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

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

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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.


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. 

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.

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.

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.

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.


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

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.

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.

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.


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.

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

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