The 5 Elements Of Timeless Style (How to Always Be Stylish)6 min read

As we start a new year, I thought it’d be the perfect time to explore the idea of timeless style.

5 Elements Of Timeless Style: How To Always Look Stylish | GENTLEMAN WITHIN

What is timeless style? I define it as always looking stylish. I believe there are a handful of elements to keep in mind and be aware of in the pursuit of timeless style.

The men who always appear effortlessly stylish are aware of or perhaps have mastered the following tenets of timeless style.

While some of these may seem basic or common sense, sometimes it’s the simplest ideas that require the most attention.

The 5 Elements Of Timeless (Men’s) Style | How To Always Look Stylish


We’ve all been there. Showing up to an event underdressed. It’s never a good look. You don’t want to feel self-conscious the whole night. I’m of the mindset to dress one level above everyone else. If you’re dressed several levels above the rest, you run the risk of looking try-hard or lacking proper etiquette.

For some events it will be difficult to come in a level up, for example when I attended StyleCon (now Menfluential) for the first time, I knew everyone else would be dressed to the nines, so I went pretty formal with a navy suit, blue shirt, silk paisley neck tie and double monkstraps for the first day. In this case, it’s fine to come in at the same level as everyone else. But in most other cases, you want to come in a level above.

Take for example, a work party or mixer, you can arrive wearing a blazer with a clean pocket square over an oxford cloth button down and clean dress shoes. More than likely you’ll be one of the few wearing a sport coat and will stand out in a good way.


In the case that you’re unsure of the dress code, I recommend reaching out to the host beforehand to ask what would be appropriate attire for the event. Once you know the details and have an idea of what others are going to be wearing, you can come in a level above them. You don’t want to show anyone up, but it’s always better to be overdressed than to be underdressed.

If the dress code is “come as you are,” then wear what you would normally wear, but one level above your standard uniform. So if you’re a jeans and t-shirt kind of guy, opt for a pair of slim chinos and a polo shirt instead. In the end, use your best judgement and dress accordingly.

The Bottom Line:
Always be aware of and take into consideration your environment when deciding how to dress. Once you’ve done that, come in one level above everyone else.


It’s been said a million times, but when it comes to good style, FIT is king.

clothing fit before and after
This often overlooked detail makes all the difference | GQ

You can wear a Prada suit for thousands of dollars, but if it doesn’t fit, you’ll look like you’re homeless. Whereas if you’re rocking a well tailored suit from H&M or Zara for a hundred bucks, you can look like a million. It’s especially important to be aware of the type of fit that most flatters your body type.

For example, if you have a more stocky build, you don’t want to go with anything too slim fitting. Skinny fits will only make you appear like the Michelin Man. A straight or more relaxed fit will be more appropriate. If you have a skinny build, then you’ll definitely want to go with a skinny fit for a more streamlined look. If you go with a relaxed if you’ll look like a kid playing dress up.

Bonus points if you can find and get to know a quality tailor.

The Bottom Line:
Form-fitting clothing flatters, it enhances, and it instantly makes a man more stylish. Nail the fit and half the battle to timeless style is already won.


More often than not, when you see a stylish guy, he’s stressing the details that most men overlook.

Maybe you’re not quite sure as to why a guy looks so damn stylish, but by becoming aware of the little details, you’ll be able to spot it more often and literally break down a guy’s style at a glance.

Maybe it’s how his pants taper towards the ankle and break cleanly over his shoes or the single, crisp cuff of his jeans. Or perhaps it’s how well he’s incorporating color or mixing and matching fabric types.

A master of details is someone who puts a price on personal presentation. He puts his best foot forward and dresses like he cares. He leaves the house not only stylish, but the best version of himself.

The Bottom Line:
Timeless style is in the details. Start paying attention to what you wear, how and, why you wear it. It makes a world of difference.

Quick note: If you’re enjoying this article on the 5 elements of timeless style, then you’ll probably find my other writing on all things men’s style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.

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Do you own a navy blazer, a well-fitting (clean) white t-shirt, and a pair of great fitting dark wash denim/jeans?

Navy Blazer Flatlays | GENTLEMAN WITHIN
Style staples like the navy blazer are versatile and timeless.

These are the top 3 menswear staples that all men can benefit from having in their wardrobes. Establish a strong foundation by curating the style staples.

The Bottom Line:
Simply put, staples are the articles of clothing that will stand the test of time and be stylish for years to come.


My winter uniform of late looks a little something like this.

When you establish a personal uniform, you will save time and brainpower. If you’re unsure of what to wear, a uniform can save the day. Think of it as your a go-to outfit of choice that you feel 100% your best-self wearing.

Do you have a closetful of denim jackets or flannel shirts? Or have you amassed a killer collection of work boots? These items are good candidates to be a part of your personal uniform. Whatever pieces you tend to gravitate towards and wear often, buy more of those pieces and wear the hell out of them.

Though it takes time to discover your personal aesthetic, it’s a worthwhile endeavor.

The Bottom Line:
Locking down a personal uniform will make deciding what to wear easier. And shopping will be a breeze since you’ll already know what to get.


Not necessarily an element of timeless style, but a bonus tip is to prepare your outfit the night before.

Try to do this consistently for one full month. This is particularly helpful if you don’t yet have a personal uniform.

A daily habit of thoughtfully preparing your outfit the night before can save you time and energy. It’s like exercising a muscle. The more you think about what you wear on a daily basis—over time—your style will improve and you’ll be one step closer to having timeless style.


So there you have it, the 5 elements of timeless style.

To recap:

  1. Dress for the occasion
  2. Wear clothes that fits
  3. Stress the details
  4. Curate the staples
  5. Establish a personal uniform

Pay attention to and adopt these 5 elements of timeless style and you’re well on your way to always looking stylish. Who needs trends anyway?

Onto you. Which of these do you need to work on?

Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.


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  1. Dennis says

    Wonderful instructions for getting dressed up for the occasions. Very helpful post. Bottom lines take the credit. Thank you for sharing the post.

    • Khoi Nguyen says

      Dennis, appreciate the message and glad that it was helpful for you. Cheers!

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