Men: Want To Learn How To Be Stylish? Master These 10 Habits

by Team EG  |  in Style Tips

Have you ever noticed the way some guys are able to look better in jeans and a T-shirt than others do in a suit?

Everything about their look seems comfortable, confident, and nonchalant… yet deliberate at the same time. Even when wearing a suit, they just look like they were born in it… like it’s a second skin.

What is it about these individuals that sets them apart?

man in blue long sleeve shirt and white jeans and green loafers leaning back in chair

Anyone remotely interested in style strives for this effortlessly cool way of dressing. While it may come naturally to a rare few, for the rest of us, it takes some work to pull it all together.

Wouldn’t it be wonderful if we could just copy what we see and be guaranteed a perfectly polished style? In reality, there’s no set-in-stone formula for being stylish, such as “Well dressed women carry this brand of purse” or “Stylish men always wear suits.

It’s more complex than that.

Fortunately, there are some common habits amongst the naturally style-inclined that you can emulate.

“How Can I Look More Stylish?”

The following is a list of 10 Dos and Donts to keep in mind if you want to be stylish, along with my tips on implementing these habits in your daily life so you can become the confident, stylish man you’ve always wanted to be.

1. don’t have a closet full of “comfy” clothes

How do you dress impeccably day in and day out? Simple: don’t give yourself an option to do otherwise. If your wardrobe is full of baggy hoodies, graphic tees, and running shoes, you can bet that’s what you’ll gravitate toward.

If you limit these items to only what you absolutely need—perhaps a set of older clothes for yard work or fixer-upper sessions—your choice will default to either looking great… or looking amazing. It’s a win-win situation!

And “looking great” doesn’t mean “dressing formally”. You can look sharp in casual clothing. You can wear jeans and a T-shirt without looking sloppy, even around the house.

Helper Tip #1

Donate your comfy clothes and invest in classic staple items.

2. buy Clothing that gets better with age

Besides saving cash and being less wasteful, buying pieces built to last will give you an incredible aura of style. Well-worn items send the message that you know exactly where to spend your dollars.

Brock from The Modest Man and I chat a bit about this in the video below:

For the most part, natural materials are the name of the game. Leather, denim, canvas, and wool all tend to hold up (especially when taken care of) and develop a beautiful patina with normal use. Stylish people avoid items made of synthetic materials and faux design details.

I’d say the exceptions to this rule would be activewear, as well as underwear.

Plenty of underwear and training-focused brands design their garments with a mix of synthetics. These were specifically designed to wick away moisture, prevent bacteria or scents from lingering, maintain its shape no matter what you’re doing, or a combo of all three.

But for your regular, everyday clothing, stick with natural materials. That’s going to be your best choice overall.


Take your time when deciding on purchases. Read reviews and look for designs that haven’t changed much over the decades.

3. dress for the weather

It takes one minute, but can make a huge difference: Check the weather before you get dressed in the morning. Doing this will help determine what you should wear that day!

  • If it’s going to rain, you’ll know to don a rain coat and bring an umbrella
  • If it’s unexpectedly hotter / colder than it has been the past few days, you can adjust your outfit accordingly

Depending on where you live, your wardrobe may require certain items that aren’t necessary in every man’s wardrobe:

  • A winter down parka if you live in a cold climate
  • A trench, galoshes, and sturdy umbrella if you experience a lot of rain
  • A number of linen shirts if you live in a hot and humid environment

You get the idea. Knowing the weather before you get dressed will save you a ton of time and stress, will make sure you’re prepared for the day, and most importantly, will keep your clothes from getting ruined.


Prepare for changes in your local climate by having the appropriate types of clothing, accessories, and outerwear, no matter the season.

4. always “get dressed”, No Matter The Occasion

Stylish people make it a point to get dressed everyday, even on the weekends. They don’t lounge around until noon and then decide to stay in because they aren’t ready.

When you always look presentable, you’ll never miss an opportunity to grab an impromptu drink with friends, take a midday walk to get some fresh air, or meet up to chat with a prospective business partner.


Being well dressed is like any other habit. Do it first thing in the morning, consistently, before you have a chance to change your mind.

5. Don’t Feel Pressure to be “up to the minute” With Trends

Stylish people always find the middle ground. They’re up-to-date and maybe a little on-trend… without being too trendy. They’re classically dressed without appearing stuffy.

Fashion changes so fast, especially with the internet, that trying to keep up will leave you broke and exhausted. The goal should be to dress in a way that you enjoy, that makes you feel good, and ideally, doesn’t make you embarrassed of old Facebook photos 10 years from now.

There’s nothing wrong with trying new trends, and there’s an easy way to do it if you wanted to dabble. Just don’t go all-in too quickly, otherwise you run the risk of wasting lots of money and closet space.


Stick to classic designs for things like suits, dress shoes, and outerwear. Have fun experimenting with trends once your casual basics and essentials covered.

6. don’t wear athletic clothing unless yOU’re Being Active

Certain types of clothing are designed for specific purposes. Swim shorts are meant for being submerged in water. Down parkas are made to help you survive in extremely cold temperatures. Activewear is designed for sweating and ease of movement when training.

Use your clothes in the way it was meant to be used. Just like you’d only wear swim trunks and flip flops at the pool or beach, confine your activewear to the gym or when training only.

You wouldn’t wear denim and a cashmere sweater to work out, would you? Same idea.

I get that it’s easy to default to activewear because it’s comfortable and you can just throw it on without thinking too much. But if you want to learn how to be stylish, it starts with fighting those urges to be lazy and thoughtless with your outfits.

Throw on activewear only when you’re being active, plain and simple.


Try only owning enough gym clothes to get you through a week’s worth of workouts. Anything more is a waste of space.

7. dress like Yourself, not like A Specific Personality Or Celebrity

Stylish people are inspired by others, but never blindly follow.

Developing personal style is the most difficult part of being well dressed. Throwing money around to look like so-and-so is easy, but you’ll never really feel like yourself.

And besides, would you ever want to be that guy who looks like an exact clone of some celebrity or musician (who, to be honest, probably has a professional stylist on his payroll)?

screenshot of youtube video how to look like kanye west
This is a screenshot of an actual YouTube video I came across. Example of what you DON’T want to do (even if it was a celeb other than Ye).

Getting inspiration from a certain style or way of dressing is totally fine, and you can use some of the links and tips from #5 to test these looks out.

But be inspired by looks you’re drawn to for a variety of reasons—you think it looks cool, it will make your body look good, you’ll look sharp and feel and confident wearing it—not just because so-and-so wears it.


Consider cheaper alternatives, thrift store finds, and discount items until you find a style that works for you, both functionally and aesthetically. Once you nail down the style and fit you like, feel free to upgrade to better quality or nicer brands.

8. Don’t Obsess Over labels And Brands

Stylish people know that specific labels can give you general ideas about fit and quality, but won’t guarantee sartorial success. They also don’t fill up their wardrobe with pieces that are shamelessly branded.

To be even more clear: Don’t obsess over labels and brands because of perceived status or “cool factor”. Incorporate a handful of these items into your wardrobe if you really love them, sure…

But know that a truly stylish wardrobe is diversified: A good mix of high-end staples, vintage statement pieces, and affordable basics.


Avoid anything with an obvious logo, especially if you’re merely doing it for status. It’s perfectly fine to like a brand because of fit, quality, and heritage… but not just to impress your friends with a label.

9. know Your size (And Know It Can Vary Among Brands)

In some shirting brands, I wear a small, and others, a large.

I can’t recall a single time I’ve bought a clothing item from a brick and mortar store without trying it on first, especially if I’ve never worn anything from that brand before. There’s too much variation between manufacturers and fits.

The truly stylish guys know their sizing in their favorite brands, so when they’re shopping for new gear, they don’t have to think twice about size.


Know your measurements when ordering online, and try things on in stores whenever possible for the right fit.

10. Be comfortable in Your clothes

This statement is two-fold.

Stylish people take great care to make sure their clothes fit properly and are physically comfortable.

But they’re also comfortable with themselves. They’re confident.

No matter how expensive or “in” a jacket may be, if the wearer is self-conscious about a loud pattern or bold color, the look will fall to pieces. Being unsure of yourself will ruin the most important aspect of being stylish: confidence.

Stylish guys buy clothing that fits their personality and lifestyle, allowing them to walk through life confidently, with their shoulders back, chest out, and head up!

HELPER Tip #10

This is the big one. Buy clothes that you’re excited to wear and feel great in. Confidence will follow.

How Can You Look Attractive And Feel Confident?

With consistent application, following even a few of these steps will help you build a wardrobe and instill habits that will naturally result in the confidence exuded by the highly stylish individuals you admire.

So if you want to be stylish, practice these 10 habits in your everyday life and you’ll be well on your way.

How many of these habits do you recognize? Do you put these into practice? Would love to hear your thoughts in the comments below.

This article was originally written by Nate of Iron & Tweed and has since been updated by the EG team.