Case Study: 2 Bloggers Who Stepped Up Their Style

Here on The Modest Man, I like to write about famous men of modest height, like rockstars and actors. I do this for two reasons:

  1. To showcase and dissect their style in order to find out what they're doing right and what mistakes they're making (and what we can learn from them)
  2. To inspire shorter gents who might feel handicapped or held back by their build (if Peter Dinklage didn't let it hold him back, no one should).

But there are examples of stylish short gents all around us. They aren't big shot celebrities or famous athletes. Just normal guys who care about their appearance. You see them on the train, in the store, at work and, of course, on the internet.

As a writer, I try to keep up with all of the best blogs. Two of my favorites are run by shorter guys who have noticeably stepped up their style over the years. Let's take a look at their evolution and see what we can learn from them.

Derek Halpern

Derek runs a blog called Social Triggers. It's all about psychology and marketing, and it's extremely interesting. I don't know exactly how tall Derek is, but I'm going to guess he's around 5'6″. He's built, though, with broad shoulders and a wide chest.

When he first started making videos and giving presentations, he wasn't exactly the most stylish man in the room:

Derek Before

Not terrible, but not great. His suits aren't tailored to flatter his body type, his haircut is sloppy, and his color choices are all over the place. Notice the broad horizontal stripes, which don't flatter the shorter body type.

Derek could often be found in Lacoste tees and Henley shirts, which are a bit too casual to wear in front of an audience or camera. You could find him in a suit jacket from time to time, but there were issues with how they fit.

Fast forward to present day, and he looks like this:

Derek After

Pretty sharp, eh? Sure, the $310 haircut helps, but it's not just that. He is making an effort and dressing up. You don't see him in t-shirts anymore. And his clothes actually fit. I'd be willing to bet that they're custom, or at least altered by his neighborhood tailor.

He's paying attention to the details. Notice the roped shoulders on his suit jacket, an Italian style detail that flatters his build nicely.

He's wearing colors that work very well with his skin tone. The contrast and saturation levels are spot on. (If you want to know more about choosing colors based on contrast, my friend Robert wrote a great article about that very subject right over here.)

Now, Derek is a confident man by default. The kind of guy who commands attention when he walks into the room. He's from New York, and I don't think anyone ever told him he was short, because he presents himself like he's seven feet tall.

That said, he has personally observed that wearing a suit influences the way people treat him when he's out and about. Derek is an expert in psychology, and he realizes that dressing sharp has a positive effect on the way he's perceived.

And I agree.

Let's move on to our second blogger, Mr. Pat Flynn.

Pat Flynn

In the blogging world, Pat Flynn is what you would call a “rockstar”. He's got a site called Smart Passive Income that teaches people how to make money online and retire early. Sounds nice, doesn't it?

It is.

So nice that's he's been invited to speak at conferences all over the world, which means he's no stranger to being in the spotlight. But he used to look, well, pretty darn average:

Pat Flynn Before

Note to Pat: Sorry, man, but I need to hate on you for a sec. Please know that I have nothing but love for you and your work.

Notice the sloppy, bright orange tie, the relaxed fit, light wash jeans dragging on the ground, the untucked shirts and the sneakers. Pat was clearly making an effort, but he didn't understand fit and color. Like so many men, he thought throwing a tie on automatically dresses up any outfit. He was trying to achieve an effortless look, but it backfired and looked too effortless.

Maybe it was the celebrity status that gave him the push he needed to start dressing better, but he started doing his homework and putting in the effort. Check out these recent photos:

Pat Flynn After

These days, Pat Flynn is rocking three piece suits, muted colors that compliment his (and his son's) skin tone, fitted jackets, tucked in shirts and dark wash jeans. He has a nice haircut, and you can see the confidence in his face.

Just look at that smile! That's the smile of a man who knows he looks good. Pat is probably about 5'7″ tall, and he is killing it in the business world. He's a great public speaker, and I have no doubt that his appearance contributes to his well-being and success.


Derek and Pat are doing amazing things with their blogs and businesses, but they're normal guys like you and me. They were dressing like most men – in clothes that fit okay and looked decent, at best. But they both chose to make a conscious effort to step up their style, and now they look a million times better.

Whether you do it for increased confidence, to attract a mate, to get a promotion or just to be taken seriously at work, take action to improve your appearance today. I promise, you won't regret it.

Hint: An easy way to get started is to use The Modest Man Style Guide!

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  1. I generally enjoy your Inspiration posts but this one in particular I really like. Probably because these are the types of celebrities I really look up to, more so than actors and recording artists!

    • Hey Evan,

      Thanks. Yeah, it’s nice to switch it up every now and then. After all, most of us don’t have celebrity budgets or personal stylists. If Pat Flynn and Derek Halpern can transform their style, anyone can. (Not that they’re doing too shabby themselves!).


  2. I thing Derek is doing a good job and it’s great how he upgraded his style.
    I hope he won’t stop here but get himself a pair of quality shoes. And by that I don’t mean Prada, Hugo Boss or anything similar.

  3. Love these gents and love this post! Awesome way to use the examples of “real guys”, not celebs, but folks who have a lot of photographs taken of them to illustrate that anyone in any industry is making these same impressions daily. Love your blog and think you’re providing such an awesome resource, mister!

    with grace & gumption, Hilary

    • Thanks for the comment, Hilary! You’re right that it’s more helpful to see real men who don’t have stylists, designer-everything, professional photographers and unlimited budgets. I’ll try to do more of these spotlights in the future.

      Btw, checked out your site. When is the “For the Gents” section re-launching?


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