Smooth Separates feat. Ontario Amrstrong

September 13th, 2013

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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
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  • 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