Light Layers of Fall, Part II: The Overshirt

November 18th, 2010

Here in NYC, the weather has been relatively mild lately. Perfect for another “light layers of fall” feature.

A quick, easy and unexpected way to add a little warmth and texture to your look on a mild day is by layering shirts. The trick here is to make sure the over-shirt is a heavier fabric than the shirt underneath it (as a general guideline – not rule – your fabrics should get heavier as you layer outward). Also, there is no need to size-up on the outer-shirt, you’d be surprised how much room there is under even your slimmest button-downs.

Here are three good outer-shirt fabrics, worn three different ways.


1. Cashmere Blend over Bowtie

When wearing two collars, it’s important that they contrast in silhouette. The under-shirt should be more pristine and closed at the collar, preferably with a tie, while the outer-shirt should appear loosely thrown on, quickly buttoned and be open at the collar.

I picked up this cool snap-front cotton/cashmere shirt for $18 at a mom-and-pop vintage store and it’s surprisingly versatile – I’ve already worn it with a blazer, under a down vest, and as outerwear.

  • Ali

    Killing that buffalo plaid look. Never once would’ve thought to wear flannel over a thin sweater, but rocked it this morning after I stumbled across this oldie.

  • Marshall Mulherin

    Mr. Trepanier this is genius. This post literally just saved a couple of shirts from being thrifted. Oooowee the possibilities iz g3ttin outta c0ntr01
    Haha but for real this is awesome

  • Oscar

    How tall are you?

    • SB

      6’1 without shoes

  • brooklyn

    What fit/wash are the Polo jeans you’re wearing in the first look? I notice them in every post that you wear them, because they just look like the ideal casual, med. wash denim.

  • Crispy

    Love the blog! I was wondering if you had any tips on the final polishing touches with the layering. For example, in the last look I love the layering and how it looks slightly off (i.e. any look at J. Crew.) Even having my clothes tailored I still have a very hard time keeping my layers looking effortless! Like showing my belt below a sweater without looking like I’m trying….

  • Anonymous

    hey man,

    i like the heavy shirt, and living in Toronto I’ve got access to tons of vintage stores that carry them. My only problem is that they fit large and kind of awkwardly – do you ever get them tailored?

    • SB

      Sometimes I do, if I really like the pattern/style of the shirt. Usually, though, I search the racks until I find one that fits well enough that I don’t have to spend any more money on it for alterations. Every shirt fits differently…wear a plain white t shirt when you go thrift shopping and try a dozen of them on. After you do that for a while, you’ll be able to eyeball the fit without even trying it one (paying visual attention to aspects like the shoulder point-to-point, the armhole size/height, chest width, sleeve length/width, etc.

      Hope this helps.
      Best, Dan

  • TrueBlue

    Hey Dan,
    Great post. What can be said that has not been said about your style and elegance. In previous blog you mentioned playing ball in Detroit. I actually grew in the 313. I heard of what a white kid from Windsor who used to ball with the brothas. Kid was so nice they called him “whitechocolate”. Please tell me that wasnt you man…

    • Yea!

      I’ve been acquaintances with Dan for a long time. The reference is for sure him.He was probably the best high school player ever from Windsor (he was the only ever back-to-back Mr. Basketball) and he put up serious numbers in Detroit. also his game was def very “white chocolate” all the way lol
      Keep doing you thing Dan!!

  • Christian

    I really love the herringbone tie seen in the second look, rather special.

    Best Wishes,


    • SB

      Thank you Christian. I will have more pieces that I personally design on here soon. Stay tuned. Thanks for reading. Best, Dan

  • 510

    I’ve been wanting that plaid buffalo shirt from JC for so long, but xl for that shirt was too small for my height. Glad that you have a piece that i wanted, i feel special now lol. The look you put together looks very comfortable on you. Keep up the good work

    • SB

      Hah. Thanks. Sounds like you need Tall sizing. JCrew has it, but it’s hit or miss. Try online perhaps, you might get lucky. Thanks for reading! Best, Dan

  • GP

    I like the style very much! ;) It’s fresh

    • SB


  • Anonymous

    Love all the advice here. I do remember in an earlier post you mentioning matching metals to metals and leathers to leathers. It looks like you are rockin either a cotton or black leather watch band in the first pick. I realize you probably shot all
    3 looks and maybe didn’t have time to change out the band but if you were to would you opt for a brown leather band in the first look? I know I’m being picky here but to me its in the details. Thanks

    • TO

      Before he chimes in with his opinion, I thought I’d take a stab at this- metals to metals, hides to hides, yes, but the watchband in this case is a grosgrain ribbon not leather so it doesn’t really fall under that “rule”.. that’s the way I see it anyway

    • SB

      The grosgrain watch strap is Navy blue, Olive Green and Burgundy. It’s a replica of the watch strap Sean Connery wore in Goldfinger when he played James Bond. Thanks for reading. -Dan

      • AldaArmez

        “The grosgrain watch strap is Navy blue, Olive Green and Burgundy. It’s a replica of the watch strap Sean Connery wore in Goldfinger when he played James Bond. ”

        Where can I find this for purchase!? Would do wonders on my Timex.


  • Terrence

    Very nice. I think I have that Polo button up you’re rocking in the second look. I loves it.

  • Brendon

    Well done sir. Ive seen a similar look on Prepidemic Magazine very similar to your 2nd look (Chambray and plaid) where they had a plaid shirt over a flannel but no tires. The way you pull the chambray over makes it look like the lightest of jackets.


    • Brendon


      and I might add, I like your look much better.

  • eupham

    I came across this on Valet this morning as I sip my coffee wearing a a chambray shirt, a hillside tie, and a vintage buffalo plaid over the top in leiu of a sweater or sport coat. The over shirt has been a staple of American fashion since the 40′s and 50′s. I’ve been doing it for years. One of my favorite ways to pul it off is a vintage oxford worn with a thin crew neck lambswool sweater and finally a heavy plaid over flannel on top worn open. Pair of dark jeans, some indy boots, and a tweed newsboy cap and I’m good to go. Layering makes me happy.

    • SB

      Well done. Thanks for reading. -Dan

  • fematt

    The gloves in the first are incredible. Amazing find. I just recently picked up these gloves,, but definitely would have much preferred something with such a unique weaving(?) pattern (unique for gloves that is).

    Not that you you’re asking for opinions but looks two’s shoes, matchy-match. A grey boot or white clark would have sealed it.

    • SB

      Thanks for reading, and for sharing your opinion! Best, Dan

  • Sabir P.

    I am a fan of the ideas overall, however; the chambray shirt look just isn’t really doing it for me. The 1st look with the bow tie is very well done. The weight of the layers for the 1st and 3rd look are spot on.

  • Chase

    I would’ve never thought of wearing a chambray shirt over a shirt/tie but i LOVE it! I’m definitely going to give it a try, you have a great eye, where do you get your inspiration from?

    • SB

      Thanks Chase! As far as the inspiration question, I could probably write a novel on that one. Short answer: anywhere and everywhere. Best, Dan

  • Travis


    You’re pulling off the first few looks for sure – not a look I would personally try to pull off – I’m not at Jedi status like you are. But the last look is killer and something I could get away with.



    • SB

      Haha. Thanks for the compliment. Sometimes it can take time to change people’s “perceptions” of you and your style…it’s better to start dressing better slowly over time so that people can embrace it. If all of a sudden somebody where’s something out-of-character, onlookers can become weary. Thanks for reading! -SB

  • donuts

    First time commenting here – dope blog. Nice to see fellow Canadian’s doing big things.

    One question, how do you make your denim selections? If you’re wearing a dark shoe/boot, would you recommend darker denim and vice versa? If there is a (general) ‘rule’ to be followed, would you apply it to other casual slacks as well?


  • DY

    I’m feeling looks 1 & 2… #3 is on point too but I’m just not ready to go back to plaid flannel.

  • JMRouse

    You hit the first look out of the park. I’m going to try and pull something similar off now that you gave me the idea. Posts like this are really helpful for me because of where I live. We don’t get that many days that are super cold, but plenty that looks like this would work.

    • SB

      You’re in luck, light layering is where it’s at! Although I can’t wait to start posting winter stuff too. Hope all is well JMRouse -Dan

  • SD

    I’m not sure I could pull off the collared shirt overtop another collared shirt, but you do it quite well! Great post.

    • SB

      It’s not for everybody, but hopefully it sparked some kind of new ideas. Thx for reading, SB

  • Zulhilmi Rahman

    Dear Dan T,

    Those are very pulled off looks. I’ve been trying those ever since but it never seemed to work out until I realized that everything is about balance.

    When combining patterns, just mix it, don’t match.


  • E. Santana

    Honestly not sure how I feel about the double button up look. Obviously layering is essential as the Fall temperatures drop, but I am always a bit weary of styles that seem unnatural. One should certainly be bold when establishing personal style, but such looks as this seem excessive. Frankly, I think that if one is not careful this particular look can be quite unflattering.

    • SB

      Well said. If not done correctly, or on the wrong person, this can look a little affected. It’s important to know your “level of personal style” and know what you can get away with. Thx for sharing your opinions. Best, Dan

  • Fresh2Death

    Whattup, SB?

    I am diggin’ the new post…my favorite outfits are the chambray shirt, and the vintage cashmere-blend (The bow-tie is sharp, Brooks Bros bowties are amazing)..really cool looks…I invested in the grey and blue chambray shirts from JCrew (although I like your R&B chambray better) and I love they way they are breaking-in…when I first started wearing them, I thought they were cut a little generously, but after the first wash they tightened up and I would never part with them.

    Great post, keep up the good work!

    Stay Fresh,


  • wya

    I have to admit, at times I disagree with some of your posts, but that is only natural. Despite the differences in style and opinions, innovating concepts like these are why I continue to return to your blog.

    It is also good to see you dress in a casual way, for those out there who, because of their profession or being students, do not get to wear suits every day. That kind of versatility is the foundation of asserting your personality through your clothes or, in fact, in whatever it is you do. Just like your “All black everything” (*ahem* hov nod) post is a great way to keep your readers see your multifarious styles.

    Great post and looking forward to more.


    • SB

      Thanks for your comment. Of course we’re not always going to agree. That is sort of the point. As I’ve said several times before, I purposely push the envelope of “classic”, “aggree-able” style that can appeal to most men. Some will inevitably agree, while others won’t…and the comments section is where we can breed such discussion. As far as versatility, I like to be a chameleon of sorts…keep people on their toes and avoid predictability.

      Thx for reading!
      Best, Dan

  • Anonymous

    Been doing this look for a bit and loving it. J. Crew green and black buffalo check flannel over denim chambray and knit tie with scrunched khakis and Red Wings? Damn right. Good piece.

  • cam

    really like the last look dan. still trying to digest the first two. thanks for the post

    • SB

      Thanks Cam!

  • Eric

    I have to give you credit; it seems like every post you put up, the clothing items I’m most intrigued by (in this case the wool herring bone tie) were the ones you just happened to design. I’m looking forward to your online store opening up!

    Keep up the great work.

    • SB

      Thanks Eric. Of course, I’m saving the best pieces for the official launch :)

      Stay tuned.

  • Jen Smith

    what great combos…you and my guy dress a lot alike….another great post….


  • DG

    I’m struggling with how to scrunch as opposed to roll pants. How do you do it?

    • SB

      Roll an even 1/2″-3/4″ two or three times (depending on the height you want), them simply scrunch it up and slightly unroll the inside, so it doesn’t look so perfect. Don’t over-think this! It’s supposed to look haphazard. Hope this helps, Dan

      • Anonymous

        Man i love what your doing bra!

  • The Shoe Snob

    Lucky that there is still warmth in NY, here in England it already feels like winter!! Love the idea of your looks, layering is my favorite pastime. Although I am not so sure about having two button-up on’s, for me it is a little bit aesthetically strange but I am more for giving props for doing something that no one else does then saying that you shouldn’t do it. Keep up the good work, always a pleasure to see what kind of outfits you have conjured up!

  • Anonymous

    Not a big fan of the last two looks, but I really like the first one. It looks so rugged with the western shirt, jeans, and desert boots, but then suddenly out of nowhere, it’s like BAM! A bowtie!! It’s a very unique look.

    • SB

      A little high/low, formal/casual contrast is usually an easy way to create a look that is visually interesting. Thx for reading. -Dan