Take any outfit, and there will always be a group who is very much in favor of said outfit, thinking it’s the greatest outfit known to man.

On the flip side, there will be another group out there who thinks that same outfit is THE worst and wouldn’t be caught dead in it.

I was having this exact conversation with a friend the other day and we were laughing at how subjective the topic of personal style is. There is no right or wrong answer; it truly is based on one’s opinion.

There is no better evidence of this than when you’re scrolling through the king of curation websites, Tumblr.

There are many times I see a picture of an outfit posted and hundreds of likes, reposts and comments below it… But I take one look at the thing and to me, it’s the most hideous pairing ever.

Who’s wrong and who’s right?

More importantly, who’s to say something is absolutely good style or absolutely terrible style? Everyone has slightly different taste, and in all honesty, no one is fully right or wrong.

So where does that leave you, the student of style? How are you supposed to decipher if you’re stylish, if you’re trendy, or if you just missed the mark all together?

Well, here’s how.

1. Understand the basics

You read EG, so that’s a positive step forward. Here at EG we love the basics, reason being is that the basics—the foundation of rules with which you build your personal style—never really change.

Once you have these down, you can deviate as much or as little as you desire… it’s really up to you.

2. Know what constitutes a good fit

Everyone’s definition of a good fit is different, because everyone’s body composition is different. This is the most important thing to understand.

You can be the most stylish dude in your office, but if you’re a hanger for your clothes, you don’t look as good as you think. And if you’re bursting at the seams, that’s not a good look, either.

The first step to getting a grasp on good fit? Measure yourself.

3. Wear what you like

Once you’ve nailed down the standard style rules that dictate basic, classic style (and hopefully you’ve learned a majority of them through EG), take a step back and evaluate what you like.

Yes, even the “rules” that have been set. What do you agree with and what would you like to deviate from? Explore that.

For example, we all know a nice pair of dark denim is the perfect addition to any man’s lean wardrobe because you can wear it in many situations, both dressed up and dressed down.

But what if you really like the look of washed and faded denim? Who says that can’t be stylish? Certainly not these guys pictured here.

Your personal style is what you decide it to be, not what some personal stylist, fashion icon, menswear blogger, or celebrity tells you is stylish.

And that’s also where understanding the distinction between fashion and style comes into play. We often use the two interchangeably, but there’s actually a difference.

Think of it this way:

Fashion is the clothing that comes out season after season.
Style is how you decide to wear it.

(Don’t attribute that quote to me; I’m sure I picked it up from somewhere else. But regardless, truer words haven’t been spoken.)

4. Wear what feels most comfortable

There’s no sense in wearing something deemed stylish or good-looking if you’re simply not comfortable in it.

That’s not to say you should wear baggy jeans because you don’t like how the denim hugs your thighs in straight leg jeans. Man up, wussy. Remember, fit is paramount.

But if your lifestyle dictates that casual is the best wardrobe style based on what you do day to day, don’t feel like you have to wear a suit to look good. (But if it’s a special occasion, throw a blazer and some dark denim on once in a while, please.)

Point is, there’s a way to be stylish, comfortable, and put-together, no matter what type of lifestyle you have… whether you’re a construction worker or an investment banker. You just have to know how to do it.

We on the same page here?

It’s not about fashion, it’s not about what someone else says is cool to wear or following what’s “on-trend”.

Understand the basics of men’s clothing, what to wear when, and how things should fit. Then determine what type of clothing you like, and cautiously (yet confidently) break the rules. Yep! Break em.

Hopefully this is helpful to you guys out there who aren’t quite sure what step to take, or what to follow when it comes to determining your own style. If you want a more all-encompassing system to follow, you can always check out Graduating Your Style.

Comments / questions? Let’s hear em!



[photo, light denim photos

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10 Responses

  1. Robert van Tongeren on

    Wow, Barron. You seem to have taken all the most important style lessons I’ve learned over the years and put them into one awesome article. Love it.

    I really connected with the part about feeling comfortable in your clothes. I would add though, that it’s also good to step outside of your comfort zone from time to time. That’s how we evolve after all.

    When you feel uncomfortable wearing something because it doesn’t fit with your lifestyle and/or identity, then don’t wear it.

    However, if you don’t feel comfortable wearing something because you’re worried about people’s reactions, I’d encourage you to do it anyway.

    When I was reinventing my style, there was a lot of advice telling me that a suit is essential. I almost felt obligated to get one, even though I didn’t feel connected to the look at all.

    I think suits can look great, they just aren’t for me. I’m glad I realized that and didn’t get persuaded.

    On the other hand, I wanted a blazer quite badly, but whenever I tried one on, I would just hang it back on the rack, worrying about what my friends would think.

    When I finally did get a blazer, I felt weird wearing it for the first couple of times. It made me look awesome, and I knew it. I just wasn’t comfortable wearing it yet.

    The discomfort wore off though, and now I absolutely LOVE wearing it.

    I have heard from guys who had similar experiences when they moved from the 24/7 T-shirt look to wearing dress shirts. I guess many guys feel the same way when they step outside of their comfort zone.

    But it’s a step that’s important to take.

    • Barron on

      Thanks for sharing that Robert! Great points; it really just takes getting used to a new (better, or different) style than what you’re currently wearing.

      When I wrote the part about being comfortable, I meant literally and physically comfortable, not just mentally comfortable wearing something you’re not used to 🙂 But great follow-up points nonetheless.

  2. Joe Han Lee on

    I like this article a lot. It really tells us to be ourselves
    when it comes to wear something that makes us feel good and comfortable. As a
    jewellery designer and artist, I fell that men should also show some courage to
    wear some pieces of jewellery that are more unique than any other men’s
    jewellery. Therefore there are no set of rules and right or wrong answers on
    how a man should wear their jewellery. It is all about their preferences.

    Here is my jewellery etsy store and my facebook page if you
    would like to check it out:



    Thank you,

    Joe Han Lee

  3. Emil Bakeev on

    And how many rules should we break? “It depends” I guess is the answer. So far I am wearing my sports watch with a suit and on my right hand, use pocket squares that don’t really match my shirt or tie and wear only black socks. What else can I safely break if I should wear only grey and navy business suits, formal shoes and no jewellery?