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!
- 10 Tips To Become Effortlessly Stylish
- 1. Dressing Well Is A Skill You Can Develop
- 2. Consider Your Personal Lifestyle and Goals
- 3. Fit Matters Most!
- 4. Buy The Nicest Quality Clothing You Can Afford
- 5. Stick to Neutral & Versatile Pieces of Clothing
- 6. Practice Wearing Your Clothing
- 7. Organize Your Closet & Do Your Clothing Maintenance In Advance
- 8. Once You Have the Basics, Experiment!
- 9. Stay Open-Minded About Style
- 10. Enjoy The Process & Have Fun With It!
- Outfit Rundown
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.
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?
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.
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.
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.
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.
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.
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.
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.
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.
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.
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
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.
Sorry Kyle, but clothing is not just clothing. It serves to express self-respect and respect for others, as well as being a morale-booster, to name but a few of its functions.
I have a dissent from, or at least a qualification to, point no. 4, “Buy The Nicest Quality Clothing You Can Afford” (3:26). For those who can infallibly judge how well they are going to like owning and wearing an item of clothing prior to buying it, this is an unquestionably sound rule. I don’t know if there are such people, but in any case I am not one of them. It has happened many times that I carefully selected an item only to find, after owning it for a while, that I did not like it as well as I thought I would. This can happen because an item does not work well with the other items of clothing that one likes to wear, because one figures out over time that the item belongs to a style that is not one’s own, because one’s taste changes, and for other reasons. Buying an item that departs from one’s past and present stylistic choices is an experiment that may or may not turn out well. This is where I find cheaper items of clothing to be useful. If the experiment turns out badly, one’s loss is small. If the experiment turns out well, one can wear the item until one has the occasion and the means to replace it with a similar one of superior quality.
Against this, one may argue that one can find high-quality items at low prices in second-hand shops. So one can, but only by luck: one cannot in general go into such a shop in search of an item of a certain sort and have a good chance of finding one, as one can do when browsing among the offerings of retailers. So, in sum, I think that cheaper items have a place in at least the early stages of any gentleman’s “style journey.”
I’m with Miles on this. Though his reason is 100% valid, I’d also like to add that certain items tend to take a lot more wear than others. Between my career (which does put me in a position to get my hands dirty at random times, and there’s a lot of sharp metal around) and large leg muscles from lifting, pants get dirty and worn quickly enough that I don’t feel bad AT ALL about grabbing something like Dockers khakis on sale for $30 for everyday wear. $200 pants wouldn’t take the wear better enough to justify going that route for my everyday use. Combined with a reasonably-priced dress shirt (that fits quite well for the price), I still look better than 98% of the people I see. Tack on a decent sport coat, and people assume I’m in charge.
That being said, when there’s a higher-quality option that I know is worth spending the extra dough, I’m all in.
Hi Miles,
Recognize your point all too well.
I found over time that some brands work well for me in fit, style, quality, and wear (and some others don’t)
Greetings,
Peter
I must disagree about finding what you want when buying second hand. I rarely have been unable to find what I am after when buying second hand. I have scored a lot of very nice things this way. Yes you have to sort thru a bunch of junk, but when you find a Zenga or Oxxford suit or something else similar for a fraction of its value it is worth the effort. The trick is to keep a list of what you are after and exercise some patience. It also helps to cultivate a good variety of second hand retailers and know what you can expect from each of them.
Thank you for advice.
Thank you for this helpful information.
We’re glad you liked it, Matthew. :)
My tips (speaking from the UK) would be: i) buy the best you can afford, it will look a lot better and most likely last longer; ii) avoid anything fashionable or flashy, the aim of a gentleman is to be invisible in his dress, never to draw attention; and iii) anything tight-fitting will probably make you look ridiculous.
Great article! In addition, remember that having confidence in yourself is just as important. Keep up the good work.
Spot on!
To me fashion style expresses not only a man’s clothes. It is more than that, how or what a man wears defines his personality. Clothing is definitely more than just wearing clothes.
Some men don’t know how to dress themselves for a first date, formal or casual occasion or some boys tend to ignore as some things are under or over budget. I must say this is the best post to get dressed in no time and on budget while considering the latest fashion tips.
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