My Style Story:

Back when I was in college, my style left a lot to be desired. 

Up until that point, I really hadn’t thought much about the way I dressed, or the way a man’s overall look can make an impression, both on his own sense of self, and on the people he encounters.

This was the early 2000s, when bands like Dashboard Confessional and Fallout Boy were at the peak of their fame, and I tended to dress like the kind of overly emotional sad sack sensitive introvert who loved that style of shrill emo nonsense emotive pop-punk. 

An Eye-Opening Encounter 

While I didn’t have much style to speak of, I did have a few good friends, and one summer we all decided to go visit our respective childhood homes and meet each other’s parents and siblings. 

One day we were sitting in the backyard of my friend’s mom and step-dad, Glen. 

Glen mentioned that he was a member of the same golf club where my grandfather golfed, so I asked if he might know him.   

His answer was immediate. And, in retrospect, kind of life-changing.  

“Oh, your Angelo’s grandson? He’s such a gentleman!” 

I had never met Glen before, and while he was perfectly polite before finding out who my grandpa was, afterwards he was warm, welcoming, and all too happy to regale me with stories. 

He told me all about how my grandpa was a classic gentleman in every sense of the word: 

Always smiling, always willing to help out a friend, always well mannered, and – of course – always well dressed.  

“They don’t make them like that anymore.”

The Best-Dressed (and Best-Mannered) Guy in the Room

On the one hand, it shouldn’t have shocked me to hear this. 

My grandpa had always been both the best-dressed guy in the room and the best-mannered. 

But it had never occurred to me just how closely connected those two concepts really are. 

It wasn’t until I heard Glen saying such positive things about my grandpa that I realized that that’s exactly how I want other people to talk about me. 

And since Glen was clearly impressed by the fact that my grandpa was both well-mannered and well-dressed, in that moment I realized that the best way for me to start acting like a modern gentleman would be to start dressing like one. 

Look Good, Live Well
(& Laugh Often) 

It’s been (checks calendar in bewilderment) almost 20 years since that chance encounter with Glen (sigh), and I’ve spent the better part of those two decades more or less obsessed with style. 

For decades I’ve read damn near every issue of style magazines like GQ and Esquire that I could get my hands on. 

I’ve obsessed over TV shows and movies that featured well-dressed leading men, including everything from Mad Men, Suits and White Collar to movies like Crazy Stupid Love, Ocean’s 11 (both of them), The Thomas Crown Affair (the good one, not the shitty Pierce Brosnan one), and the James Bond films (again, the good ones, not the shitty Pierce Brosnan ones).  

And I’ve spent way more time at the mall than could possibly be healthy, examining the latest styles, trying on clothes to see how they fit, feel and move, and talking the ears off of those poor, unsuspecting department store clerks, who realized far too late that I was mostly there for educational purposes, not to actually buy anything. (Sorry guys.) 

And just to be clear, I can’t claim to be as well-dressed as my stylish-ass grandfather – who still inspires me to this day – or even half as gregarious or gentlemanly. 

(He would never mislead department store clerks like that.) 

But what I can say is that I’m a helluva lot closer to his lofty standards than I would have been if I had never bothered to study the finer points of style, grooming and self-improvement. 

Learning how to look good has enabled me to live well, and I consider it a true honor to be able to share what I’ve learned with other guys so they can do the same. 

Thank you for taking the time to read my style story, and for not telling Pierce Brosnan how many shots I took at him. 

(I kid because I love Pierce, you square-jawed slab of man, you.) 

Start Your Style Story ↓↓

If you’re ready to get your own style story started, check out our post about how to dress better for guys to discover a few fundamental lessons you can apply to your look and your life. 

And if you’re looking for more advice, don’t worry:

We’ve got lots. (It’s kind of our whole deal.)

Check out our men’s style advice category to find literally hundreds of insightful, in-depth (and occasionally entertaining) articles on how to look sharp and stand out, or peruse a few of our favorite featured articles below.