What I Wore Today: Tailor Game Strong

April 29th, 2015

Rule #1 of Articles of Style: bring your “A Game” every day!

“Tailor Game Strong”

Use the comments section below to tell us who’s style you’re appreciating today.



    Alex with his new California hair and goatee is my new style icon. Here he shows us that a double-breasted suit jacket can be worn as a blazer with jeans, even frayed ones. Just make sure the fit of the jacket and jeans is consistent, and you complete the look with some good accessories, as Alex is known for doing.


    • Panama hat Vintage
    • Blue striped dress shirt by Polo Ralph Lauren
    • Grey Double Breasted Jacket
    • White 511 Jeans by Levi’s
    • Black Leather Double Monkstraps by Just A Men Shoe

    DJ McDonald


    You may remember DJ McDonald from a post we did on tying scarves which resulted in one of my favorite photos we’ve ever published (see: gangster stripe suit in front of Barclays Center). Coincidentally he’s in NYC giving us his version of the db and jeans, complete with the statement-making accessories as well. I have to say, this is a great example of using staple menswear pieces to create a versatile casual look.



    Photos by Naimpressionz



    You already know I have a thing for pajama shirts. I like the simple shape, and the comfort. Maybe it’s a subconscious Heffner inspiration. Or maybe a Gosling. Either way, this silk pajama shirt and tropical wool trouser is perfect for a warm night out near the ocean.



    Rich Freshman


    Rich Freshman might just be the coolest menswear cat in LA, seen here with his signature tape measure and streetwear-x-custom-tailoring blend. You know we love a slim linen suit trouser, especially dressed down with some woven leather slip-ons, a scoop neck tee, and a lightweight Spring bomber. This guy really gets it.


    Thanks, as always, for reading.

    Yours in style,

    Dan Trepanier

    Shop Custom Menswear Made in America


    Take me to the Shop

    • Freshman

      Gotta give it to Alex. Dope on the lenses too. Didn’t see the DB coming bro… caught me off guard. – “Freshman” :|

    • Chris

      Alex destroys it again!!!! TKO!

    • N Caffrey

      Been reading TSB (oops) for a long time, and this is my first comment. Just wanted to give my upmost respect to Alex for his transformation in style. It’s very inspiring to see him discover his personal style and do what most struggle to achieve, and that is wear clothes that reflect exactly who they are, not what is trendy this season.

      • http://tsbmen.com/ Alex Crawford

        Thanks so much Caffrey, that means a lot.

    • Max BornInTheNineties

      Dan wins.

    • ALex

      Brand on DJ McDonald’s watch???

      • DJ

        It’s a Timex Watch. Strap is by Form•Function•

    • David

      Alex is who I want to be when I grow up. Can I still say that at 25? Haha everyone killed it today, but I think Alex gets the win this week.

      • http://tsbmen.com/ Alex Crawford

        Hahaha thanks David.

    • Alain T.

      All great outfits but DJ Mcdonald takes it. Never knew a trench by H&M could look so good.

    • AdamE

      Alex for the win… Dan would have had a chance, but in this case, i think the correct number of buttons to leave unbuttoned was n-1 (where n = the current number of unbuttoned buttons…), since that makes it look like pyjamas, rather than a pyjama looking shirt…

    • TO

      Appreciating everyone’s style today. This is one for the readers who have been complaining about WIWT outfits being too “fashiony” lately. Universally wearable, but far from boring looks. Alex and DJ take the cake today! Love the DB khaki.

      Still coming to Toronto?

    • Miguel

      DJ takes it today, even though Alex is not far behind.

    • Guest

      Alex by a mile…Dude is fly.

    • Erik J.

      DJ! His outfit is perfect.

    • Bryan S

      DJ, love the color of the DB with the jeans.

    • Herb

      If you cannot afford AMI, you cannot afford AMI. smh

    • tommyjohn_45

      Man.. huge fan of Rich Freshman’s style and ability. Great WIWT all around. Love the look of all four gents. Think I have to give it to Alex though, just being familiar with his progression… Really coming into your own, man, well done.

    • Sapprentice

      Nice WIWT for this week! Dan, I like what you did last time when you used a pajama top for layering. This time however, you’re wearing just the pajama shirt and it feels like something is missing. Still cool though that you wear a pajama shirt like that.

      This WIWT has one winner for me and that’s Alex. Nice outfit Alex, you look like a boss!

    • NorskeGentlemen.com


    • Ali Naaseh

      Alex takes the cake

    blog comments powered by Disqus

    All Navy Everything

    The Unstoppable Gray Flannel Suit

    How It Should Fit: The Overcoat

    A Guide to Vintage Shopping

    “Learn the Rules Then Break Them” feat. Ignacio Quiles