10 Secrets of Effortlessly Stylish Men

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Certain men almost always look great, no matter when you see them. You might think of Steve McQueen, Cary Grant, Ryan Gosling, or Frank Sinatra as effortlessly stylish, for example. What’s more: it’s absolutely possible for you to create that kind of visual charisma without spending a ton of money or having your own personal stylist–just by learning these 10 style secrets!

Many of these effortlessly stylish men dressed themselves and made their style an extension of their identity. And they did this by following a chain of principles, which you can replicate in your own life. That is to say, you, too, can find your own signature style, which will serve as an extension of yourself.

10 Tips To Become Effortlessly Stylish

1. Dressing Well Is A Skill You Can Develop

When you first start out on your style journey, you might have a vague idea of what you want to achieve, but might be overwhelmed by the number of options and information made available to you. As oxymoronic as it might sound, the more you study how to dress well and make clear, deliberate decisions about how you look, the easier it will come to you. It’s not a magical trait that you are or are not born with.

The more you gain knowledge, the more confident you’ll be with your choices.

Like training a muscle, the more information you have on color theory, pattern matching, pattern meshing, and the historical understanding of formality, the better you’ll understand how to naturally put together a great outfit. Once you understand the foundation of how to be well-dressed within the principles of the classic style, you’ll start to develop an appreciation and a fondness for certain articles of clothing. 

2. Consider Your Personal Lifestyle and Goals

Once you understand what’s classic and timeless, you need to assess then what kind of clothing you’d actually include in your day-to-day life. And while owning a bunch of three-piece bespoke suits is nice, it won’t help much if you, for example, are a warehouse worker who rarely gets an opportunity to wear them. However, you could also get a lot of mileage out of something like Red Wing boots in this scenario.

It’s also important to understand why you’re dressing well in the first place. Are you looking to get an edge at work and want to present yourself in the most professional way possible? Are you doing it because it makes you feel good, and it’s a personal statement as to how you respect others? Or is it a step on your journey in self-improvement?

Assess what type of outfits you’d most likely wear on a daily basis.

Once you have these points locked down, it’s important to then create a checklist of the things that you want to add to your wardrobe that will be the most beneficial to you. Doing this prevents impulse buying and ensures that you get the lowest cost per wear on what you decide to purchase.

3. Fit Matters Most!

You can own the most high-quality clothing in the world, but if it doesn’t fit right, something will always look off about your appearance, almost as if you don’t look at home in your own clothing. An incorrect fit can throw off your body’s proportions and give the appearance that you’re either shorter, heavier, taller, or thinner than you actually are. This will kill any opportunity you have to look effortlessly cool right out of the gate.

We can’t stress this enough – having the right fit is important.

Men will often choose clothing that is far too big for them because they want to appear broader than they actually are, or they want to be the most comfortable. And while skinny fitting or clothing can be just as unflattering, understanding what works best for your body type will save you a lot of frustration and heartache. Also, while the modern style plastered on billboards or online marketing content can be tempting to pursue, it just won’t work for every man, so be secure in styles that flatter you best.

4. Buy The Nicest Quality Clothing You Can Afford

Once you get the fit down, you can earn bonus points by picking up clothing of the nicest materials and construction. One of the best examples of this is with dress shoes. Having a shoe with a blank stitch or Goodyear welt along with great calfskin will always be more eye-catching as opposed to having a shoe that is poorly, made which will fall apart in around a year. 

Quality clothing not only looks nicer in subtle ways; it also lasts longer and will appear more lived in. Having a shoe patina and cork molding that’s unique to you, for example, will make them feel more lived in and almost like a second skin every time you wear them.

Shoes that are made with the highest quality doesn’t just look nice, they will also last longer.

This technique will also help you create your own uniform as you’ll start to have your own signature articles of clothing every time you get dressed. Certain construction methods will also enhance fit in ways that a cheaper product can never replicate. The canvas in a jacket, for example,  will mold to your body and will drape better over time as opposed to a fused jacket.

While you should never spend above your means, it’s important to remember that you should focus on fewer pieces of greater quality, rather than many things of lower quality, which are probably going to just get discarded anyway.

Less is more.

These also aren’t necessarily branded clothes as most designers have inferior construction methods and sell mostly off of their own name recognition. Having an eye for what constitutes a well-made piece of clothing will help you both save money and stay away from overly logoed clothing, which makes you look like you’re just trying too hard.

5. Stick to Neutral & Versatile Pieces of Clothing

When creating your foundational wardrobe, try to stick to neutral and versatile pieces of clothing. You also want to pick up clothing that will be able to be paired with as many outfits as possible. While a white dress shirt and a navy blazer aren’t the most exciting things on their own, they can easily be included with other outfits and other accessories to create a more bold statement, if you so choose.

While this green jacket isn’t necessarily neutral, it can still be a versatile piece when paired with more subdued garments.

Knowing that everything that you own is interchangeable saves you the stress from having to match if you’re not one who likes to plan outfits. And nothing screams effortless more than putting together a clean outfit in a matter of seconds.

This only works if you choose articles of clothing that are neutral by design. Having a wardrobe primarily consisting of white, blue, navy, gray, brown, and khaki is both masculine and a refined choice. And these are all neutral colors that, for the most part, can always go together.

6. Practice Wearing Your Clothing

When you start to get nicer clothing, you’ll be stepping out of your comfort zone and might not feel quite yet comfortable in wearing them. The best way to fix this is to get into the habit of wearing them. Whether it’s around the house or when out running errands, just to get into the habit of doing them so that when it’s time to wear them, you can do so effortlessly at work or at an event.

Once you get comfortable in your style, you’ll be as confident as these three.

While you should always take care of your clothing, it’s important not to baby them and be overly paranoid about ruining your clothes. For example, when Sean Connery was cast as James Bond, he was advised to get a suit made on Savile Row and wear it at all times. While Connery expressed that he didn’t feel like himself at first, the more he wore it, the more it became an extension of himself.

7. Organize Your Closet & Do Your Clothing Maintenance In Advance

Even if your clothing is versatile, it won’t matter if it’s a wrinkled mess or if you can’t find it five minutes before you have to head out of the door. Being proactive about how you store and care for your clothing will save you a lot of time and stress in the long run.

Keep your closet organized and do any maintenance necessary in advance.

You can also practice habits like setting out your clothes the night before if you’re not much of a morning person. Preparation eases the mind, and it makes you more confident that things will go smoothly, which will give you the demeanor of someone who’s in control without trying too hard.

8. Once You Have the Basics, Experiment!

Don’t be afraid to experiment once you have the basics. Once you have all of your essentials covered, now it’s time to start fine-tuning your style and finding your personal flair. Ask yourself if there’s a particular style you prefer over another–for example, double-breasted jackets over single-breasted jackets, or bow ties over neckties. This is where you can start to fine-tune those style differences.

Don’t be afraid to experiment,

Try to go for brighter and bolder colors than you would normally choose. Instead of buying something in the navy, try buying something in royal blue. Throughout this process, you’ll find your own quirks that will help you differentiate yourself within the guidelines of classic men’s style and help you develop a style that looks best to your personality. This will make you even more comfortable in your outfits, and that ease will give off a laid-back elegance, which will attract other people to you.

9. Stay Open-Minded About Style

There isn’t just one right way to be stylish. At this point, you might find yourself feeling like you’re on a bit of a plateau on your style journey. To avoid feeling like your style is stale and stagnant, it’s important to follow people whose style you respect. Following them can give you outfit combinations that maybe you didn’t think of, and this can also expand your repertoire with a second opinion.

Follow people whose style you respect. Like these three, perhaps?

Having a community of like-minded people can help your journey feel less lonely. The beauty of the internet is that it connects like-minded people around the world who otherwise would not have met. While your style journey might only consist of you and your personal life, having a group of like-minded people can help keep you held accountable and motivated.

10. Enjoy The Process & Have Fun With It!

At the end of the day, clothing is still just clothing. While it can make a difference in your day-to-day life, it’s important to not take it so seriously so that the process isn’t fun anymore. Don’t be afraid to make mistakes, as everyone has at one point. Realize that it’s not the end of the world, and don’t be afraid to laugh at yourself a little bit.

Young Raphael in a white suit with a Mao collar–trendy at the time, not so impressive today!

This live and let live attitude will exude off of you and put people at ease, and instead, will make you seem smoother and cooler in how you present yourself.

What do you think makes up an effortless style, and do you practice it? We’re curious, and we’d like for you to share it in the comments!

Outfit Rundown

Kyle wearing a grey sport coat over a gray turtleneck, paired with dark wash jeans and some really dark green boots.

Fort Belvedere

Burgundy Silk Wool Pocket Square with Paisley in Beige, Blue, Green and Pink and beige shoestring edge – Fort Belvedere

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Fort Belvedere

Caramel and Dark Burgundy Shadow Stripe Ribbed Socks Fil d’Ecosse Cotton – Fort Belvedere

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I’m wearing a dark grey sportcoat with blue and gray checks over the top, a burgundy-based Fort Belvedere pocket square with some unique blue and green flecks of color inside.

I also have on a Merino wool, gray turtleneck sweater, dark wash jeans, some really dark green boots, and a pair of gold and burgundy shadow stripe socks also from Fort Belvedere.

For accessories like the pocket square and socks you see today, check out the Fort Belvedere shop.