Weekend Tailoring feat. Neil Watson

September 11th, 2014

The menswear world is a small one. You go to enough events, trade shows, parties, etc. and you start to see the same familiar faces. Introduce yourself and you’ll also learn that you have five mutual friends in the business. That’s what happened with Neil Watson. Alex and I first bumped into him at the MRKT tradeshow last year, where his tailored look was a clear standout.

Turns out he’s a fellow Canadian menswear enthusiast based in Toronto, and we have several mutual friends including the always sharply tailored Angel Ramos and Khaled Nasr.

On top of being a street style photographer with a keen eye for detail (he shot our recap of menswear trends at Pitti Uomo this past summer), he also has an incredible Italian-inspired casually-tailored sense of style.

Here he shows us how to look sharp and smart in tailored pieces for the weekend.

    1. Early Fall Over-Shirt


    “Like most of my friends in the clothing business, we never intended on being here. I was set in my first year of University to be a lawyer. Fast forward a few years and a bad break-up later, I was encouraged by my now fiancé to delve a bit deeper in menswear than just showing up to court every day in a thoughtfully coordinated suit and tie. In my last year of school, I graduated under the guise of ‘pre-law’, all the while working full-time at Ralph Lauren and graduating from sales to buying.

    The back-end of menswear is a funny thing; you see the true value of goods and learn how pieces move from demand, to design, to production, to distribution, to the end consumer. I enjoyed learning the ins-and-outs of the supply chain, but the spreadsheet life eventually grew old on me.

    I was seeing so much going on that I wanted to talk about. Namely the hardships of entrepreneurial life in fashion, and how often new designers would fail and start all over again… This business is very volatile, more so than most new players realize. So two years ago I began as a contributor for A&H Magazine, and slowly realized that this was where I wanted to be… Today I’m the Editor in Chief and we’re on our way to an independently funded print magazine.”


    It’s still warm out, but getting a little breezy. Think of a shirt in a heavy fabric (like a rugged denim) as your first piece of outerwear during this seasonal transition.


    The only casual belt you need in a rotation is a light brown woven leather, something like this one by Ralph Lauren.

    Neil_20 Neil_21 Neil_22

    • Glasses by Oliver Peoples
    • Denim shirt by RRL
    • White shirt by E. Zegna
    • Leather woven belt by Ralph Lauren
    • Khaki chinos by Loro Piana
    • Navy canvas tote bag by Filson
    • Watch by Cartier
    • Suede loafers by Christian Kimber

    2. DB + Gilet


    “I always identified with clothing and had a strong sense of what I was wearing. When kids my age were worried about catching the next WWE match on TV, I was thinking about the color coordination epidemic in my closet… Now with the advent of Tumblr and the like, I have catalogues of images to skim through. I try not to pay attention to what’s trending too much, though. The way I dress is heavily influenced by classic menswear, and starts with fit and proportion… To be honest I hardly think I dress well compared to my friends.”


    You won’t need an overcoat for a while – start with a lightweight quilted vest like this one. Wear it over an unstructured cotton double-breasted jacket in the same color for a very suave way to dress-up a t-shirt, jeans and sneakers.

    Neil_07 Neil_08


    • Cotton double-breasted jacket by Ian Velardi
    • Jeans by Dior
    • Sneakers by Superga x Brooks Brothers

    3. White Denim Year-Round


    “My advice for guys new to style is to start with what fits. Proportion is king. As long as you build a solid foundation based on fit and utility, you’re golden. After all that is said and done (which it never really is) you can tinker with your style, because it will always change, as you will always change.”


    Look closely at those textures. Those blends. Cotton/linen shirt, linen/cotton/wool jacket. Now that’s some transitional tailoring.

    Neil_14  Neil_16 Neil_17

    White jeans after labor day? Of course. Make them a little more fall-appropriate with a pair of light brown suede loafers.


    • Shirt by Eton
    • White jeans by Hudson
    • Suede loafers by Carmina
    • Pocket square by Cucinelli

    Thanks for reading, and special thanks to Neil for participating!

    Yours in style,

    Dan Trepanier

    Shop Custom Menswear Made in America


    Take me to the Shop

    • Caboom

      great article!! more of please

    • jaykaysway

      That first fit is money.

    • MaleStylePro

      Great to see fellow Canadians being featured. This really shows how far menswear has come in Canada. Guys are paying much more attention, to proportion, fit, and fabric.

    • Kolja Kassner

      Awesome looks, big compliments from Hamburg!

    • Kyle Leon Norville

      Absolutely refreshing .

      That first look is so simple yet intentional.

      This also seems to be the first article I’ve seen with no negative comments.

      :) I’m definitely not doing to be that guy either.

      Amazing editorial

    • Stuart

      An in depth look at casual weekend wear was long overdue. I love looks 1 and 3, especially how the jackets boast a slightly longer cut. Well done.

    • Khaled Nasr

      Wow!! What an amazing feature by my bro and amazing friend Neil!! We spent so much time at Pitti together and i am not kidding when i say he is one of the most talented and genuine people i have ever met. His photography is insane and his casual style is for me something to envy! Love you bro!!

    • Zane

      I love this quote “build a solid foundation based on fit and utility, you’re golden”.

    • Miguel

      All three outfits were on point, it looks like something I would wear, nothing out of this world but well put together with some fine pieces.
      Specially the last look, great stuff.

    • ChrisD

      Fit is so spot on, he’s mastered ‘slim’ without it being ‘skinny’.
      Though I wonder how much is due to alterations v.s. just having the body shape/proportion of the manikin it seems menswear is designed around.. haha
      Great feature.

      • http://www.themodestman.com/ Brock

        Yeah, takes a lot of effort for us non-mannequins to get those proportions down. Well worth it, though.

    • http://DapperAdvisor.com/ Akil McLeod

      All three looks are dope and I especially appreciate the detailed shots. Good Job!

    • Ali Naaseh

      TSB’s best feature TO DATE

    • TO

      Neil is the real deal. A truly interesting and engaging guy. His impeccable taste for clothing and amazingly coordinated outfits only begin to tell his story. What a nice feature!

    • Russell Tinsley

      White jeans + caramel suede loafers = supreme gladness



    • David

      Finally, TSB features style and not fashion. More of this please.

      • Looch

        Yes. Second that.

    • Juan Zara

      Great looks all throughout the article, but those Carmina string loafers take the cake!

    • Anon

      Really nice simple looks. I’m curious as to the size of the RRL shirt in the first look. Thank you

    • John B

      Really like the looks here. As Shawn said below, simple yet effective!

    • Looch

      Really digging bro’s aesthetic.

    • Vince Granado

      Is he wearing a Reverso in the first look?

      • John B

        It’s a Cartier Tank I think.

    • Shawn

      Simple but effective. Just like I like things!

    • Andrew

      That first look is dynamite