Then it breaks-in and gets very comfortable. It’s warm. Cozy, you might say. Then you find yourself missing it. And suddenly applying hair product is a pain. It’s a relationship now.

And that’s why men have old, classic hats.

Wide herringbone wool cap by Stetson. Crewneck sweater by Rugby. Peacoat and corduroys by JCrew (I had the buttons changed). Oxford shirt and sunglasses by Polo Ralph Lauren. Cap toe shoes by Aldo. 

Chris, Head of Video Production – “Boss of the Plain” Cowboy

When in Rome, do as the Romans do.

“This may not be a typical outfit for me, but I like to dress appropriately for all occasions; a nice dinner, a party or even a rodeo. I’m working on a documentary about bull riding and thought I should make the effort.

This boss of the plain hat looks so authentic. The detailing gives it a worn feel so I won’t look like I just ripped the tag off my new hat when I’m around real cowboys.

I tried to mix in my own personal style so it’s more natural and not too costumy. Ralph Lauren makes great classic, rustic American pieces so it’s easy to make his clothes look a little country.”

“Boss of the Plains” cowboy hat by Stetson. Denim jacket and western shirt by Ralph Lauren Denim & Supply. Cords by Rugby. Boots by John Varvatos

Dan, Founder/Author – Felt Fedora

When a friend of mine told her grandfather to pack his suit, he packed a jacket, trousers, shirt, tie, shoes, socks, braces, and a hat.

Believe it or not, there was a time, not very long ago, when a man wouldn’t step outside his house without a hat on. And it wasn’t a baseball cap or a beanie. It was a fedora (or a similar shape).

Men rarely wear brimmed hats anymore, it’s a shame that things have swung so far the other way. The good news is, wearing a classic felt fedora, the same hat that men have been “pulling off” day-in and day-out for years, is now considered a style statement by many.

A classic felt fedora can be dressed up or down and is awesome for the rain. One of the things that guys forget when they buy cheap headwear is that hats should be able to protect your head from the elements. This one (and my “grandma” featured here) are my rain hats. They take a beating keeping my head warm, face dry and hair in place. But because they’re well-made hats blocked in quality fabrics, even after a tough storm they dry quickly and bounce back into shape .

Classic fedora hat by Stetson. Tench by Brooks Brothers Black Fleece (sz 2, cropped). Shirt and trousers by Michael Andrews Bespoke. Tie by Smart Turnout. Shoes by Barker Black. 

Alex, Head of Photography – Fine Felt Fedora

“The Stratoliner is a Stetson classic, one of the oldest styles.

Just like Chris’ Boss of the Plain, the Stratoliner was originally created to be a working man’s hat. A nice wide brim and a domed top (original models had a domed top, but now it’s sold “pre-crushed”) kept the wearer cool and shaded in the sun, and dry in the rain.

To pay homage to the hat’s original intent I paired it with dark jeans, a classic wool workmans shirt and some broken-in leather boots.”

“Stratoliner” fine fur fedora hat by Stetson. Blue oxford by Gap. Plaid workshirt/jacket no tags (thrifted). Denim by J. Crew. Desert boots by Clarks (resoled) with red laces from J. Crew.

Westley, Photography Assistant – Donegal Tweed Cap

“Gotta love a hat that goes with everything – including this full-shearling-lined leather bomber jacket. My best vintage find of 2011 by far.”

“Madison” donegal tweed cap by Stetson. Scarf by  JCrew. Shirt and tie by Gant. Jacket Vintage Schott. Cargos by Uniqlo. Boots by Sebago. Bracelet handmade in the Philippines. Shades by Carrera.



Thanks, as always, for reading.

Plenty more from the team to come.

Yours in style,



Leave a Comment



  • More Than Stats says:


  • bb says:

    Anybody have hat suggestions for a smaller head?

    Same deal with sunglasses, for that matter…

  • Jeffrey says:

    Westley – that bomber is fantastic! I can never find good vintage – when I do it never fits. What’s the secret to good vintage finds?

  • Kristopher says:

    @Townsend I’m looking to swap the black buttons on a peacoat for some brass ones as well. I’m just wondering where you were able to find them or if you have any advice on the best places to find a similar style of buttons (I’m thinking an army surplus store). Thanks any info would be very helpful. And great post all the way around.

  • Justin K says:

    I know the focus is supposed to be on the hats (which are all beautiful), but I want nothing more than that cropped navy trench. Stunning. Happy 2012.

  • Joey Dee says:

    Happy belated new year to yu and your team. Thanks for another great year of tips and ideas. May 2012, bring you all light, peace and prosperity at the style blogger!
    Joey Dee

  • Ambyr says:

    The herringbone cap and the fedora are my favorite. You have a snazzy looking team, love it. Check out my first menswear photoshoot on my blog today! Happy Wednesday.


  • Dani says:

    Hello Townsend :) Looking good…

    And as for Dan, gotta love the crisp trench (how come navy blue is always so handsome?!)


  • PewienPan.pl says:

    Very nice hat and tie on the last photo.

    All the best,
    Marcin from Poland.

  • MOZART5000 says:

    Barker Black make some of the most amazing shoes. They’re stunning. Can’t wait for my first pair.

  • JAMES says:

    This is off topic, but why is there never any picture of you wearing a three button suit? Thanks for answering, though it’s off topic, thanks.

  • JoeB says:

    Hey SB! Do u know what kind of boots alex is wearing as he dangles from the tree? lol thanks, nd keep up the good work!

  • HarrisonK says:

    Nice post. I’ve actually never really seen a younger man wear a fedora hat like you do. I think it’d be hard to pull off in some locations, even urban places (such as DC). I also would think one would have to be pretty “established” to pull a fedora like that off. I can’t imagine a college student being able to wear that appropriately. What are you opinions on how to pull this off?

    • Oli says:

      Make sure you wear it with confidence, and dress appropriately with the rest of your outfit. Avoid this look at all costs:

  • Emanuel Iuhas says:

    Nice post!
    Thank you!
    I like Wesley’s outfit…and hat of course!

  • Repair says:

    yeah SB..i sure did not know that …thanks for enlightening..

    Believe it or not, there was a time, not very long ago, when a man wouldn’t step outside his house without a hat on

  • RismoMax says:

    Nice scarf Wesley.

  • cam says:

    hey dan and team. never been a hat guy but what great outfits here!!!!!! major swag!