Summer Headwear featuring the SB Team

August 10th, 2011

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One thing I try to highlight on the site is the importance of seasonality in a wardrobe. Whether it’s clothing, shoes or accessories – there are options appropriate for every season.

Last month the SB Team and I were invited to meet the good people behind legendary American headwear powerhouse Stetson. We were given an inspirational tour of they’re historical NYC showroom (check out the amazing brand history!) and given our choice of some of the best Spring/Summer headwear on the market.

Here, a taste of how we’ve been rocking our new favorite hats.


1. Raffia Porkpie

A straw porkpie in a natural color is the first hat you should pick up for the Spring/Summer.

Bonus Tip: Wear it loosely on the back of your head for a laid back beach-town feel, or pull it on tight for a more serious and structured look.

Bonus Tip II: All the pieces in this look (straw porkpie, knit shirt, hopsack trousers, and leather strap sandals) work great together because they each fall somewhere between “dressy” and “casual”.

Bonus Tip III: Knit shirts are the sh-t. More on this soon.


  • Brown straw porkpie hat by Stetson
  • Burgundy knit shirt by Theory
  • Grey hopsack pants by MAB by Dan Trepanier
  • Brown leather strap sandals by Stubbs & Wootton
  • Watch by Montblanc Timewalker Automatic
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  • Ace F.

    Dimagiba? Is Wes a Filipino?

    • Westley Dimagiba


      • Ace F.

        Wow. I am very proud to hear that.

        Im also a Filipino but residing here in the Philippines.
        I should say that this site is very educational specially for a guy like me living here since mens fashion here are kinda like a cliche. Id say boring. Very lucky to find an awesome site like this. Im learning something about fashion every time i read an article from here.

        Keep up the good work guys!!!

        • Westley Dimagiba

          thank you Ace that means a lot.

          I understand what you mean, I was there last year visiting family in Pasay City and ended up going real casual the whole time.
          Glad you enjoy the site, mabuhay pare!

  • agung

    I love raffia porkpie style, especially a Knit shirt.
    I’m big fan of you sir dan! #Indonesia

  • TO

    The colour of that first shirt is amazing! Great pick-up. Looks are all excitingly fresh:) Photography is fire in this one Brent!

  • Bosun

    I have never really been much of a hat wearer,but this certainly will make me rethink. Really like the hat and look in the first two pics.

  • Square_face

    Hey SB,

    What recommendations do you have for someone with a square face?

    Newsboy caps just look funny on me…

  • Bobby

    I love Alex’s taste/style. Probably because i am from the south.

  • Windsorite

    Townsend is definitely now the best dressed dude on your blog!!! Keep it rocking.

  • Mountain Dandy

    I’m a big fan of the fedora and the newsboy cap. These guys look great. I have never really liked the look of wearing it back on your head, but that might be because I’m bald.

  • Desmond K

    So I’m really diggin the newsboy cap that Townsend has on. Searching ebayyyy NOW….

  • ramsay

    Very nice looks….Dan, as always, you never let us down!Truly the master of style….Keep up the excellent work!

  • dre

    Stetsons are great; Borsalinos are the best. Great write-up! I’ve been rocking a hat all summer long; one important tip is to make sure you bring a hanker-chief in order to wipe your sweat off the brim (could lead to pimples if not).

  • Cory

    Nice. Looks like my hat collection! Most of my hats are from Brixton and Gorin Bros., though.