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

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“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.”

  • Navy silk polka dot pocket square by Ted Baker

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

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“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…”

  • Shades by Ray-Ban ·
  • Canvas/leather tote bag by Ted Baker

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.”

  • Tortoise shades by Matsuda Eyewear ·
  • “UBugMe” pocket square by Ted Baker ·
  • “Nubran” Grain Brown Leather briefcase by Ted Baker

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.