The Gentleman’s Four Step Guide To Personal Style

Having grown up just outside of the city of Boston, I have been able to humbly brag about the praises showered upon us by magazines such as GQ. Boston is frequently #1 on their lists, and who could ever be upset about that?

Well…that depends on what the list is for.

Boston is, repeatedly, GQ’s #1 worst dressed city in all of America. Yay!

While there is a thriving fashion scene in Boston, we often need to know where to look in order to find it. It is often overshadowed by college students schlepping to class in their hoodies and cargo shorts (unless it’s cold out, then we get the sweat pants). But for one stylish week each year there is a chance for fashionable Bostonians to stand up and be appreciated. For both designers and consumers, Boston Fashion Week is the super bowl of self-expression.

I am also excited to announce I will be the official Red Carpet Emerging Style Correspondent at the 7th annual Emerging Trends Runway Show, styled by Gate 26. If you are in Boston, get your tickets here!


Our personal style is how we tell the world who we are. It is reflective of our personality and it is quite literally our face to the public. How we choose to dress is synonymous with how we want others to perceive us. There is no ‘right’ or ‘wrong’ when it comes to style. There is just – you.

So in order to develop a personal style, which is often ever-evolving, there are a few things to always keep in mind, which we will discuss below. In this article I will focus on men, but for women, if you are looking for great looks that double as both classy and sexy, look no further than Allie is a Boston based fashion blogger who, in my opinion, gets it right.

Men, pay attention to fit.

The way your clothes fit and making sure to dress for your body type is absolutely essential. I love wearing suits and I also love the slim fit look, but I am not a slim person, so I need to compensate accordingly. I need to make sure I wear the size I need and not the size I wish I needed. I need to make sure that my jacket is fitted and not tight. There is a big difference.

Using the example of suits for men, regardless of what brand you’re wearing or how much your garments cost, they will look terrible if they are too big or too small. If your sleeves or pants are too long or short. What really matters the most is the fit. While more expensive brands often have a better cut and material, obviously every body type is different and needs to be treated accordingly. This often means having a jacket tailored or even made for you rather than just pulling it off the rack and hoping it fits.


For an in-depth look at how your suit should fit, click here.

But obviously, suits are not the only thing that we wear. Maybe you don’t wear suits at all, and prefer denim and t-shirts. If you are wearing jeans, the first thing to do is throw out your lighter baggy denim and replace it with a darker, slimmer fit. Darker wash denim is more stylish and versatile, able to be worn with essentially any choice of shoes, shirt, or jacket. Premium denim is always worth the extra money because it is an investment that will last you far longer than a cheaper brand, they will be more durable, and also fit better.

Since all premium denim is cut differently, it is best to conduct your own trial-and-error with different brands and styles in order to determine what best suits your body type. Generally speaking, a straight leg is typically best as it will fall nicely along the top of your shoe. Super skinny jeans are a good option as well if you plan on sharing them with your girlfriend. (Just kidding, guys).

For more information on finding the right denim for you, click here.

Dressing for the occasion.

Personal style is dynamic. It needs to be translated consistently depending on where we are going and what we are doing. The good news is, whether we are staying more relaxed or having a more formal night on the evening, the level of style we project does not need to waver.

One big issue I often face is dressing properly for a date. It should go without saying that gym sneakers or hoodies or cargo pants (just stop that) should be left tucked into a dark corner when meeting a potential mate for the first time. But, unfortunately, it doesn’t. Someone has to say it, and I’m saying it now.

Below is a quick visual graphic courtesy of which effectively outlines how to approach dressing for a variety of occasions. Once you have developed your personal identity you will have the ability to translate it into a color and pattern scheme that suits you and is equally appropriate for any given occasion.


Take risks.

I’m about to divulge a personal secret about myself. I was not always the suit-wearing gent that I fancy myself to be today. Yes, I had a mohawk. Yes, I had a collection of ripped jeans. Yes, I wore too much jewelry. Yes, I wore bright pink graphic t-shirts. But, at the time, it was how I wanted to portray myself and I was obviously living a much different life.

But, it worked.

It worked because it was bold and it was different and it wasn’t what you would see every day. It fit with the people I was spending time with and the places that I was going. Needless to say, that clothing has been left in closed drawers for years and is now only suitable for Halloween costumes. But the important thing is that it served as a necessary stepping stone in the evolution of my style, the edge of which I have refined and carried into how I dress today.

When we think of our style as a personal expression of ourselves, it suddenly becomes less appealing to dress like everyone else, and we become more motivated to get creative and ask ourselves how we really want to be seen. Often times this entails trying new things and experimenting with different items we may not have pictured ourselves wearing. Keep an eye on your favorite actors in movies and TV shows. Do any of them look like you? Do they have a similar body type? Watch how they dress and take cues on new ways to expand your horizons. It is a constant learning process.


Realize that expensive does not equal stylish.

If you need any further proof of this statement, think back just a few short years ago when everyone was spending $200 on Ed Hardy t-shirts that were bedazzled with hundreds of rhinestones and should have come with a pair of sunglasses just to be able to look at them. Expensive, trendy, but not stylish.

And while some accessories such as belts or wallets or shoes are a nice accent with a branded pattern, the brand does not make the man and should be understated. We have evolved.

If you want, you can go spend $800 on sneakers that look like moon boots, but it doesn’t mean you’re going to look good doing it. You can take a quarter of that money, go to a smaller boutique store and piece together an entire outfit and have multiple pieces you can interchange for different occasions.

Paying 400 dollars for a t-shirt with some abstract design on it that might sort of be a robot or a tree in there somewhere I don’t know, doesn’t make you stylish.

“Fashion is what you buy, style is what you do with it.” Style is about the personal twist you put on it. The unique way you carry yourself, and developing the looks that make you feel the best. When you look better, you feel better. And when you feel better, you do better.


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5 thoughts on “The Gentleman’s Four Step Guide To Personal Style

  1. Good post as always, but I feel I must add that there are plenty of intelligent, decent women like myself who find light-colored jeans very attractive (provided they fit properly & don’t look like they’ve been through a woodchipper, of course). Maybe it is just a Southern thing though…

  2. 1) fit
    2) Fit

    If nothing you get from this, fit is king. Gentleman, even if you are a bit heavier, make sure your clothing fits. Buying mugger just makes you look bigger. Buying small makes you look uncomfortable, stiff, and will eventually destroy your clothing. Good luck all!

  3. Hi James,

    I was doing some research on jeans when i chance upon this page

    I noticed that you link to one of my favorite articles on jeans, the denim guide for men from Esquire.

    Anyway, just to give you a heads up, i created something similar but more detailed and up to date with regards to wearing the right shoes with your different styles, colors and shades of jeans for men.

    Might be worth a mention on your page.

    Stay Awesome!


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