Breaking the Rules in Style feat. Jay Gagnon

December 9th, 2013

Last month at the private opening of the Zegna store in Beverly Hills Alex and I rubbed shoulders with Edward Norton, Gerard Butler, Sharon Stone, and several other A-listers, but I was most excited about meeting Jay Gagnon – in his layers of cashmere and 3/4-length tweed trousers. We chatted for a bit, shared a smoke, and set up a photoshoot so we could share his amazing personal style with you.

You know when you watch a commercial for a sportscar ripping around a corner at 150 mph and on the screen is says something like “this is a professionally trained driver on a closed course – do not try this at home”. Well, Jay’s style is kind of like that. As the former visual director of Giorgio Armani, and now Ermenegildo Zegna, he’s an accomplished professional when it comes to creating visual experiences.

“Growing up in a small town in Maine, I always had a thing for clothes. Unfortunately I didn’t have access to a lot of options when it came to choosing those clothes. Thankfully, I have a great mom who understood my interest. She would take me on shopping trips to the mall once a year. We went to LL Bean, The Gap and a men’s store that sold lots of suits… Funny how those trips somehow led me to a career in New York City.

I think it’s important to dress as yourself and put things together in a way that says something about your personality and background… I always wear things that look handcrafted. I guess that’s because I always saw my mother and grandmother knitting, and wearing sweaters from LL Bean. I also have a great appreciation for modern design and updated fit from working at Armani. And finally, my love for classic, masucline styling comes from my work at Zegna. I like to mix all those elements and that’s why I buy the pieces that I do, and how I put together my wardrobe.”

Here Jay proves the old menswear adage “you have to know the rules before you break them” with three inspiring casually-tailored looks.

    1. Blazer & Sweats


    Photography shot with the Canon EOS 70D digital SLR camera, with Dual Pixel AF technology and built-in Wi-Fi

    “You can wear unexpected things under a classic blazer, like a chunky knit or fair isle sweater.

    I also like the juxtaposition of a blazer with a sweat pant or cargo pant.”


    The sweater here is a perfect middle-ground for tying together the sharp blazer and cozy sweats. It’s dark and dressy looking, but also soft and comfortable.

    Not to mention it’s a great compliment to Jay’s salt & pepper beard.


    “A good boot can be worn with everything.”


    • Navy Wool Blazer by Barney’s New York
    • Navy and White Turtleneck Sweater by H&M
    • Grey Sweatpants by Adidas Silver
    • Brown Leather Boots by Frye

    2. Socks & Sandals


    Jay and I are both huge fan of chunky scarves. The chunkier the better.

    “Scarves are the best accessory. This is my favorite because it’s super warm, extra long and has this great one-sided fringe.”


    Don’t buy 10 cheap scarves.

    Buy one impressively high-quality scarf and wear it all season. Like sweaters, scarves are easy to distinguish between high and low quality. It’s hard to fake a good knit because ultimately it comes down to the raw ingredients.


    Ask someone: what is the number one fashion faux-pas for men? More than 50% of people will agree: “socks with sandals”. Here Jay proves that these “rules” are simply a matter of taste.

    “Don’t be afraid to spend money on cool shoes, they’re the most important part of any outfit… You can tell a lot about someone from their choice in footwear… I can wear these all summer, or with a pair of chunky socks in the Fall. ”


    • Grey Wool Scarf by Yves Saint Laurent
    • Blue Jean Jacket by Gap
    • White Polo Shirt by H&M
    • Black Wool Vest by Neil Barret
    • Silver Ring by William & Madge
    • Leather Belt by Lanvin
    • Pleated Khaki Pants by H&M
    • Black Leather Sandals by Marni

    3. Tailored Hoody


    “When choosing a garment, the fit is the most important factor (thank you Mr. Armani).”

    But that doesn’t mean it has to be slim and streamlined. Fine tailoring comes in all shapes, sizes, and tastes. It’s more important to find a silhouette that works for you and keep things in proportion. Jay, for example, often wears his trousers full-cut, low on the waist, pleated, and cropped at the hem. It’s one of his signatures that he’s perfected.




    Someone new to style is probably doing too much. With experience comes an appreciation for subtlety.

    It’s the small details in Jay’s outfits that really stand out to me. Details like the more causal top-stitch on the blazer in look 1, the ring and belt in look 2, and the sheered vamp of the loafers here.


    • White Dress Shirt by Zzegna
    • Black Hooded Vest by Dior
    • Grey Donegal Wool Pants found at a shop in Milan, no label
    • Black Coat by Black Fleece
    • Black Loafers by Marc Jacobs
    • Metal/Leather Cuff by Emporio ArmaniBl


    Thanks, as always, for reading and special thanks to Jay for participating!

    Yours in style,

    Articles of Style


    Photography by Westley Dimagiba

    • Josh

      Does anyone know where to find pleated khakis like that now? J Crew had the union pant which was similar, but much slimmer fitting. The color/weight of the fabric along with the pleats is what I’m looking for. They’re going to get tailored regardless.

    • http://undefined Dick Lickerson

      Jay obviously is a creative guy, but in outfit #1 he looks like my drunk uncle when he stumbles in on Christmas dinner railing, “I could’ve been a Doctor!”, right before he budweiser-farts on the ham.

    • Dacian S.

      I think he looks like a hobo.

    • SL

      I do wonder if he’ll be able to look at these pictures 10 or 20 years from now and still think he looks stylish.

    • dave

      I’m all for developing a personal sense of style and expressing it without reserve. But will somebody please explain to me why this homeless look would get you a good see in any restaurant in town

    • Jason S

      Some rules are made to be broken but sweatpants and a blazer??? I don’t care how well tailored your blazer is, you still look like a homeless person wearing that combo and I won’t even get into the odd “Capri like” length of this particular pair of sweatpants.

      • Dan Trepanier

        Do homeless people wear blazers and sweatpants? You’re not the first person to say that. I’ve encountered my fair share of homeless people, but never noticed this phenomenon.

        • Jason S

          Yes, I have seen them in blazers but I must admit I’ve never seen anyone walking around in public looking anything like this, but warmth above all else seems to be the only reasonable purpose for combining these items. To me it almost looks as though he is making fun of your website by putting together the most preposterous outfits possible just to see if you will post them. This whole post could have easily been mistaken for an April Fools Joke if this weren’t late fall. I’m sorry if this offends you. I TRULY appreciate the style of most everyone featured on your site, especially your own. Your personal fashion sense has always come off as impeccable. However, I just can’t get on board with anything this article represents. Seriously, this guy really works for Zegna? That is a dream job yet with every one of these outlandish combinations he appears to be giving the finger to the whole fashion industry.

          If I had not seen so many great features before stumbling upon this one I think I would have written your site off instantly. Fortunately I know there are lots of great articles and much can be learned from the valuable information provided free to us all, right here. Thank you for all that you and your dedicated staff are doing. I’m just not 100% convinced that Jay Gagnon isn’t playing a prank on us all.

          • AirstreamStyle

            Over a year later and I stumble upon your new site. I could not resist looking up the article that made me lose all respect for your taste in menswear. All three of these outfits still repulse me as much as they ever did. Sad when lose respect for someone, even sadder when your hero, Dan, keeps your respect while wearing sweatpants, socks and sandles, high waters, basically anything.

            Oh well, looks like your still doing alright. Congrats on another new website. Still, I will never look to your site for fashion advise again.

    • Marcus

      Personally there is nothing on this particular post that appeals to me nor would i seek to replicate any of the outfits. That being said, whether you love it or hate it this article has generated sh!t loads of comments from everyone and its obviously sparked some debate. which i suppose is a good thing.

    • Bob Mack

      I have had a bit of a challenge trying to pair luxury brand blazers with more casual items, and I think its always inspiring to see someone accomplish this without having to resort to dark denim.
      I actually quite like the joggers/sweater/blazer combo Jay is wearing, and think i will try this myself soon.

      That said, I am a little perplexed by the untied boots. it seems less a casual statement and more of a careless one… Can you really walk comfortably with your laces untied like that? I would imagine you would wobble and trip on yourself?

    • Henri

      This isn’t breaking the rules. This is attempting to match pieces which simply don’t function nor work together.

      • HC


    • BougieHippie

      Impeccable styling! I like his play with cut, lengths and fabrics.

      His smile isn’t a bad accessory either!

    • Anonymous

      Some people just don’t get it. Its like they just want every story to be about the same old suits. what a challenge menswear blogging must be. This is why Dan is lightyears ahead of everyone else in the game – vision.

      • Juan

        If I wanted to see “the same old suits” I’d go to my nearest Canali store and get a catalog. It’s not about wanting to “see the same old suits”. I’m 21, most of the time I’m wearing a suit is as separates!
        It’s about being innovative in a purposeful way. I simply don’t see a purpose in wearing sweats with a blazer (not to mention the fit and proportion in look number 1, aka possibly the two most important things, are WAY off; again: why have the pants hemmed in a way that shows two inches of skin between the pants and the socks? It not only looks bad but you’d probably freeze your a– off too!), or socks with sandals.

    • Jeff

      I, like many on here, can’t say I’d mimic any of these looks. But there are two lessons I did pull from this feature:

      1) You can wear just about anything — and look good — with the right amount of confidence.

      2) Fit and colour-story can create an almost illogical cohesion between items that would traditionally look obscene together. Even at his most eccentric, Jay looks 100% put together.

      Thanks for the thinker, TSB team.

    • http://undefined John

      I’ve been conditioned for some time now that the narrow, plastered-to-the-body look is the standard. Jay champions a point of view that advocates for the one size doesn’t fit all; he advocates for individuality, non-conformity. Mr. Gagnon: you wear non-conformity well sir. Thank you.

    • Brandon

      The biggest thing I took out of this feature was the fact that the visual director of Ermenegildo Zegna, no doubt able to buy the most exclusive mtm Zegna suits and tailoring, wears stuff from H+M.

      • Drew

        haha so true

    • Misha G.

      I have the same H&M pants Mr. Gagnon wore in look 2, but mine are more slim. Interesting and cool to see it in a different way!

    • Richard L.

      That’s cool. I have to admit, at first I thought the “Featured Items” would be: “______ by Zegna, ______ by Zegna, ______ by Zegna, _____ by… etc” lol

      I wouldn’t think of doing these outfits myself, but it is forcing me to think about being creative without looking like I’m trying too hard.

      Great feature.

    • Brady P

      Big fan of the sweatpants with the dressier sweater. The blazer on top is still to high/low for me… But I love to see the professionals show their sense of style. Great post!

    • Juan

      This post is full of “trends”, which is why I don’t like it. As always, I appreciate the amazing work you guys do, but I feel this (as well as some other posts lately) defeat one of the purposes of this website, which is to not get caught up in trends and display looks that are timeless.
      Rules ARE meant to be broken, and I understand most “timeless” looks must seem boring to a guy with Jay’s credentials, but I believe that while you can wear white after labor day, and your jacket mustn’t cover your rear at all costs, you simply can’t wear mid-calf sweatpants with a tailored jacket and boots, showing a good chunk of skin between your socks and the hem of your pants. It looks off, and breaks the proportion rules you guys have been talking about for going on four years.
      Also, while I understand the point, wearing sandals with socks definitely defeats the purpose of wearing sandals and/or socks.
      It just seems that the rules were broken here just for the hell of breaking them (as opposed to, for example, the “no white after labor day” rule, where the point is to wear white pieces as canvases for elaborate and daring patterns/colors/fabrics, creating contrast and a pleasing experience for the eye).
      With that said, I appreciated this since it showcased some exceptional pieces, such as the trousers in look 3; I live in Milan and would kill to know the name of the store got them from!

      • Jack

        You said what I couldn’t say. I feel like if I oppose some of these foward looks I’ll get labelled a hater by the team. I just don’t feel like this is something that is different in a cool way. It’s just different.

      • cam

        @Juan – i’m curious as to how/why you can speak to the purpose of this site?

        • Juan

          @cam – Sorry if my statement came off as pretentious, I know it’s not my place.
          I’ve been a follower for a long time (since the late blogspot days), and as long as I can remember, Dan and the crew have always tried to come up with timeless looks. I clearly remember reading one post a while back that said “you don’t want to look at pictures twenty years from now and say ‘what the hell was I wearing?'”.
          As far as I know, although I could be wrong, from what I’ve read in these past 3+ years, the guys have always advised to avoid trends “like the plague”.
          This post is full of them, and while I myself may follow some trends (my torso is much longer than my legs, therefore I have my tailor hem most of my coats and blazers/suit jackets), these trends have a purpose (in my case the shorter jackets make my legs look longer and balance out my “frame”). Honestly I just thought it seemed fair to point out that, while I almost always agree that rules are indeed meant to be broken (we’d still be regularly wearing morning coats if they weren’t), I really don’t see the purpose of wearing mid-calf jogging pants with a blazer, showing a couple of inches of skin between the hem of the pants and the socks. Same goes for the sandals + socks look; but to each his own.

          • cam

            @Juan – not pretentious at all. while I agree to your point about the site’s roots in traditional and appropriate menswear, it is clear to another regular follower, that the site has taken a broader approach to style more recently. dan has many times mentioned the idea is not to replicate particular looks but to draw inspiration from them. maybe you don’t wear a blazer with a jogging pant or trousers with a vested hoodie, I honestly wouldn’t hope anyone outside the fashion/ #menswear industry would do so. but maybe you do decide to wear a blazer with a patterned sweater or a full cut trouser with pleats. just don’t do the sock/sandal thing ;)

    • Cory

      No. No. And no. Doesn’t work for me. I love much of what Zegna makes though. My most cherished article of clothing is a Zegna sport coat in tonal windowpane navy wool.

    • scott

      No offense, but dude looks homeless.

      • Alex Crawford

        Must be some fancy homeless people where you live.

        That being said, you don’t have to have a home to have great style. I bought this hat off a homeless gentleman in San Francisco:

        • scott

          It’s not that the clothes look cheap, it just looks random like he put on whatever he could get. There’s no fluidity through the outfits with mismatched everything..

    • Ace F

      ala Nick Wooster.

    • Anon

      Love it. Love TSB!

    • Bob

      Style rules are meant to be broken! Nice work

    • Vsepr

      I can’t really understand dudes outfits, but he’s obviously at a level that most dudes will never reach. It seems regular outfits got “boring” and now he’s like Jordan on the Wizards player coachin ninjas

    • AK

      I understand that this guy has credentials, and so I feel silly criticizing these looks. But I have a few thoughts:

      First, in my opinion, it is impossible to dress up sweatpants, especially when they’re flooded, and that pair in particular comes dangerously close to capri territory. If the goal was to use them to dress down the outfit, I just don’t think it looks good. To be frank, I feel that it looks sloppy and affected. It seems to me that some rules can be broken while maintaining a sense of coherency and purpose, while others simply can’t.

      On that train of thought: socks with sandals. A contradiction. It neither looks good nor makes sense. Sandals free the feet and let them breathe, socks contain the feet and keep them warm. Again, I get the whole “breaking the rules” thing, but trespassing on another’s property is much more innocuous than murder. Socks w/sandals are the style equivalent of the latter, haha ;)

      Don’t mean to come down too hard on Jay. There are many things I like about his style, particularly look 3, and I’m sure a controversial post such as this is meant to bring out some detractors. As always, I appreciate what you guys do here.

      • TimL

        My thoughts exactly.
        I like different types of style but:

        sweats outside of the home or working out….. never!

        socks and sandals….. these have never mixed for me and all the kids in my town wear them and I hate the look. Make up your mind, it’s either hot or cold but that look will never work for me.
        The last look is ok.

    • TO

      Oh man, this will undoubtably cause a stir. But, I think Mr. Gagnon looks COOL here. Not necessarily convinced about socks+sandals but I don’t think Mr. Gagnon cares about that being my view, which is why it works for him!

      I actually wanna see the Black Fleece coat he is holding in look #3!
      1st look if my favourite- for some reason to me it looks so ‘familiar’ that the rules need not apply. Weird I know.

      Somewhat rural humble beginnings translating to NYC clothing industry where have I heard that before… :)

    • http://undefined Steve B.

      I think all of the looks work— on him! He really does know how to break the rules and does it with such confidence; a mere mortal like me would look like a clown if I tried any of those looks (except maybe the scarf) ;-)

    • Shawn

      Interesting looks, even though I wouldn’t wear any of those. You really got to have a job in the fashion industry to pull off looks like these and be respected and regarded with high esteem. Props to this man!

    • only says inspiring


    • Chris

      Dope. I’ve been feeling pleated pants more and more recently.

    • Austin

      Looks two and three have me #feelingsometypeofway, something about those wool trousers in 3 is drawing me in, the pleat and the way they are cropped remind me so much of Yohji Yamamoto. Seeing someone pulling this off so effortlessly is refreshing, keeping menswear fresh and interesting can be a difficult task, you guys are definitely doing it.

    • Owen

      Great, thought provoking article. I’m just learning about fashion/style and this really made me think about what style is.

      I mean, to the regular guy on the street who knows little about style (myself included) Look 1 seems confused. To the untrained eye it looks like he got dressed in the dark the morning after a Pearl Jam concert. And from a practical point of view, why wear a warm jumper then have your ankles showing?

      I’m just learning the rules so I don’t have the confidence to break them. But what about breaking so many rules that what your left with is not style but personal eccentricity?