Fashion Makes Fools of us All

April 1st, 2014

Share on FacebookTweet about this on TwitterShare on Google+Pin on PinterestEmail this to someone

Style is not something you are born with.

I believe it is purely nurture over nature. It’s learned by observing others. Whether it be your father, your friend, or your favorite style blogger. Like any other skill, dressing well and developing good personal style takes practice.

It’s a journey. And like every journey, there’s ups and downs. We test our limits. We win some. We lose some. We try too hard, then scale it back. When I started writing about style five years ago (in March 2009) I was still a college basketball player who grew up on a farm. I didn’t know much about clothes. I knew they could make you cool. I knew they were an important part of a person’s  identity. And expensive ones could be scored on eBay at a surprising discount.

So over the years naturally I’ve had my share of “what was I thinking?” moments. We’ve all had them. Like this one, for example:


Cheap fused suit, tacky floral shirt, “sword” tie bar, silk knit lapel accent, floral pocket square with button detail, red leather bracelet…it’s all just way too much. I would never wear something like that now. But you live and you learn.

If you’re reading TSBmen, chances are you’ve been developing your personal style as well, and you’ve probably tried some new things along the way. So what were some of your “I can’t believe I wore that” moments?

In the lighthearted spirit of April Fools, feel free to share in the comments below.


Hope somebody pranks you today.

Yours in style,


Share on FacebookTweet about this on TwitterShare on Google+Pin on PinterestEmail this to someone
  • James Franco

    I actually like that look, Dan. You might could scale back on the accessories, but a sharp look, nonetheless.

  • L.A.B.

    My downfall was skinny jeans. I played soccer my whole life and lifted weights. I was obsessed with skinny jeans. My pants were just so tight. What was I thinking? I cannot wear skinny jeans without looking truly out of proportion. Live and learn.

  • Al Bizzy

    I think the Thom Browne influence really jacked me up for a second. Although I still wear my trousers with no break; I used to have my pants hemmed above the ankle. My jacket length was pretty severe too. I remember the body of my blazers ending at the same point as my sleeves. “What the hell was I thinking?”

  • Unseen Flirtations

    This is like an AA meeting.

    My name is Unseen Flirtations and I used to wear 3 button suits. I used to not understand 2 button suits. I’m not sure what was going in my confused 20 something year old head.

    Also, my previous aversion to wider ties. For about two years, I was convinced that slim and skinny ties were the only ties acceptable to wear. How naive. Ties of all widths serve a purpose, and skinny skinny ties I now realise are horrid.

    Thanks for listening.

  • Changingman

    Ever since following TSB for the past year or so, I can honestly say I havent gone overboard. My faux pas exist in my pre-tsb days. Way too baggy Tommy Hilfiger pleated dockers. Size 16 1/2 , regular/classic fit button ups. I now wear 15 1/2 slim fit/ fitted only. Pretty much over sized everything. Part of it is Im skinny, so lots of things fit be baggy, it was never intentional. I just learned to shop around more and try new things. And found myself a decent tailor.
    Just the other day a lady at work was complimenting my pants/ shirt combo one morning. And then she looked down at my shoes and she just lost it. She went from , “oh you look nice today” to ” oh my god , I love your shoes too!!!!”

    So thank you Dan, Wes, Alex, Towni. Not to mention the special featured guests, and fellow commenters.

  • Nick A

    I don’t think grooming should be left out of this conversation, Dan. There was a point in my college soccer career that i had beautiful flowing locks reminiscent of a young Andrea Pirlo (look it up). After a night of Fireball and memories, I decided I could no longer bare the thought of my hair falling in my eyes any longer. So, jumping at the chance to butcher me, my best friend agreed to give me a late night haircut. About 3 minutes and 12 inches of hair later I was bald. Old man bald. I woke up in the morning and could literally feel the infrared light pulsating on my virgin skin. Needless to say, that was the ugliest I have ever been. Some men just don’t have the head for it. So remember, as with tattoos, never drink and cut your hair.

    • Daniel

      I disagree. While I think there’s value in taking pride in one’s appearance (hey, I’m on this site), it’s worth remembering that looks aren’t everything. The humility and sense of perspective that can be gained from something as impermanent as shaving one’s head – especially Pirlo hair – is worth it. I shaved my head last year for that reason, knowing that it probably wouldn’t suit me. It didn’t, and I grew back my hair, but I’m glad that I shaved it.

      All seriousness aside, Pirlo’s beard > Pirlo’s hair.

      • Gazman

        If you can pass a football like Pirlo you can wear your hair anyway you like. He’ll still be killing them at 40.

  • ChrisD

    I agree completely, ongoing learning process and “learned by observing others”. And it’s free learning.. just walk around outside if you live in a city and decide what you like/don’t like about others’ outfits (without judging the person!).

    I was (and still am) obsessed with pant-cuff-to-shoe-length ratio. Sized down on jeans so much to get the perfect cuff that I couldn’t bend over in them! And while sneakers may have looked in proportion, boots ended up looking like clown shoes :)

    Took me 3-4 pricey pairs of raw denim to figure out the expectations of shrink & stretch, but now I’ve got a pair that fits like it was made for me whether it be paired with a t-shirt or tailored jacket, slip-ons or work boots.

    I also really dig the pattern in the shirt above heh..

  • Geezer

    Fit, as many have said, and looking like Nantucket threw up on me — real costume sh*t. I am slowly learning moderation and my own style, but I am not yet immune to ‘the winds of change’.

  • Maher S. Hoque

    Shiny shirts… used to love them in my clubbing days. A dark blue shirt with glow-in-the-dark lightning strikes. The much-too shiny red shirt, the faux leather bell-bottom pants. Good lawd what was I thinking!

    And the other posters are right – when I started thinking about fit, I conflated it with tight. I do like the watch in that picture though.

  • Miguel

    Well, when I started reading your blog and others I started doing the same thing, probably over dressing, specially in those areas, too many accessories, either the pocket square (loud ones), the bracelets but what I learned along the way is that less most of the times is better.

  • MS

    A wise man once said:

    “A trend starts. Trendsters get wind of this new ‘tailored’ look and, in what seems like a natural progression, bring it to the next level…and stylish begins to look a whole lot like corny. A trend dies—some men go down with it.”

    I prefer to always stay one half step behind the trends. The fringes, or the vanguard, depending on your position, is where sartorial becomes FASHION. When I first started paying attention to clothing, I got super into DBs, this was in the early aughts now. Bought a whole wardrobe of fitted, short, Thom Browne-esque DB suits. Spent a fortune on tailoring. Than one button, slim, single breasted suits came back in a big way and I sold all my DBs. Now, I could start wearing them again because they’re back! Unless you’re the kind of dude who has a walk-in closet (which I am not), I just don’t have the money or the fortitude to go “all in” on trends anymore. I do me, I do classic, I do minimal. No one’s stopping me for street style shoots or anything, but at least I don’t have to feel that pang of regret when I know a trend that I bought into hard just died, and it’s time for a new line of suits!

    • Aboud

      Words of wisdom Indeed…

  • Jeanscuffed

    I was honestly looking for more fashion faux-pas from your beginning days in menswear in this article. I was especially looking for the cover photo lol. After transitioning into clothes that “fit” at the time and trying to present a better image, I do remember tucking in my sweaters when I wore a sweater/dress shirt/tie combo. It felt natural at the time but it didn’t look believable if that makes sense. I looked stiff in my clothes. Looking back it was like, “Why did I wear it that way??” I still have a long way to go seems like. I just hope in the next 10 years I won’t look back and wonder why I wore things like I did.

  • cuponoodles


    I could not disagree more. That is one of my favorite looks from one of my favorite all-time posts. The shirt in particular I’m a huge fan of, and while it does break the “no more than 2/3 rule” (lapel/pocket square/tie bar), I still love it.

    • Dan Trepanier

      Hah. That’s the beauty of style; it’s all subjective and based on opinion.

      • Jakob

        Which post is that?

  • Guest

    checkered black/dark grey shirt with dark blue floral scarf.

    Bad color combination, bad pattern combination overall a lousy look.

    • Dan Trepanier

      That doesn’t sounds great, lol.

      Thx for sharing!

  • Anon

    I could be mistaken, so my apologies if so, but is that not the suit from your namesake line?

    • Dan Trepanier

      Good eye! This particular suit was actually a sample garment we used to test the fit for the collection – so it’s missing most of the internal construction – there’s not even pockets on the inside. I was just so excited, I had to wear it anyway :)


    • Tom

      LOL! It is

  • Nick

    When I first got into menswear I became obsessed with fit. A lot of places, like TSBmen, emphasized fit, usually by posting horrible pictures of baggy clothes. To avoid it I started sizing down in almost everything, but in retrospect, it’s quite clear that I went too far. I wore a lot of shirts with pulling around the chest buttons etc. I eventually learned to size up again – by finding the right fit AND the right size. Nowadays lots of brands have slimmed their garments as well, so I don’t think baggy fits is as much of a problem now, as, say, 5 years ago.

    • Dan Trepanier

      Thanks for sharing Nick. I think we’ve all gone through this. With the “slim fit” craze, a lot of things became “tight”. I see it all the time even now, but I think guys are learning about balance and subtlety.

  • TO

    When I first started wearing ‘more tailored’ clothes instead of the ‘normal’ baggy fit at the time, I am sure I wore my fair share of tight clothing.

    Not completely my fault at the time b/c it was due a lot to my abnormally big thighs and seat, but I didn’t really know how to accommodate for this then. I can remember in particular doing a simple jeans and tshirt combination that looking back probably looked painted on.

    • Dan Trepanier

      Ye ‘ol thunder thigh syndrome. The athletes in the crowd can certainly sympathize.

      Hope the new gig is going well TO!

      • TO

        Haha, yep.
        Better than you can imagine. DJ and Frans are great guys!!