TSB’s 5 Most “Controversial” Looks

September 24th, 2013

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Menswear is a high-risk/high-reward kind of game.

The trick is balancing the traditional culture with innovative ideas.

Statistically speaking, the posts that perform best on TSBmen are those that are more experimental, but we try very hard to balance those with more informative articles.

But risk-taking is part of it. After all, stepping out of your comfort zone is the only way to get better, at anything.

That said, our primary goal is to inspire guys to be a little more creative in their dress and develop their own personal style. So the team and I compiled the 5 most “controversial” looks that we’ve ever published on TSBmen. If nothing else, they prove that when you take a fashion risk some people are going to love it, and some people are going to hate it. Ultimately, though, most of those people will respect that you had the balls to try it.

Be sure to check the comments on some of these old posts…


5. Flannel Pajama Layering


From “Unexpected Layering Part II

4. “Grandma” Floppy Hat


From “1 Piece/3 Ways: Chunky Belted Cardigan

3. Shirtless Cardigan


From a response to “the haters” back in the day.

2. Women’s Blouse


From “Borrowing from Her Closet

1. Removable Fur Collar

016 copy

From “Innovative Accessories: The Removable Fur Collar




Do you take fashion risks?

Does it pay-off? Or backfire?

Share your experiences with us in the comments below!




Thanks, as always, for reading.

Yours in style,


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  • Javier H.

    Grandma Floppy Hat. First thing that comes to mind when I see that look is a “scarecrow”. Definitely not your style Dan!!!!

  • http://www.stunodpictures.com Jason P.

    I see the fur collar and the Thrift Shop song pops up in my head.

  • http://www.stunodpictures.com Jason P.

    I did the shirtless cardigan and flannel PJ layering look. I don’t think I could personally pull off the former but I am going to try the latter for sure! Though right now with temps in PA set to get to 80° this week, it’s not yet time for the fall getups.

    Speaking of fall, any chance of posting some stylish and inexpensive fall jackets to look at?

  • Brent Kuz

    PJ top is pretty cool. The rest is avoid like the plague

    • http://tsbmen.com Dan Trepanier

      Don’t miss the point.

  • Khalid

    Somewhere in Canada, Don Cherry is looking at this page and saying “That’s my boy!”

    • http://tsbmen.com Dan Trepanier

      hahahaha. I remember writing a Don Cherry vs Craig Sager post back in the day…

  • Kevin F.

    #5 Using the Pajamas as your top layer is pretty chill/casual for the fall season. Time to test this out.

  • Kevin

    Most of those are pretty questionable, but I thought the pajama look was actually a really cool example of taking a second look at your wardrobe and coming up with unique looks.

  • http://vimeo.com/edgarmorales Edgar Morales

    Really liked the first 2;

  • Gazman

    Thanks for the post. Was funny.

  • Sergio

    This is why though Dan and the team, why you guys inspire the style of other men and not just merely have people follow or try to mimic what you guys wear. Always pushing, stay at it!

  • Stevesy

    “What, you don’t like my pajamas? Well I don’t like your corporate slave uniform!”

    Bored to Death, anyone? A show with its fair share of #menswear moments

  • http://eightgiants.com Josh

    It’s funny that the most controversial look was the detachable fur collar, cause I found one last winter, got experimental and took a chance with a look that got me in your other controversial February Giveaway!
    If it wasn’t for that ‘edgy’ post I wouldn’t have thought to rock the fur collar. On top of that I found the fur collar in the woman’s section of an antique shop with a girl I was dating. She thought I was crazy too, until she saw me in it and agreed that it worked.

    So I think you guys are doing a fantastic job of getting others riled up to stretch out a bit from the ‘novice’ or ‘safe’ looks from time to time. On that note, I’m taking that PJ top look for the fall and making it my own haha.

    Not everything will be for me, but there’s certainly no end of inspiration I get from here.


    • Chasin

      I was really inspired by the fur collar too and I did the same thing. I went to an antique store and bought it from the women’s section. I liked it so much that I bought another collar from a different store. So no I have 2 fur collars and love them both. I actually liked all of these “controversial” looks, especially the blouse. I have no problem shopping in the women’s department if the fit and look are right.

    • http://undefined TimL

      Great post!

  • John B

    The point of this site is to inspire. While I wouldn’t try many of these looks, the point is to start thinking outside the box! The text on the fur collar post is missing though (on the denim jacket look at least)!

  • Nicholas

    I actually like all of these looks for different reasons… aside from the gladiator sandals. :)

  • A

    Half of those links are broken.

    • http://tsbmen.com Dan Trepanier

      The two broken links are now fixed. Apologies.

  • Shawn

    Love the black watch PJ top, almost looks like a work shirt. And I wish I had that removable fur collar, very in-your-face, that whole look looks good to me! Never liked the floppy hat trend that was trendy in Pitti Uomo last year, and the woman blouse is… different!

  • Carlos L

    A few links on here are broken.

    That fur collar…. YIKES! LOL

  • cam

    link to belted cardigan post is showing an error

  • Gary-A

    Put This On just recently raised a similar discussion. Basically, it came down to needing to know the rules before you break them.

    The TSB team clearly knows the rules. Myself, I tried to be too adventurous at the outset of my style game. Now I’ve pulled back and am focusing on nailing the foundations before jumping back into the deep end.

  • Dustin

    Love it! I love that TSB throws in the occasional “experiment.” Fashion would be boring without pushing boundaries and trying new things. Not every experiment ends up working, but it’s always fun and fascinating.

  • Danilo

    Cool post. I like the flannel pajama look.

  • Austin G


    I am hoping for some guidance here, I am interested in getting a big chunky belted cardigan pretty much exactly like the one in picture 2 of this post. Could you guys either point me in the direction of where to look for one or help me locate one? Thank you.

    • Austin G

      I meant picture 4. Sorry!

    • John B

      I’m quite sure Michael Bastian made one for his previous two collections. I also remember Dan wearing a vintage one at some point. I’ve also seeen some on women’s stores, although that could be akward!

      • Austin G