Men’s Style Guide: Clothing That Will Never Go out Of Style

men's fashion style guide

There is always going to be the latest ‘something’ to hit the market, but what really establishes a man’s iconic style, is following the men’s style guide of timeless items. Say your best friend just dropped all sorts of cash on the latest pair of Nike Jordans. They look so fresh and you’re wondering if you should get yourself a pair. We say, maybe not. And here’s why. Fad styles, like fad diets, never last. It is not about affordability, either. It is simply a matter of what makes you look good yesterday, today, and twenty years from now. We have compiled a list to guide you to timeless, classic pieces today’s savvy man needs to have. Embrace your personal flare, but be sure these ten items are always included.


Whenever you make a purchase through links on this page we make a small commission from our affiliate partners. Learn more


The Incredibly Simple White Tee Shirt

Calvin Klein Men's Cotton Classics Crew Neck T-Shirt, White, Medium

Clean, simple, flawless. What man doesn’t want to be described this way? Whether you are cruising down the coast on your motorcycle or meeting up with friends for summertime happy hour, the white tee shirt just works.

Keep it fitted, keep it white, and it will never let you down. The white tee shirt is the foundation to almost any outfit, so do yourself a favor and buy several…along with some bleach. White tee shirts can range from a few dollars to over $400 (thank you, Tom Ford). Just keep in mind, it is white, so unless you can offer it immaculate care, it is okay to buy cheaper and often.

A Great Pair Of Jeans

Levi's Men's 505 Regular Fit-Jeans, Dark Stonewash, 29x34

Good denim is truly the workhorse of any man’s wardrobe. A good pair of jeans will last you for years if properly taken care (wash inside out on a cold, gentle cycle; line dry).

Talk about effortless. The fashion potentials for jeans are nearly endless and, by no coincidence, go splendidly with almost all the other items in this style guide (the navy suit being the only exception). With jeans, you will want to find a fitted pair in a darker wash, you could even try selvage for its durability. Buy the highest quality you can afford.

Jeans can be dressed up, dressed down, cuffed, belted, are casual Friday appropriate or worn to your favorite sporting event. We know the ripped, distressed look is still going strong, but remember we are opting for timeless here. Get yourself a pair of clean, no-fuss jeans, your future self will thank you. Because the best part is, jeans are a wardrobe staple that get better with time as you wear them in – similar to the next item on our list, the black leather jacket.

The Black Leather Jacket

Tommy Hilfiger Men's Smooth Lamb Touch Faux Leather Unfilled Bomber, Black, L

While there are several styles out there, the most classic of leather jackets are the moto, racer and bomber jackets. They span decades without ever losing their allure and taste. As with other timeless pieces, these leather jackets work on all body types and give their wearer an edgy look without being too tough.

Find one that fits and zips up effortlessly and is made of real leather – synthetics may look the part, but they will also fall apart. Because of the nature of leather, it will distress over time, but do take care of your leather jacket. There are easy-to-find guides on how to do this all over the internet, apply their wisdom accordingly. Take care of your leather jacket and you will see how it returns the favor.

A Must have Mens Watch

Invicta Men's 8928OB Pro Diver Gold Stainless Steel Two-Tone Automatic Watch

There is something about a watch that brings maturity to your style. It can only improve your outfit.

The watch is where you can add a bit more of your personal style to this ageless accessory. Just don’t go overboard. Analogue is more classic; but there is certainly room for a tasteful digital.

You can personalize your signature watch in several ways: an analog watch with cobalt face, brown leather strap, and white gold finishings will look drastically different from an all matte black digital; yet both can look sophisticated and appropriate. A white or cream face with a cognac leather strap can look especially sharp with your navy suit for a color contrast without looking disjointed.

Similar to the leather jacket, go for real leather. The durability is worth it and although may be an investment up front, will save you time and money down the road from needing to replace the strap every few years. While we may be a little bias towards leather (the timelessness makes it a tough competition), there are other straps that can look just as smart like stainless steel or fine mesh canvas (harder to pull off, but we won’t exclude it).

Converse Chuck Taylors

Converse Men's Chuck Taylor All Star Slip Sneaker, White/Black, 8 M US

Of anything on this men’s style guide, Converse Chuck Taylors are not only timeless, but no one is too young or too old to wear them. Talk about ultimate versatility. A pair of Chucks can take you through every season of life.

No matter your favorite color, you can find a Chuck in it. Of course, we are thinking more along the lines of the iconic black and white; but one could argue other colors work because this shoe really knows no limits.

We have seen them make their debut as a basketball shoe and trend through as a wedding shoe (for both bride and groom), the rock band shoe, the shoe of weight lifters, and many other art and subcultural standards. Whatever your reason for wearing this shoe – we love them simply for a classic casual look – having a pair of Chuck Taylors in your repertoire will always be a smart choice.


Ray-Ban RB3519 Aviator Sunglasses, Matte Black/Polarized Green, 59 mm

Sunglasses are an item where it may be tempting to let personal style shine, but there is one specific pair of sunglasses that will always look right. Whether you’re in your twenties or sixties, the wayfarer sunglasses are the type to go for. The frame is simple while still being distinguished.

Depending on the shape of your face, wayfarer sunglasses vary subtly in their frames to compliment whoever is wearing them.

If wayfarer just is not your game, consider its simplicity and structure and opt for a pair of sunglasses with a similar presentation.

We won’t neglect the aviators here, as they have survived nearly one hundred years now. These sunglasses are cool, there is no denying that. While they may not be universally wearable on every man, if you can pull them off, then you definitely have your lifelong signature look.

The Stylish Navy Suit

Where sexy and sophistication meet for a perfect ensemble. What man doesn’t look impeccable in a well-fitting suit?

Oh, and feel free to rock this with your wayfarers and Chuck Taylors, we won’t mind.

There are certainly ways a suit of any kind can be trendy. Buttons, stitching, pleating, lapel width, etc. But if you are looking for that classic suit that will look good no matter the decade, stick to minimalism with your navy suit. Medium width lapel, no pleating, single-breasted, blended stitching, and you have got yourself a suit that will last a lifetime.

The Henley Shirt: A Winning Casual Ensemble

H2H Mens Casual Slim Fit Henley Shirts with Bound Pocket of Waffle Cotton HEATHERNAVY US L/Asia XL (KMTTL062)

Check out this Mens Casual Slim Fit Henley Shirts

The Henley shirt is a man’s go-to shirt for comfortable, casual fashion. The few buttons along the placket give it a nice variance from a plain tee shirt, without the more formal look of the collar on a polo. Find a Henley you like and get it in a few neutral colors: beige, heathered navy or olive, dark gray, even black. Similar to the white tee shirt, a Henley offers its wearer practical functionality along with easy style. The Henley comes in short, three quarter, and long sleeve. A beige long sleeve Henley with your dark wash jeans will look well put together while keeping you incredibly comfortable.

The Blazer: A Key to Formal Dressing

Goodthreads Men's Standard-Fit Linen Blazer, Denim, Large

The blazer, thanks to Ralph Lauren, has made its way onto our men’s style guide as an iconic, widely accepted essential. This is one of those pieces that instantly elevates whatever you are wearing.

Every man needs this in his closet because it fits in that in-between occasion that does not require a suit, but when you really should wear a jacket. As with most of the essentials in this guide, keep your blazer simple. The fewer the details, the broader the range. The blazer will take you from your Friday dinner party to your casual weekend getaway.

The Trench Coat

Mordenmiss Men's Wool Single Breasted Winter Trench Jacket Woolen Pea Coat Style 1 Black XL

No longer reserved just for British officers, the trench coat has kept dapper men dry and stylish for over one hundred years. It wears neatly over your suit to the office just as it does over a Henley, cuffed blue jeans, and white sneakers on the weekend. All of its signature markings – epaulettes, cuff straps, storm flap, and more – are as resilient today as they were for the military in 1895, and will be for the next century. The honey or camel color is as classic as it is versatile, but don’t let that stop you from considering a trench coat in black or navy.

Are You A Man Of Timeless Style?

Yves Saint Laurent once said, “Fashion fades; style is eternal,” and we agree.

The items in this men’s style guide transcend time, season, and trends. Sure, you can add your pop of color and bold pattern to the mix, but we guarantee that these essentials will see you through the next several decades. Many of them may even become family heirlooms passed down to the next generation and beyond. That great leather jacket, luxury watch, or classic sunglasses, will all be just as desirable fifty years from now as they are today.

For each of these items, as mentioned before, buy the highest quality you can afford. But do get them. You are all about looking your best and you can see how easy the iconic, classic men have done it for years. It i no hidden secret. Looking effortless, transcendent of time, is really just simplicity at its finest.



Should You Wear a Tie to Work? Here Are 9 Reasons To Why

How Often Should You Wash Business Shirts and Work Clothes?

Men’s Dress Watches – 9 Questions To Ask Before Buying

Where to Go Swimming With Whale Sharks Up Close And Personal

Best Places to Go Bungee Jumping In the US That’s So Amazing

Does Airbnb Rent Apartments Long Term? What To Know Before Renting

Recent Posts