“Timelessness”: Classic Cool or Basic Boring?

March 3rd, 2014

This weekend I fell into an interesting conversation about the boom of traditional menswear and the resurgence of classicism among young men. It’s no secret that our fashion-conscious generation appreciates tailored suits, wears classic felt hats, and understands the long-lasting value of old world things like goodyear welted shoes.

That said, there exists an interesting dichotomy in modern men’s style. On one hand, guys want to use personal style to express their individuality and show the world their true colors. On the other hand, guys want to conform and look “timeless”; in such a literal way that if a black & white photograph were taken, it should be impossible to determine its date.

The desire to look timeless, in my opinion, comes from the glamorization of 1950s-era Hollywood icons (guys like James Dean and Steve McQueen), the practicality and economic benefit of investing in pieces that can be worn over a long period of time, and the fear of looking back at old photos and saying: “Damn, what was I thinking?”. This combination causes many men to favor a nondescript uniform of menswear staples that date back to the 1950s; things like oxford cloth shirts, khaki chinos and crewneck sweaters.

But where is the fun in that?!

Personally, I love looking back at old photos and being reminded of a specific time, place, and frame of mind. My style is constantly changing, just as I am, so when I see an old photo (even in the archives of Articles of Style) I usually think “Damn, that was such a different time in my life. I thought differently, acted differently, and of course, dressed differently”.

There was my Allen Iverson period, for example. In ninth grade I wore exclusively baggy streetwear brands like Rocawear, FUBU, and Sean John and even had my hair braided in cornrows… I was nice on the court though, don’t get it twisted. After the cornrows I let my hair out and permed it with tight curlers, going for more of a smooth Michael Jackson/Lionel Richie vibe (and only listening to old school R&B like R.Kelly and the Isley Brothers). Point being, I would never trade those distinct memories and experiences for an everyday oxford cloth button-down and khakis.

On a similar note, as much as I appreciate the classic styling of all-American guys like Paul Newman and Cary Grant, I get much more excited about the polarizing non-conformist styles of icons like Michael Jackson in the 80s, or risk takers like Lapo Elkann. These are men who have used their unique sense of dress to amplify their characters, and in turn, their careers.

As I’ve written before, investing in a classic wardrobe can have you “well-dressed” for any occasion, but personal style can tell you a lot about a person…


So what side of this men’s style dichotomy or you on?


Looking forward to your comments below.


Yours in style,

Dan Trepanier

  • rajith

    I look at this differently. For me it depends on my goals. One of the powerful lessons I learnt through trial and error is how I could use my clothing to support my goals.

    For the most part I dress classically in a muted color palette so I look polished but not necessarily stand out just on the merits of my clothing.

    Other times (few and far apart) I use my clothing to make a statement.
    – I have deliberately gone very casual (not sloppy, still well coordinated in tailored clothing) to some events (meetings/functions) when every one else was wearing a suit & tie.
    – OR wore a suit and tie when every one else was casual.
    – I sometimes wear a bright red sweater when I go for meetings that I
    know I need to fight tooth and nail to get my ideas across. I will grow a beard and ratchet up my aggressiveness to go with the clothing.The in your face clothing is loud and obnoxious, but sometimes it serves the purpose.

    When I use clothing in this manner, sometimes it was a sign of protest, sometimes to show I’m a non conformists and other times to make sure I stand out from the rest.
    It often worked, but sometimes it backfired.

    Btw this seems to suggest that there is some merit to the above http://on.wsj.com/1kZWqSO

  • andres

    Becoming a person moving in different cities. Coming from south america (Colombia), then living in NYC – where I got to know TSB – and now living in Berlin have made me a confident player in any urban game. I am an person that is learning how to activate actors. Thanks a lot.!

  • Daniel Barea

    Have to agree with cam for the bulk of us who don’t desire top hipster status but rather a well thought out, classic, modern accented tailored look that is timeless what may seem boring I look as transcending….I.e the 1953 Porsche. Then. Now. Future. Fresh as ever.

  • Jeremie

    In my opinion, the fact that we even refer to the style as being timeless definitely says something. It means it will never go out style, no? Men in tailored suits will always look good no matter what year it is or what era we live in.

    However, as much as the “timeless style” is well… timeless, personal style comes into play these days. Compared to 50 – 60 years ago, when most men worked in offices and looked forward for that promotion coming next month and all resembled those “Little boxes” from the song with the same name, today we live in a society where thinking freely and expressing yourself is encouraged. Some of us do it through art, or oratory arts, or even blogging, and some of us, like the men (and women?) reading this blog, like to express ourselves with our clothing. I completely agree with you, Dan, when you say that style can tell a lot about a person. I mean, our mothers don’t pick what we wear every morning anymore…. Well I sure hope yours doesn’t. We make those decisions now. And so our style becomes a visual aid or reference to our personality.

    Most of us readers, when seeing a WIWT post from TSB, will like the different outfits for various reasons. And that proves that we all have different personal style. But I do believe that personal style can definitely be inspired by a favourite era (not necessarily the post-WWII era). Personally, I love the 1920’s. I love the fashion, the culture, the music. And so I often will inspire (consciously or not) my outfits from my knowledge of the jazz era.

    So isn’t it just a big vicious circle? Isn’t it our individual style that decides whether we want to be timeless and wear tailored suits with felt hats? Maybe there is no timeless style. Just similar personal style choices.

  • http://www.lucidlingo.com.au/ Gazman

    Interesting question and good post. This is my take. People’s sense of style in clothes change over time, much like our preference in food, art, travel destination etc. It’s an evolutionary process that is aligned with fashion, age, lifestyle and influences (music, film etc). When we are young and impressionable, we tend to be more influenced by role models and by our heroes and what we see around us. As we get older we get to a point where we are more settled in our sense of style. We know what suits us and what doesn’t. Many don’t get to this point.

    Now the debate here on classical/’boring’ versus individual style (supposedly more ‘out there’, brave and audacious) seem to revolve around the notion that individual style is all about being adventurous and radically different. I don’t think this has to be the case. Men don’t have to dress like Wooster or any Luca, Lapo and Lino in order express themselves and showcase their personality. You can still dress classical and express yourself and that’s where accessories come into play. I see this approach on this site all the time. A hat, scarf, textured tie, pocket hankie, patterned blazer etc can lift a classical look into one that looks more dapper and distinctive. The way you combine classical elements and the colors you wear can also transform an otherwise indistinct outfit into one that stands out.

  • VB

    Dude you were never in the 9th Grade…you were in Grade 9

  • Steve

    I think the majority of one’s clothing should be made up of classic clothing otherwise you’ll be buying a new wardrobe every year or so. You should buy a few stylish outfits that will keep you looking current but I think classic is always the way to go.

  • JM

    Some guys create a uniform because they reach a point where they’re comfortable in what they’re wearing and don’t feel the need to change it up. Others keep innovating because they like the challenge of putting together outfits that cause people to stop and analyze them. Neither is better than the other, they’re just different. You just need to figure out where on that spectrum you fall.

  • Charles Edward Fromage

    This post brings up an important issue. In our personal style evolutions we’ve probably taken missteps. That’s part of the journey. That’s partially why preppy style is appealing: Stricter dress codes when growing up deter over-the-top style mistakes. And it’s a more timeless American look – The clothes don’t really change, just the cut and fit (for the more fashion-conscious).

    But for people who didn’t grow up in that environment, the important question we must ask ourselves regarding style, is “Did I stay true to myself?”

    Sometimes trends in style and fashion can be very tempting, and we can get tunnel vision and lose ourselves in the desire to have something current and cool, but as men who have been through it before we can see this tendency in ourselves and learn to abstain.

    We change as people, especially in our formative years, but as long as we stay true to ourselves and our lifestyles there will be no true regret. If cornrows and snap-up warm up pants were what you were really feeling in 8th grade, that’s cool. There will always be idols who push style. It should be a fun thing. But when we look back at it all, we will be most satisfied if we have not relinquished our own ideas of style and what it means to be a well-dressed man.

    From a recent post on “Put This On”

    “Someone once gave me a very fine description of Cary Grant’s attire at a time when the motion-picture star was considered the best dressed man in this country: ‘I’ve been with Cary Grant a dozen times lately, and when I leave him I have the recollection that he was beautifully dressed. But, for the life of me, I can never remember a single thing he was wearing — his hat, shirt, tie, suit, or anything else.’ And that’s what all of us should try to achieve — the impression of being well dressed without wearing any one article that blatantly sticks in a person’s memory.”— Bert Bacharach

  • Pinstripe

    Where does personal style become ‘doesn’t have a clue’? I don’t know, but perhaps a cliche is appropriate here (because it’s true in my opinion): before you can play around, break the mold, and get funky, you need to be able to master the basics. That’s why timelessness is prevalent I believe: everyone should grasp these basics before putting on a neon pink blazer and calling it ‘style’. Kind of like etiquette: you need to know how to behave before you can elegeantly and snarkily misbehave. In that sense, classic cool is the entry level required capability before going off the deep end. Furthermore, it has to do with taking others into account, just like etiquette. Style is non verbal manners, communication. Peacocking is the fashion equivalent of shouting at a funeral. Sure it gets attention, but in bad way. It’s just loud.
    This make any sense?

  • TO

    I personally am skewed more towards the side of trying to be “well dressed” versus purely “personal style”. I tend though to appreciate and try and draw from both sides.

    I am limited by a smaller budget for clothes, and this has been the biggest factor that has driven my creativity when it comes to dressing- because it influences my options/preferences of where to shop, and thus things that I wear, in a way that entices creativity. For example, sometimes I make things work for me and my style from thrift/vintage stores through unconventional alterations, or thinking thinking outside the box in terms of styling, simply because the items are in my opinion awesome (and also cheap!).
    But, the reason I was initially drawn to sites like TSBmen was generally to simply dress “better” and “do it right” because I saw these things as goals. So because of my experiences I get excited about thinking about/practicing both sides of the coin.

    If one tends to pay attention to dressing in general and appreciates any type of expression through dress, which is who I think this discussion is geared towards (not those who never put thought into how they dress and present themselves and generally would benefit in many life areas from simply ‘dressing better’ or with a more ‘classic’ wardrobe- even though this area may not mean anything to them initially) I think it is almost inevitable that they will eventually get a little tired with what they are wearing if it seems to have become pretty static or boring, and will change something, either to simply ‘switch it up’ or to express a genuine mood, feeling, mind-state, love for something (such as the hip-hop/basketball/R&B examples Dan stated), etc.. Dan is at the extreme end of this spectrum, to the benefit of the fans of TSBmen.
    Others, however put as much thought into dressing, but end up satisfied with a specific ‘uniform’ that is in their minds perfect for them, and they represent the other end of the spectrum. I will never get how those people do that, but respect their commitment to dressing ‘optimally’. Of course, a big consideration is always coming back to context, as for example a lawyer can’t show up to court in cords and cricket sweater, no matter how strongly he wants to express that view on dressing, so in a way the side men are/should be on is usually on some level predetermined.

    • TO

      I jumped right into my response to the question posed in this article, before I could state that it is a very well-written article opening up a very interesting discussion!

  • Chris

    Great article. If you could ever get a feature with lapo that would absolutely take this site to a whole new level for me. And it’s already my favorite menswear blog.

    • http://www.TSBmen.com/ Dan Trepanier

      Thanks Chris. Lapo is on our list ;)

  • Howie

    I think this is a fantastic article and discussion. I think the important part is the relationship between self-doubt/confidence and style knowledge. I know when I first started following Dan I was almost embarrassed to wear the new colorful socks I purchased with my everyday khakis and oxford. Now I am confident wearing some items that fall more in the Lapo camp than the JFK camp. I think even as we in the normal working world learn more about first understanding the rules and then becoming well versed enough to start bending or breaking a few, we really start to see the development of personal style. It is a journey. You add just one thing to your wardrobe that is maybe a little “out there” until you gain confidence in it. Then it is time to try just one more. This slow progression is how you develop your personal style. Dan does a fantastic job of giving us all a source of new ideas, or a combination of items you may not have thought of that will give us our one new “out there”. Once again, thanks Dan. You are helping us all go as far as we
    want to go with our style, and you are able to speak to each of our difference on your one site. The past few years have been a blast and I look forward to continuing to learn just one more “out there” idea from you to further develop my style.

  • levijyron

    Oh my god no pictures

    • http://www.TSBmen.com/ Dan Trepanier

      Sacre Bleue!

  • Jaws

    A big part of this discussion is what role clothing plays in a person’s life. A large part of the appeal of icons of years past is the obvious ‘clothing is secondary’ concept that is evident in classic men’s style. The common criticism of fashion forward dress from a classic philosophy is not the ‘risk-taking’ aspect, but the thought that they exert and think to a non-practical degree about clothing – and the classic dresser may see a reflection of their life principles or insecurity in seeing this desire to attract ‘of-the-moment’ attention through fashion forward dress. An image of McQueen, Newman, Arnold Palmer – their most prized images that resonate true style, are images where clothes are irrelevant – it’s where they’re living life with passion and conviction.

    This is one of the major criticisms I have about clothing blogs – which constantly champion themselves as ‘style’ blogs. Some of the most stylish guys I know don’t care about clothes. Style isn’t about clothes; it’s about life and your spin on how to live it – clothes are but a small piece to the overall puzzle. Although clothing has the power to convey identity, it should always be secondary to everything that life has to offer.

    • Sharif

      So you think people should have a limit or something to how much like care about clothes

      • Jaws

        Perspective is essential. ‘Classic cool or basic boring’ is an off premise.

  • Nick A

    Amazing points all around. I think something Dan and co. do brilliantly, that a lot of other content sources don’t is focus on fabric. I think the concept of having a uniform and sticking to it can be phenomenal for certain people, including myself. What Dan has really helped me with is taking a basic, consistent outfit and interjecting different textural notes and color palates into it. Moving from CT to LA a year ago I felt like it was time to get away from pastels every day and experiment with different options. Playing with linen, cashmere and all the other wonderful cloths of the world has allowed me to interject a little individuality into my oxford and jeans work uniform. Thanks again Dan!

    • http://www.TSBmen.com/ Dan Trepanier

      Awesome comment! Thanks Nick. Totally agree. Subtle changes can go a long way, and fabrics are a great way to implement a subtle change to an otherwise familiar look.


  • http://www.anorexicescapades.com/ BougieHippie

    Brilliant post! I think style is and fashion is the perfect scrapbook or time-capsule. I like quality clothing but I do like look over my picture to see how I’ve grown and how times has changed.

    I love going home to my parents and walking through my dad’s closet as see all the awesome things he has collected over the years from the 60 to now. That’s the kind of closet i want to create.


  • http://unseenflirtspoetry.wordpress.com Unseen Flirtations

    Wait, hold on, what? You had cornrows. What? Wait, hold on. What? Wait – what?

    Hold on. What? etc

    • http://www.TSBmen.com/ Dan Trepanier

      Hah. Yup. You wouldn’t believe the spot in Detroit where I got them done.

  • Nick

    This article is indeed some food for thought and also well written. In my opinion the you can never get it wrong with the timelessness look, practicly every event you will go to, a classic look will suffice if it’s nicely fitted. On the otherhand if you like to stand out you should add some twists to a classic look and develop your own sense of style. But before you go there, you should understand the classic pieces and the general “rules” that come with it.
    This is what TSB stands for in my opinion, Dan and the guys are showing us and teaching us about the all time classics and also some nice features with guys who have an impeccable sense of style, via this way us the readers can learn how to develop our own personal style through the path of looking, reading and experiment with all the looks we’ve seen here.

    ps love the new look and way you’re going with the site


  • Zachary Glotfelty

    I’m very much a “classics” person. I have more than my fair share of oxfords, etc. One major difference is that I go more for the heritage or workwear type aesthetic than for, say, classic prep. I think for me, this comes out of a desire to express myself. Take for example a musician (I play guitar for a living so this is about the best analogy I’ll be able to pull together). As a musician, my journey towards self-expression has been helped out by other guitar players. I hear their sounds and the way they play and begin to emulate that. That’s what creates a personal self expression: mixing together influences. So whether that’s with guitar playing or getting dressed, you’re still expressing yourself. I tend to take a lot of influence from Daiki Suzuki, Wooster, Angel, Ralph Lauren, guys like that (can’t exclude Alex though, that kid has influenced my style pretty heavily over the past year or so). Those guys take a lot of risks that I don’t, sure, but I don’t really have the time/money/experience/vision/etc to pull that stuff off. I can’t wear a patchwork seersucker jacket like Wooster can. But I can take cues from that and subtly let that influence my style in some way. Self expression is different for everyone and I can still have a real appreciation for guys who do things outside of my box. Actually the Nick Fouquet post was one of my favorites in recent memory, even though I’m not necessarily influenced by his look, I can still be inspired by it. Maybe that doesn’t make a lot of sense to most, but it works for me. The only thing that REALLY grinds my gears (and maybe I should stay off of Tumblr as these people congregate there) is when guys use menswear as a means to pick up women. They talk about how their style gets them into bed with someone new every night. Womanizing is dumb. Bragging about it is even dumber. It’s 2014.

    • http://www.TSBmen.com/ Dan Trepanier

      Great comment. Thanks for sharing Zach. And I’m sure Alex will be flattered. Alex – where you at?

      As far as the last part of your comment… From my experience the more somebody brags about “womanizing”, the less “womanizing” they are actually doing. Especially if said bragging is done on the internet!

      • Zachary Glotfelty

        Hah! Truth in that.

  • MS

    Really well written article, Dan. I think, as with everything in life, it’s a big tent. That is to say, could never be one or the other. Some people reinforce the classic, the normal, the stable and conventional; some people are natural boundary pushers. The normals will occasionally celebrate, occasionally criticize the boundary pushers, and the boundary pushers will draw influence from, and occasionally criticize as staid the normals. That’s just the nature of the experiment, that’s all.

  • Will

    Let me preface this by saying I’m a fan of the site who typically skips some of your more creative or far-out features.

    I think people who are immersed in the style/fashion industry get bored with conventional or “timeless” looks simply because they’re exposed to this stuff so much more frequently than the rest of us. Familiarity breeds contempt (or boredom), which is why guys like Dan want to push the envelope. I can understand that impulse, but there’s some tension between being creative and expressive and providing worthwhile advice to guys who just want to dress better in less fashion-forward environments. Something to keep in mind when you’re planning future editorials.

    • http://www.TSBmen.com/ Dan Trepanier

      Thanks Will. I agree, but I don’t think we should stop there. Our goal with TSBmen is not so much to say “where this to work” but rather to help guys develop their own sense of style (which extends far beyond clothing). By seeing and understanding other peoples’ unique perspectives (via “far-out features”), we not only learn about style/fashion, but also about the psychology of dressing and what our image says to the outside world (and whether or not that is congruent with our intention).

      What I’m trying to say is, if you stop short and say “this isn’t relevant to me, all I need is an oxford shirt and penny loafs” that can be helpful, but you may be missing out on the true benefits of developing (and appreciating) a unique perspective.

      All that said, we do have some more “practical” content coming up this week.


    • Juan

      I completely agree with Will, and while it may be true, to some extent, that wearing some sort of “uniform” every day might become boring after a while, I completely disagree with some of TSB’s guest’s views on style.

      For example, while I’m not entirely against them, I wouldn’t wear, nor advise somebody else to wear crocs in the winter, simply because you would freeze, and they definitely look better and more natural paired with shorts and a t-shirt, than with a parka.

      The same goes for Jay Gagnon’s cropped blazer+ill-fitting sweatpants+2 inches of exposed ankles/thighs+rugged boots with red laces look. Not only does it break the “fit is everything” rule, which I believe is the only rule that should be followed at all costs, but it’s also the perfect example of what I like to call “fashion over everything”, which is sadly where menswear is headed these days.

      Fashion and style are mutual, meaning they must at all times feed off each other. But that doesn’t mean ill-fitting clothes or pairing a pair of sandals with a hawaiian shirt and an orange snow cape is stylish just because no one’s done it before. Nor that wearing certain pieces is ever okay: a gold-colored pair of shoes will always be a gold-colored pair shoes, it doesn’t matter that they’re Zanotti and were featured on runways in Milan and Paris, they will always make you look like a clown.

      There are so many things that can be personalized and styled in countless different ways within a classic gentlema’s outfit, and you guys have demonstrated this SO WELL over these past few years. Lapel width, jacket length, shirt patterns, fabric choices, accessories, the possibilities are countless.
      I have never seen Dan wear an outfit I wouldn’t wear and I think it’s because he understands “classic with a twist” perfectly. THIS is the direction to follow, in my opinion.

  • Day Shapiro

    Interesting artcle and something that is very relevant. With this most recent menswear revolution as blazers, shoes and all other garments are getting pretty crazy (colors. fabrics, fits) on one side of the spectrum you are by nature going to have people go to the complete opposite side of the spectrum, which in this case is classic. Neither is correct or better, it depends on the person and as Dan touched on, where that person is at in their life. However, I think the most important thing to remeber is, is not how contemporary or classic you should dress, but to ensure that when you walk into a room that people don’t remember just the suit on the man (not always true, some suits are that fly), but rather the man in the suit.

    • http://www.TSBmen.com/ Dan Trepanier

      I agree. The man ultimately makes the clothes.

      Although, like you said, sometimes the clothes can be remembered, even if the man was forgettable…

  • Miguel

    I tried to mix it up both classic and my own style.
    What I do is take tips from this blog and other websites I visit, I tried to match from the different looks to what works better for me understanding that not everything is going to work for me.

    The only thing that I don’t hold back is on shoes and Blazers, I think those two pieces can take you a long way.

  • Owen

    Good post! I totally agree with your point of view (Steve McQueen is my hero), and I also think the resurgence of traditional menswear is because it’s harder to make a complete tool of yourself if you stick to the classics. If you can buy clothes that are the correct size, classic menswear is a safe way to dress. I think once a guy hits 30 he becomes conscious of dressing in a manner that looks too young for his appearance, the result of which is looking like hes having some sort of a pre-mid life crisis. It takes a certain personal style, a knowledge of the rules of menswear and an eye for detail that lets an older gent follow fashion trends without looking too ‘try hard’.

    I fear that the current popularity of traditional menswear might lead to a generation of uninspired (but well dressed) chaps who are obsessed with the conservative and practical rules of tailoring. I agree we should all experiment a little more and have some fun!

    PS – Lapo Elkin? The link is correct by maybe your spell checker changed it.

    • http://www.TSBmen.com/ Dan Trepanier

      Thx Owen. You said something very interesting here: “harder to make a complete tool of yourself if you stick to the classics”.

      This suggests a self-doubt and fear that governs the way men dress, which I think is very relevant and important, especially in these fast changing times.

      My follow-up question then is: as men learn more about the nuances of style, will they move away from classicism and start to develop a more personal approach? As their confidence and experience with clothing grows, do they become less afraid of “looking like a tool” and therefore less traditional?

      So does it all come back to knowledge and experience, then?

      • Owen

        I think even guys who are confident with their style appreciate and possibly seek a certain amount of approval from their peers. Self doubt and fear are definitely a big influence on how we dress – after all there are literally hundreds of style advice websites for guys (but only a handful of good ones, might I add).

        Yes I think it does come down to knowledge and experience. Like you have always said, you have to know the rules before you can break them. I find it hard to believe that some guys are naturally stylish, and simply choose the right clothes, without having a wider knowledge of menswear rules. I think style becomes effortless when those rules become almost subconscious.

        I’ll be honest, I found it hard to relate to some of your recent articles, however I think I’m beginning to understand where you are going with all this. From day one TSB has taught us the basics in easy to swallow lumps. Now you are challenging (inspiring?) us with diversity to encourage us to develop a personal style. It’s interesting stuff and I feel lucky to be along for the journey.


  • cam

    I think the biggest issue here is lifestyle. Dan started this blog while at Columbia and his style definetly reflected this. He was a farm boy with hip hop influences now in the big city and on a campus with American prep influences. That style is largely what people think of traditional American style. OCBDs, chinos, loafers, blazers and the like. It’s what all the basic style write ups suggest for us in America to “fit in” and “look good”. The American Dream (see Ralph level). This was also true for TheStyleBlogger and Dan has done an excellent job forming the basis of this for his readers. Is it boring? After awhile of course which is why Dan’s own style has evolved so much. But it works for his lifestyle because of his profession. People expect him to push style boundaries but that just doesn’t work for most of us. My style goal is simple. I want to enter a room and everyone to not give a second thought to my look. That, to me, means I look nice but not in a flashy way. I had a guy from my office about a month ago say to me “you know, you always look so well put together and it seems so effortless”. One of the best compliments I’ve ever received.

    • Ali Naaseh

      Right there with you, Cam – standing out in a flashy way is my nightmare. Entering a room and having someone think twice about what I’m wearing is the complete opposite of my goal. I’ve never been told I look effortless (which, you’re right, is the ultimate compliment), but I did have a girl see my closet for the first time a while back and say: “you don’t have very many clothes, but every time I see you it looks like you’re wearing something new.”

      As far as looking back on the past goes, Dan, I’m glad you can take it with a sense of humor. I hate remembering the high-school-era version of myself!

      • http://www.TSBmen.com/ Dan Trepanier

        Another great compliment! You guys really get it.

        I mean, people doubted and made fun of me back then, for sure. But in my head, I was always “doing me” and “killing it”. It’s an internal confidence that I think I’ve always had. Some people might call it arrogance – it’s a fine line.

    • http://www.TSBmen.com/ Dan Trepanier

      Well said, as usual, Cam.

      I agree, I’m in a position to push the boundaries more than most. And your style clearly achieves the results you’re looking for (which is the goal).

      The larger question, I think, is even if we aren’t looking to change or update our personal look to achieve different results, does learning about style help us deal with other people’s perspectives, and thus expectations?

      Just some food for thought.

    • LouCaves

      Well put cam. I’ll comment once every three features but read all of them and most of the comments too. Your comments are always fair and objective.

      Although I am not a fan of “fashion” (read: Dwayne Wade in knickers or a scarf in 80 degree weather at the ESPYs), I do enjoy seeing a gent with style and owning it. I agree with having to find your own look or reinventing yourself but I don’t want people to look at me and think, “Whaaat?!” With this current wave of interest in men’s style, it seems men in the public-eye dress to score a double-take even when they’re visibly uncomfortable; that’s straight-up peacocking.

      What I take from Dan’s commentary is this: whether it’s going from corn-rows to product-shaped hair or sports jerseys to bespoke shirts, this is a process. Be confident during your own process.

      I used to enjoy no-tie Fridays.But since I’ve become a reader of TSB (little over 2 years) I wear ties to work even when the office dress code doesn’t call for one. That approach is because of Dan and TSB rule #1, always bring your ‘A’ game.

      Thanks, TSB.

    • Obie


  • Calvin McCoy

    I could always see your urban hip hop influences, but I would have never taken you for a smooth r&b cat! Haha great post. It’s hard to say which side I’m on. I love the classics they’ll always look great and it’s safe, but there’s something about taking something that won’t work with most people and owning it.

    • http://www.TSBmen.com/ Dan Trepanier


      And hell yea. My 90s R&B collection is EXTENSIVE.

      • Zachary Glotfelty

        I’ve never been much of an R&B guy, but 90s era Brian McKnight and D’Angelo are pretty damn special.

  • Daniel Moretz

    Another great article! As of recent times, I’ve been on a classic creative side of menswear fashion. I appreciate quality made products that are classic staples but have a unique modern (Italian and American) edge. (Tailored Suits, Di Bianco’s, Frank Clegg, Subtle and Bold Patterned shirts as well as classic oxford cloth varieties) I find that it reflects my lifestyle as well. I would rather purchase one item of quality that will last and get better with age than ten poorly made/designed items that will degrade rapidly. That’s probably part of why this is one in a select few blogs I can relate to as we have a similar philosophy when it comes to making a purchase.

    • http://www.TSBmen.com/ Dan Trepanier

      Quality over quantity brother. Don’t shop, invest.