Smooth Separates feat. Ontario Amrstrong

September 13th, 2013

I first met Ontario Armstrong on the set of NBC’s Today Show in the Fall of 2009. He was one of the five finalists for Esquire magazine’s “Best Dressed Real Man” contest.

Shortly thereafter, capitalizing on the press and creditability that came along with the nomination, he teamed up with a fellow Esquire finalist from Philly and started a line of luxury pocket squares.

Armstrong & Wilson is going on four years now and business is good, thanks in part to their ability to get the squares in the breast pockets of celebrities and influencers such as Lebron James and Yassin Bey (Mos Def).

That said, nobody wears the squares better than the man himself. Here he shows us how he rocks them; always tailored, but usually in separates rather than suits.

     1. Burgundy & Navy


    “This Burgundy DB has to be one of my best finds from this vintage spot that I frequent in Philly.

    It’s a color that I typically wouldn’t go with for a jacket, but once I pulled the complete look together (pairing it with browns, tans and navy) I felt it made a bold statement, in a good way.”


    “The little butterfly pin was something cool I picked up at an estate sale… I like little subtle touches like that, after all, I’m an accessories designer.

    The watch was another great piece that I came across while shopping for buttons (the distinct detail of an Armstrong & Wilson pocket square)… I love it! It’s a vintage Elgin self-wind watch. I have such a connection with it every time I reach down and wind it.”


    “The pocket square and tie are from our latest S/S 2014 collection.

    As business has grown, we’ve extended into the neckwear business as well…with future plans of adding small leather goods, and perhaps a children’s line…”


    • Vintage Burgundy DB
    • Custom White Windowpane Shirt by Nordstrom
    • Navy Trousers by J. Crew
    • Brown Linen Tie by Armstrong & Wilson
    • Tan and White gingham check Pocket Square by Armstrong & Wilson
    • Oxblood Loafers by Johnston & Murphy

    2. Pinstripe Break-Up


    “I like to consider my style ‘Classic Cool’ – not too boring and not too flashy. It’s funny how my personal aesthetic is mirrored in the design of our accessories. Our approach has always been to mesh classic with a little edge.

    I’m a sucker for a nice DB and navy has to be my favorite color. I was definitely sold on the white buttons…It gives it an extra pop and feels lighter in the summer.”


    Props to Ontario for pulling-off the bold pinstripe suit pants as separates! Not an easy thing to do while looking so natural.


    “Accessories are the final touches that no gent should go without!

    This tie is my favorite from our upcoming S/S collection. The texture, the super-subtle stripe and the contrast back were all carefully thought out… A well-designed accessory can make a statement without being all in-your-face.”


    • Vintage Navy DB
    • Blue Dress Shirt by Brooks Brothers
    • Custom Navy Pinstripe Pants
    • Brown Striped Linen Tie by Armstrong & Wilson
    • White Linen Pocket Square by Armstrong & Wilson

    3. Dressed-Up Jeans


    “All in all, my style has always been a reflection of my personality…laidback, approachable, respectful.

    Here the jacket is a custom Hickey Freeman that a got years ago while working at Nordstrom… It’s one of those jackets that you can pair with almost anything.”


    “Of course I had to finish it off with the Armstrong & Wilson navy linen tie and our navy/white windowpane pocket square.”


    “My Sebastian McCall Jeans are by far the best jeans that I own. They’re a classic wash that I use throughout my wardrobe.

    And of course, the oxblood tassel loafer can be an every day shoe.”


    • Grey Plaid Blazer by Hickey Freeman
    • Custom White Dress Shirt
    • Blue Jeans by Sebastian McCall
    • Two Tone Grey Linen Tie by Armstrong & Wilson
    • Navy & White Linen Pocket Square by Armstrong & Wilson
    • Oxblood Loafers by Johnston & Murphy

    Thanks, as always, for reading and special thanks to our friend Ontario for participating!

    Yours in style,

    Dan Trepanier


    Photography by Alex Crawford

    • Theguybehindthelens

      I love the vintage vibe of the first two looks. They are sharp as well. Some great ideas here on how to wear the DB blazer I just picked up.

    • Sharul

      Awesome spectacles !! may i know what brand of it ??? and where…thanks ! Keep it up TSB !

    • http://undefined Jeanscuffed

      Hail to all 3 outfits!!

    • Tee

      I really like the Ontario Armstrong post as many stylish men and women you have had on the site I would have to say he has been the freshest keep up the great work I really enjoy this site.

    • Micky

      What’s up with the LA content?? We need more of you Dan!!

    • Desmond

      All top looks but number 3 takes the cake for me – hits the sweet spot between dressy and casual

    • Omar Shaikh

      Those wholecut lace-ups in look two are beautiful.

    • BF


    • Gazman

      Isn’t the word ‘separate’ not ‘seperate’?

      • Dan Trepanier

        Yes, thx

    • Rob

      That puff fold on the third is perfection

    • cam

      this guy always looks great and what stands out most, to me, is the perfection of the tailoring…the ties look exceptional btw

    • Andrew

      I would never think to rock pinstripe pants with a solid jacket. Interesting…

    • LouCaves

      Ontario, those looks are nice. I usually do separates; rarely wear suits.

      All the looks are tight (especially L1).

      I will be biting (80’s slang for “copying”…ha!) a few of the ideas here…with my own twist, of course.

      Thanks, TSB.

    • Adrian

      Solid outfits across the board Ontario. I actually just thrifted those same loafers yesterday. Great feature !

    • rey

      i have to add oxblood to my shoe rack