Men: Here’s How To Dress Well, No Matter Where You’re Headed

by Barron Cuadro  |  in Style Tips

So if you’re reading this article, I’m going to assume you want to learn how to dress well. You don’t want to dress too young or trendy, but not too formal, either. You want to dress sharp (but still casual), and you want it to be effortless.

I hear ya. Most of us guys just want to dress well, not dress up. You want to look well put together, but still feel comfortable.

You want an outfit that’s a step or two above the standard jeans-and-tee look… something you can wear to run a few errands, grab a drink with friends, or have an impromptu dinner with your partner, without ever feeling sloppy or under-dressed.

Luckily for you, it isn’t difficult to dress well. You don’t need a big budget, tons of clothes, or hours upon hours figuring out what to wear.

Style Principles, Not Rules

In this article, I’m gonna hook you up with the essential style principles. These principles will help guide you on your path to dressing well. They will continue to serve you as you form and evolve your own personal style.

Here’s the thing.

Other articles may give you exact, definitive style “rules” like:

  • “Never wear black and brown together.”
  • “Always match your metal jewelry and accessories.”
  • “Invest in a good suit.”

While some of these style rules make sense, I’ve always felt that focusing on rules is too tactical, not foundational.

…like missing the forest for the trees.

What good are specific tactics and rules without having a solid understanding of and foundation for your personal style?

Plus, there are simply too many style rules to remember, and without that foundation, how do you know which ones apply to you, and which ones to ignore? (Show me a “must-follow” style rule, and I’ll show you an Instagram photo of a stylish guy breaking that rule and doing it well.)

By the way:

illustration of men's clothing
YOU’ll Love This One Too!

How To Build A Minimalist Wardrobe For Men

These Easy-To-Follow Style Principles Will Make Dressing Well Much Easier

Instead of giving you set-in-stone style rules, I want to provide a set of style principles instead.

These are overarching ideas that will guide you as you develop your personal style. Internalize them. It will make your journey towards better personal style much, much smoother.

1. Copy, Imitate, Steal Your Style

Independent filmmaker Jim Jarmusch has a famous quote. He’s referring to the art of filmmaking and creativity in general, but I believe it applies to personal style as well. Here’s how it starts:

Nothing is original. Steal from anywhere that resonates with inspiration or fuels your imagination.

Read all of Jim Jarmusch’s Golden Rules

It’s a much longer quote (read it here), but essentially, you want to imitate styles that you like, especially if you’re just starting out. It’s the only way to get started on improving your style!

Everyone, even the most stylish guys in the world, find inspiration in other places. They don’t just invent great style out of thin air. They were inspired by someone or something.

So if you’re just starting out on your style journey, don’t be afraid to imitate, copy, and steal looks you think are cool. I do this all the time. It’s the only way to evolve and elevate your style. You’re drawn to a certain look or style, you find guys who are doing it well, and you give it a shot.

Start paying attention to how guys dress. They could be real people in your life, actors and celebrities, even characters in movies you’ve seen.

Don’t worry if it’s “right” or “wrong”. Don’t even worry about why you like something. Simply take note of clothing or styles you’re drawn to. Outfits that you think look great.

Soon enough, you’ll form an opinion about style, what you like and don’t like. You’ll develop an eye for what looks good. From there, try some of those looks. Start with just one piece of clothing, and experiment further when you’re ready.

Once it feels natural, once you’re in your groove, you will find ways to make that look your own.

Eventually, you will have invented your own look that’s unique to you, a combination of the different styles you’ve been inspired by over months and years of experimentation.

2. Money Can Buy Great Clothes, But Not Great Style

If you think you need tons of money to dress well, that’s simply not the case. And that’s a good thing, because a lack of money shouldn’t be a reason to not dress well.

Great style can be had on a $10,000 budget or a $100 budget. It’s just a matter of knowing where to look, and what to look for.

To put it another way, money can buy great clothes, but it can’t buy great style. So don’t be discouraged if you’re a college student on a shoestring budget, a young man still building his career, or even an older guy on a limited budget. There are options out there for you.

Upgrade your closet one item at a time and take your time doing so. Find affordable alternatives, and only splurge on items that you can wear for years and years (like a great pair of dress shoes).

3. Fit > Quality > Brand

Always follow this formula. This is the order of importance when it comes to dressing well.

Fit always trumps everything, so focus on fit first. A $2,000 suit isn’t impressive if it’s ill-fitting. A $200 suit that’s been impeccably tailored, however, is ultra impressive. Again, it’s not always about how much you spend; it’s about the way the garments fit you.

When you have a bit more cash to spend, you can start to consider the quality of a garment. Quality often costs money because of the time and effort it takes to create something of great quality. These items also tend to last longer, or are constructed better, or are made from finer materials… so spending that extra amount can be worth it.

Generally speaking, a great brand with a storied history typically has good quality built in. That’s not always the case, but for the most part, it’s true. A company doesn’t survive for 25, 50, 100 years by producing crappy products.

But, in my opinion, what it all comes down to is fit.

4. a lean wardrobe Is All You Need

If you want a versatile wardrobe that makes it easy to get dressed for any occasion, focus on the few key pieces you need to create a number of great outfits. I call this The List Of Essentials.

You can find a partial list in my article about how to dress in your 40s (and beyond). That list is a great place to start. Yes, even if you’re just in your 30s… or even if you’re in your 60s.

Having a tightly edited set of clothes in muted, neutral, and earth-tone colors is a complete game changer.

Wear everything you own

You don’t need 25 pairs of denim, you can get by with two or three. Do you really need 500 shirts in every color? You probably wear the same 5 shirts every week. Keep a few, discard the rest.

Fewer is better than too much. Too many things leads to indecisiveness, which leads to you wearing the same jeans and tee every day. Wear everything you own.

How To Identify The Clothes You Don’t Wear And Get rid of the clutter

If you don’t wear it, get rid of it. In Smart Sharp Style, I describe my foolproof method of wardrobe cleansing.

Essentially you empty your closet completely, placing all your clothes in a separate closet or different room. If you’re low on space, designate part of your closet as your Lean Wardrobe Zone. It should be completely cleared out and ready for the next part of this process.

As you put together outfits every morning from your clothes in the other closet, you’ll wear them, and then hang them back up in your main closet (a.k.a. your Lean Wardrobe Zone). You’ll repeat this step every day.

After a couple months (maybe even just a few weeks) it will become clear which clothes you wear the most, and which ones you’re just keeping around for no apparent reason. At that point, you’ll know what to get rid of.


5. When it comes to Colors, Complement > match

The key to matching colors is to never match your colors.


You want the colors in your outfit to complement each other. It doesn’t take an advanced degree in design and color theory, but understanding color relationships does help, and so does having a good eye.

The good eye thing you can develop through daily practice.

Looking for a place to start? Menswear neutrals is my number one suggestion. Memorize these colors, and you’ll be able to wear any outfit and put together any other color combination.

6. Make one small change at a time

Think marathon, not sprint. You don’t have to rush into upgrading your style. Besides, you can’t change completely in one day, or even one month… especially if you’re starting from scratch.

Developing a taste for what you like, forming good style habits, and implementing change takes time. Don’t get frustrated if it doesn’t all make sense to you right away.

Start with one element and improve on that. Take as much time as you need. Move on when you’re ready.

You can start with one piece (e.g. upgrading your denim is a great place to start), or one aspect of your style (i.e. fit). Do your research, learn the right from the wrong, implement, and improve.

There’s all this noise, all these resources, and so many different people telling you what to do and how to do it.

I think the most important person you need to listen to is yourself. If a piece of information doesn’t sit well with you, no need to blindly accept it or the person giving it to you (even if that’s me).

7. Dressing well is about more than looking good

It’s about feeling good, beng confident and self-assured.

It’s about dressing with a purpose. How you dress says a lot about your confidence, what you think about yourself, and how you expect others to treat and regard you.

A well-dressed man garners more respect than a disheveled dude in an ill-fitting tee and baggy, faded jeans. You can disagree, but doesn’t make it any less true! We judge books by their covers.

If you want to dress well, and you want it to be a long-term lifestyle change, it may help to identify your motivations for doing so.

Maybe you want to…

  • be respected among your superiors and colleagues at work.
  • appear more professional.
  • look less like a college student and more like a man that’s got his stuff together.
  • be taken more seriously, to project more confidence, to put your best foot forward.
  • meet someone special, and to know that you look your best.

Whatever your reason may be, dress every morning with that in mind. And hopefully, by dressing better, you’ll start to feel better and project more confidence.

Most of these reasons and desires can’t be satisfied simply by dressing better. You have to be those things and know those things. But, dressing better and feeling great in your clothing certainly helps.

Confidence, my friend. Confidence is the name of the game.

8. Not all Style Rules Will Apply To You

I hinted at this a few times, but not every style rule or tip will apply to you.

Yes, even the tips you read on GQ, find on a fashion website, or watch on a fashion YouTube video. Some will, some won’t.

But that also doesn’t mean those rules are “wrong”… they’re just not right, for you.

You have to take every piece of advice you read (not just from EG, but from wherever you get your information) and decide whether or not it’s applicable to you. Take the pieces that make sense, implement them, and discard the rest. It’s simple.

Follow These Style Principles To Dress Well… For Life

I hope these overarching principles help clarify what good style means (or can mean).

It’s not about:

  • overdoing it on trends,
  • or dressing in suits seven days a week,
  • or spending all your hard-earned cash on the latest and greatest, trendy garments.

It’s about making simple improvements consistently as you form your own personal style.

It’s about taking any set of style rules you find, and having the confidence to use what applies to you while discarding the rest.

And realize your style will always evolve. It’s not something that stays the same forever. So internalizing these principles will serve you well now, and in the future.

You can do this!

If you have any questions or comments, hit me up on Twitter. You can also find join other readers on Effortless Gent’s Facebook page, or DM me on Instagram!