How I Wear MY Square, ft. Ontario Armstrong

July 12th, 2011

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As I’ve written in the past, a pocket square is a small accessory that can make a big difference. Few men understand this better than Ontario Armstrong, fellow finalist for Esquire Magazine’s “Best Dressed Real Man in America” and charismatic co-founder/designer of the new style-forward pocket square brand Armstrong & Wilson.

A few weeks ago Ontario traveled in from Philadelphia to catch up and share a few looks to show us how we rocks his new squares.


1. “Mr. In-Between”

“A casual summer look like this one is what I call the Mr. In-Between - not too dressy, not too casual. I’m not big on bright colors, so I tend stick with an neutral palette and use color in smaller accents. When I’m not in the mood to fold my square I like to throw-and-go, I think it adds character to any square when you toss it in your pocket without over-thinking it.”

Bonus tip: This post could also be named “1 piece/3 ways: tassel loafers” (which we already shot, here)

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  • Anonymous

    I wore that JCrew chambray shirt today with some chinos and navy saddle shoes and decided on a whim to stuff a red floral print hill-side square in the shirt pocket before walking out the door. I think it looked cool and added just a little something unexpected to the outfit.

  • Mountain Dandy

    I love the square in the pocket….and in the vest.

  • TommyK

    Loving the pocket squares SB!!

  • Krupott

    that one grey jacket it a bit tight and the shoulders look a bit like texas.

  • Another Dan

    I never thought of putting a pocket square in so many places. Great post, and I can’t wait to see the suit + shorts one.

  • Pjom

    Anyone know if h&m is still carrying that jacket??

  • Mr. Andy

    Loving the PS in the back pocket.

  • OArmstrong

    Thanks to all the readers for the great feedback! Yo Dan, it was definitely a pleasure working with you on this shoot. Thanks again brother.




    Nice post as usual! Can you give us the details on Ontario’s shirt and watch in the first pic?

    Thank you.

    Stay Fresh,


  • Sylvan

    Trespain, you look awesome in those shorts and jacket. That is so well done and inspirational. I mean the essence of style, design and sartorial finesse. Who else can pull that look than you bro. Absolutely marvelous and amazing. You my friend are a stylist, designer and fashion fabulous mogul.

    • SB

      Thx for all the compliments!
      Our best stuff is def still to come.

    • Krupott

      what shorts?

      • Krupott

        Nvm i located the pic with thestyleblogger wearing some shorts but he is very difficult to see because he is all camoflouged and in the far side of the frame. things are gettin nastay on this blog

  • Emanuel Iuhas

    I’m trully in love with pocket-squares since 2 years ago (when I travel in Italy)…I have a collection of more than 50…
    Lovelly post , adorable looks…
    Thank you Dan & Ontario!

    Emanuel Iuhas
    Visual Merchandiser/Fashion blogger

    • SB

      Can’t have too many squares.

      Thx for reading.


  • Michael

    FANTASTIC Levis. What model are they, if you know?

  • PocketSquareZ com

    Nice style in the back pocket.

  • Elijah Bernard


    I’ve been looking everywhere for these pockets squares and can’t find them! all of the outlets from their facebook page are no where near NYC or Houston.

    Any help is greatly appreciated.

  • Morry

    I really like Armstrong & Wilson pocket squares and I think it’s awesome that they’ve been featured on this site.

    • SB


  • Boyd Brown

    Where does Ontario get those bang-up buttons for his pocket squares? I saw a lot of gents rocking similar flowered (buttons) ones on their lapels at Pitti Uomo. I need to get my mitts on one! Dig your work SB, Blog-on.

  • Jquon

    Wow, really shows the versatility of a pocket square. Who knew?

    I’d like to see a better shot of the work shirt, paisley suspenders, and denim.

    Love the blog!

  • StormCloud

    Check out back pocket hanky code:

    • SB

      hah. I can assure you this has nothing to do with Ontario’s intention.

      Thanks for reading,

      • Kip

        Intentional or not; signals get sent. Thanks Storm, that was my thought when I saw that picture.

    • James

      hahaha ha

  • Windsorite

    Hahaha it’s Steve Urkel in look 3, definitely a “geeky” look.

    • SB

      More like Stephon (you know, when Urkel goes into his homemade swag machine)

  • O Williams

    Hello my friend.

    Classy as always,
    but Dan I’d like to see you with a little tan.

    Greetings from Switzerland

    • SB

      Haha. Word.

      We shot this about a month ago – before the beach!

      Thanks for reading.


  • Miguel Ramalhão

    I’de never thought of the back pocket!… Nice idea.