Style Upgrade: Mike Cannon

August 6th, 2013

Mike Cannon is a 23 year-old actor and musician who currently works for a tech startup in Brooklyn, as an account manager for a new mobile marketing app. He just got a promotion at work, so now felt like a good time to try to upgrade his look.

“I always knew that fashion was important to the way you’re perceived – I mean, I was an art student in New York City – but it felt really cost prohibitive to keep up with the stylish crowds in NYC. The problem seemed so daunting that I ended up sticking with the standard jeans and a t-shirt. I was bartending for a while, which got me stuck in a rut because the bar had these uniform shirts for us, so I didn’t really need to think about what I wore for the majority of the time…”

Last week we visited Mike in Williamsburg to check out his current wardrobe and see if we could offer some advice on looking more professional, now that he’s climbing the corporate ladder.

Here’s his transformation.

    Business Casual – Before


    What we can learn from Mike’s “before” look:

    • Buying a vintage jacket is a great way to save some coin, but the fundamentals have to be on point (a tailor can’t fix everything). Avoid anything that is too wide across the shoulders or that has beefy 80’s shoulder padding – or you’ll look like Lurch above. Also stay away from low-hanging lapels that are cut short by a high button stance. A longer lapel line is (higher gorge with lower stance) will always be more flattering.
    • Not all shirts are meant for ties, or jackets. This weak-collared washed shirt above, for example, is not designed to stand up under a tailored jacket.
    • If you’re wearing a jacket, always tuck your shirt in. Same rule applies if you’re wearing a tie.
    • Nothing makes a man look like he’s got his sh-t together better than a clean haircut and sharp grooming. We gave Mike the ultimate summer cut – cropped short on the sides, faded up gradually, and subtly swept back with some light product. Like me, he feels a little too baby-faced with a clean shave, so we left him a very light, clean beard.

    Business Casual – After

    49 2

    “It’s amazing how quickly my confidence was boosted by dressing better.  The second I put on a fitted jacket, I was blown away by how secure I felt. I looked good, and I knew it; that’s a very powerful feeling.”

    Weekend – Before


    What we can learn from Mike’s “before” look:

    • Lose the graphic tees. They’re anti-versatile.
    • There are knits made for summer layering, so you don’t have to use a short-sleeve bowling shirt to ad depth to your look. The linen/silk cardigan below, for example, is designed to breathe and stay cool in warm weather.
    • Swapping shorts for linen trousers = major gentleman upgrade.

    Weekend – After

    45 2

    “The most important thing I learned from this experience can be summed up in two words: fit and versatility.  You don’t have to break the bank to look great. If your clothes fit really well, it only LOOKS like you spent a fortune on them. And when it comes to building a wardrobe, pieces that you can dress-up or dress-down for various occasions are a great value…”

    Business – Before


    What we can learn from Mike’s “before” look:

    • A black pinstripe suit is good for nothing.
    • Mike is fair skinned with light hair, so greys and blacks really wash him out. Notice how the rich navy suit and brown accessories below flatter his skin tone and give him a glow (almost like he got a tan overnight).
    • Again, an unnaturally high three-button stance. Combined with the boxy fit of this suit Mike looks heavier, and sloppier, than he really is.
    • Vintage ties can be really cool, but chose carefully. Some of those funky abstract graphic ties from back in the day are just straight ugly.
    • Look for shoes with a natural toe shape and don’t forget the shine. Notice how much sharper and in-charge his feet look below.

    Business – After


    “People say ‘don’t judge a book by its cover’, but that doesn’t stop people from judging the cover.  Almost unconsciously, [after my transformation] people at work and in my daily life have been treating me like an older, more responsible adult – asking my advice or opinion on things, asking me for directions… Suddenly I’m treated by my superiors at work more as a peer than as a younger person in the office.”

    Thanks, as always, for reading. Special thanks to Mike for being such a good sport, and to Suit Supply and Ted Baker for sponsoring product.

    Yours in style,

    Dan Trepanier


    Styling by Dan Trepanier. Photography by Alex Crawford.

    • http://undefined Jay J

      I know this suit is from Suit Supply.However, can you provide the exact suit from the website? Model etc.

      Thanks! And good job!

    • Edwin C.

      Im so happy I took a second look at this post. If I’m not mistaken, that is the Washington suit from SS, right? I ask because I’m looking to make my first purchase from SS later this week. Only issue is i live in South FL and im a little worries about making the purchase online. Any comments/advice on their fit? I usually wear a “Slim Cut” 40.

    • Nathan Wind

      The absolute best upgrade ever. The T-shirt/Charlie Sheen bowling shirt combo in look 2 had to be a “ringer” to make the upgrade look even more incredible, right? KUTGW.

    • matt

      This was probably the best before/after I’ve seen on the site. I literally could not recognize the dude from the top and bottom picture. Non-verbal cues are 85% of communication and this transformation puts him light years ahead of the competition. This post embodies the soul of Good job and keep it up.

    • Rum

      Although I get your attempt, unfortunately this isn’t cool. Giving him the cropped sides cut, menswear getup – the world of menswear isn’t about makeovers. Shit’s just annoying. Tell the guy where to learn about menswear, and he’ll find what appeals to him. That’s what personal style is – not ta-dah!/makerover looks.

    • Wes

      This post was fantastic! You guys need to do more of these!

    • Joe

      I really like this transformation and more importantly the whole idea (though in look two, take off the bowling shirt, swap the high tops for low tops and it’s not a bad look for the weekend). I always joked with my wife that she should buy some ugly clothes and then try to get on a TV make over for the free swag. I think the idea of a “What not to wear” geared toward young men is a great idea (I could have been a “before” before reading this blog, but I’ve definitely made some strides – which would be a good idea for a post or contest, before and after shoots of finding Best of luck on your new projects. Can’t wait to see them.

    • Mondgoloid

      One of the most dramatic make-overs by far….can’t believe its the same dude. Dud to stud for real (no H-mo!)

    • Pawel

      Hi Dan

      I didn’t know where to put it, but I wanted you to see how lame our Polish fashion bloggers are. Here you have an exmaple :

      • Steve

        This kind of style does not really scream manly. Looks a bit metrosexual isn’t it?

    • TO

      Have to bring light to the NBA Draft “Upgrade” that has been going on for the past 10 years! How things change:) Check out this image:

    • Sosa

      It will be awesome you guys moving down to L.A.. now I can drop by for a visit to the space as one of your avid readers and maybe play some ball.. of course if you still hoop! Awesome post too!

    • Samantha

      I would agree that he looks better than before, but I think some of the changes took him a bit too far away from his original sense of style and he looks kind of douchey and pretentious now. As a girl, I would much rather go for the funky guy in the cut-off shorts than the pretentious-looking guy wearing linen trousers because someone told him to.

      • Dan Trepanier

        Great comment! The hope is that he takes this new framework and puts his own personal spin on it over time… I agree, it defeats the purpose if he can’t look and feel like himself…

        Thanks for sharing Samantha!

        • Samantha

          Would love to see an update on how he’s incorporated his new pieces and expertise in a few months!

    • http://undefined Nate

      What a transformation! The guy looks like a model now! Just goes to show what on-point fit, versatile pieces, and good grooming can do for your image.

      I would wear everyone of these looks. Bravo chaps.

      • Dan Trepanier

        Thanks Nate!

    • Jos Kelly

      I need to show this to a whole bunch of my friends. Brilliant.

      • Dan Trepanier

        Please do :)

    • BF

      Seriously dan, you guys should do more upgrades..
      Maybe have your readers submit boyfriends etc who need style help…

      • Dan Trepanier

        We have a new strategy to do them regularly in LA. This type of content will likely become a larger part of TSB’s future.


        • BF

          It’s excellence .

        • TO


    • Bob P

      That third look is astoundingly awesome. Love that navy suit.

    • http://undefined Steve B.

      I read the blog regularly, but this is my first time posting a comment… because this transformation is amazing!!! Keep up the good work guys and good luck on the west coast.

      • Dan Trepanier

        Thanks Steve! We hope you’ll comment more often. Along with the new site upgrades will be a whole new discussion system, to allow our community to communicate better…

    • TO

      My favorite upgrade you guys have done so far.

      Each time I scroll through the upgrades I am so eager to see the transformations.
      It is one thing to see individuals who are versed in style pull off stylish looks again and again- eventually some of the appeal gets taken for granted. But it is such a special moment to see the image of an individual change with a new approach to their dress.

      Gotta know, where is the belt from? Great work gentlemen.

      • Dan Trepanier

        Thanks TO! I don’t know, your pops’ upgrade was pretty epic!

        I also really enjoyed the first makeover with our CTO Gabe:

        Belt is from Suit Supply. When you coming to play some ball and hit the beach in Cali??

        • TO

          Thanks my man! All the upgrades have been great.

          Nice- love that belt.

          I may have to escape the Canadian winter down there for a bit!

          I hope you got my message with the info about my friend down in LA:)

    • Khoa

      Wow, whoever said clothes don’t make the man need to see this. This is a classic case of 13 going on 30, I must say. However, did he seriously dress like the “before” all the time or he just pulled out all the skeletons in this closet specifically for this shoot? I really am wondering.

      • Brent Kuz

        I agree I haven’t seen something as bad as before look 2 in a long time. Looks 16yo. Although the belt and chucks can be saved.

        • BF

          I lived in Colorado for 2 years of work and that look spanned the ages of 16-60

        • Dan Trepanier

          The mustang seatbelt belt getting some love! haha

          • Mike

            Told you!

      • Dan Trepanier

        Hahaha – if it’s in his wardrobe, it’s fair game!

    • Jakob

      These posts are your greatest work. Really ambitious and I think they’re the most practical posts.

      • Dan Trepanier

        Hmmm… Perhaps we should do them more often

    • Matt M

      Wow, best transformation I’ve seen on here. Great job guys!! Also, great selection of clothes for each outfit. Love it!

      • Dan Trepanier

        Thanks Matt!

    • MN

      Suit Supply provides great value for the money (aside from their shoes which are poorly constructed).

      I wish SS would lower their button stances tho ;/

      1st and 3rd transformations were nice – 2nd looked a little douchey to me.

    • http://ramblingsofawould-berenaissanceman.blogspot Joseph

      So much of the difference here is due to the haircut too. I have this tendency to go overlong before I get a haircut and everytime I finally do it I think Holy crap that looks so much better! I’m never waiting this long again! Inevitably…

      One thing though, is the casual look really an equal pairing? I feel like I’ve seen plenty of looks pulled off by the TSB guys that are the “upgraded” version of the casual look but this one seems to lack a certain versatility that “weekend runaround” clothes typically need.

      • Dan Trepanier

        We tried to keep the open grey layer and strong belt…but you’re right, we could have done something more congruent. We were a bit limited with time and product…didn’t have access to things like shorts, tees, sneakers, etc.

        Thanks for reading.

    • JT Evans

      Great job, I really enjoyed seeing his transformation. What would be cool though, is if you were able to incorporate one or two pieces from his before looks into his after looks. It might be nice to show readers how to work with/around pieces in an already existing wardrobe. This especially for folks who cannot afford a new wardrobe and/or do not have the resources to find inexpensive vintage and thrifted pieces. In particular, I’m thinking about look #2: I think the shoes would have translated well to a “weekend run around” look and perhaps been a bit more authentic to Mike’s personality and lifestyle. I’m sure sartorially the belt is probably not a winner for some but I think (maybe Mike would agree) that it’s kick ass. With the right shirt tucked into the right pants held up by that belt any dude would look kick ass and unlike every other dood.

      • Dan Trepanier

        I completely agree, aside from the $ part. You can be well dressed on any budget, no matter where you live, with things like eBay, etsy, online vintage etc… I’m living proof, I won “America’s Best Dressed Real Man” on a broke college student’s budget. We’ll be doing more advice-driven content on the topic soon…

        As far as the belt, you’re the second or third guy to show love for it – it’s a mustang seatbelt! haha.

        Thanks for reading!

    • Gazman

      The three button suit jacket with high button stance was all the rage in the early to mid 2000s. Most of the highly regarded designer brands put them out. Just another example of why one should ignore ‘fashion-forward’ clothes, especially ones that look naff at the time. You can be sure they’ll look even sillier in the future. A case in point now is the heavily cropped suit jacket. We’ll all be cringing about this look in the very near future.

      • TO

        Hopefully this applies to the word “swag” too.

    • Ron

      I’ll be a voice of dissent. Look 1, the jacket: Fitted is one thing; this is ill-fitted. Look 2, bland and so not him. Look 3, there’s nothing wrong with it per se, but now he looks like tens of thousands of other young New York execs. My main problem: Though I didn’t like the three “before” outfits, in the “after” looks, Mike has disappeared–in his place is this generic mannequin. I hope after this makeover that he loosened up, mussed his hair and regained some of the charm and individuality of his earlier look.

      • True_Tech

        I agree a bit with your latter point, his individual choices, aren’t there yet, but being a recent make over he’ll start to get himself more into the looks. add the chucks back, learn to have fun with the bowling shirt etc. When you start out you emulate, as you get more comfortable you innovate. As they say, now that he knows the rules, he can learn when/how to break them.

        • Dan Trepanier

          This was my main concern with this post…being that we had limited time and resources (one hour, two stores).

          It was a little difficult to get his personality to shine through properly, since Mike has such a unique and endearing personality.

          As a stylist, it’s very important to keep this in mind for your clients. We’ll touch more on this topic again soon, in our new section of TSB related to careers in style/fashion…


      • Dan Trepanier

        I see where you’re coming from…but what’s ill fitting about the jacket in look 1? For off-the-rack that’s pretty damn good…

    • Obtuse Observer

      Why does everyone always love to have a dropped shoulder? It’s getting a little comical now…

      • Dan Trepanier


    • Gazman

      Speaking of wide 80s cut shoulders with heavy pads, is it possible to have pads removed? If so, does this mess with the jacket too much…is it worth it?

      • David Hoang

        You never want to alter the shoulders of a blazer/jacket. It’s one of the hardest things to do properly in terms of tailoring.

        • Dan Trepanier


      • Dan Trepanier

        Not worth it in 99% of cases.

    • Akil M.

      This was a great post all three looks are on point and it sends the right message about being a young professional.

      • Dan Trepanier

        Thanks Akil! What’s up with your feature?? Let’s make it happen!

    • Theguybehindthelens

      A perfect example of what a change it clothes and a bit of grooming can do for a guy. This is an unbelievable transformation. I don’t mind of the suit supply pieces since the looks are so damn sharp.

    • Badger

      Look #1 is great, and the haircut is right on the money.

    • http://undefined Mr E

      The ‘after ‘ looks are without question an improvement on the chap, but they also make him seem like a Dan Trepanier clone.

      I could Photoshop your head onto each one of those looks and no-one would be the wiser.

      • Dan Trepanier

        Hmmm…I guess that’s a good thing for my brand. In time Mike will learn to put his own aesthetic into his new look. Funny you say that, though, considering how many compromises I had to make with the styling here, given the time frame and limited product sponsors.

        Nevertheless, thank for reading!

        • Alex

          Mr. E, we’re all clones. We all learned from someone. Your first two sentences here, Dan, yes. Good on ya. We learn some basics, then adopt what resonates long term. There’s no ‘first’, anymore, fellas. Just you.

      • jack

        I have to agree, but considering I ‘agree’ with his aesthetic, I don’t mind it one bit.

    • cam

      no more $15 haircuts and a few tailored pieces = all the difference in the world (first-hand experience)

    • TJ

      This is a great post! Mike looks like a totally different man.

    • Brent Kuz

      Question for mike or Dan if mike isn’t available. Work is one thing but how do your friends view it? Any resentment or questioning? Most people are gradual with a style upgrade really was wondering how the overnight change worked for you. Also did you add other pieces to your wardrobe so it’s not dapper one day and back to square one the next.

      • Mike

        Hey Brent, Mike here.

        I think the questioning/surprise factor for a lot of my friends and colleagues was diminished slightly by the fact that I told them I was doing this, so they knew a change was coming. Still, though, aside from some good-natured ribbing from my closest friends, the reaction has been overwhelmingly positive. The haircut, especially, gets a lot of comments.

        As for not having to go back to square one, the guys helped me pick some things from my closet that could look good with a little bit of tailoring, and gave me some tips as to what and how to purchase in the future. There’s no way I could revert to the “before” looks after realizing how awesome it is to look as good as I do in the “after” photos! Thanks everyone for your nice comments.

        • Brent Kuz

          Roger that! Would be cool to see the pieces you already have that you tailored or later on how you advance the wardrobe with your personal style.

    • John B

      He looks like a completely different person on the after looks! To be honest, the sponsors don’t bother me at all, unless you wouldn’t personally wear these clothes.

      • Dan Trepanier

        As a rule, we NEVER feature product that we wouldn’t genuinely recommend.

        We turn down ALOT of $ in sponsorship requests to keep our content authentic…keeping it real is key.

    • Jeremy

      Great job as always with the upgrade. Mike looks amazing. Very helpful tips on things to look out for when thrifting jackets/suits. Keep up the good work.


    • http://undefined Jeanscuffed

      An ad for Suit Supply or not, the focus is not on the brand as you could go cheapy, add a tailor and achieve the same look/fit but the focus is on the transition Mike has made. Wonderfully done guys. It doesn’t matter if the blazer, trousers, shirt n tie were picked up from different brands/places. If confidence and physical aesthetic is what was achieved then the goal has been met. Look 1: SICK!!

      • Dan Trepanier

        Well said! Thanks brother

      • Dan Trepanier

        Well said brother. Thank you.

    • Adam

      Man, you guys did a great job here. I’m really digging the light navy suit in the last look…I’m planning on snagging a suit this fall, leaning towards SuitSupply, and that suit just jumped to the top of my list. My only criticism is the shirt sleeves look long (or jacket sleeves short) in both 1 and 3. Besides that, loving what you guys did here. I feel like I should take a few steps back in my style education so that I can be a candidate for a TSB upgrade, haha!

      • Brent Kuz

        I agree I was thinking the same thing, appears to be a lot of cuff.

      • http://undefined Mxolisi Ngonelo

        Clearly you guys didn’t bother to read; just looked at the pictures.

        • Adam

          I’m not sure what you meant by this…I see the explanation in the comments here (perfectly good explanation too), but did I miss something in the articles? I do read them…pretty thoroughly…

    • Olav Kvarme

      Great post, as usual! I’ve been curious about Suit Supply for some time, and these pictures are really convincing. Would you mind sharing with us what fits/models Mike is wearing from the Suit Supply Lines? (both jacket in look 1 and suit in look 3). Thanks!

      • Wieczorek

        As far as I can see, the suit is Washington (notice the peak lapels and ticket pocket) and the jacket is Washington Half, their casual take on Wahsington (still, peak lapels, but less constructed, shorter jacket length and patch pocket). Though my honest opinion is that peak lapels look best in tuxedos and double breasted jackets. Single breasted ones look for me most appealing with wide notch lapels.

    • Anonymous

      That’s the same guy?? He looks so much more suave, confident and handsome. As a female reader the “after” guy is hot!!

    • carlos

      Its like to different people…
      Looking good Mike, keep it up

      • Brady P

        I thought the same thing! Amazing what the right clothes can do

        • Dan Trepanier

          True. Not only do they make you look better, they make you feel better…and people certainly notice the later as well

    • LouCaves

      I kept saying WOW after scrolling down to the each of the “after” pictures.

      Two words: Very well done. :)

    • Troy

      Is it just me or do the sleeve lengths in looks 1 and 3 seem a bit off? Other than that great post. I really enjoy the upgrade posts, and hope you keep more of these coming!

      • Dan Trepanier

        Shirt sleeves are a touch long since the cuffs are too wide for Mike’s wrists. Looking back we should have taken the time to move the cuff buttons inward so they wouldn’t creep down on the hands… An easy fix nonetheless.


        • M.

          Always true to what you guys do.
          No wonder you made it this far.
          This post is great, and Mike is a lucky guy. :D

    • BJ

      This would be better if it wasn’t a Suit Supply ad.

      • Dan Trepanier

        Agreed. We were on a tight timeline before we left for the west coast, and we needed a brand sponsor who was willing to let us film our TV pilot in the store on short notice… My friend Nish from Suit Supply hooked it up.

        The whole thing was a little rushed, truthfully. Next one(s) will be more diverse.

        Thanks for reading!

      • http://undefined Robert

        Ha, I was thinking the same thing.

      • BF

        99% of guys would look better if they bought 99% of their clothes from Suitsupply.

    • BF