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men style, men's classic style

9 Timeless Staples of Men’s Classic Style

Over time, there have been certain trends in men’s fashion that have turned into staples. We call these men’s classic style, or “classics,” rather, that are timeless. These style pieces are iconic and can be mixed with current trends at all times. 


Because of the “timeless” nature of the men’s classic style, every man should have these as staples in their wardrobe.


So, if you’re looking to class up your look, add an air of sophistication to your style, or if you’re looking for a friend, you can’t go wrong with a classic style. Keep reading for our must have staples to complete a men’s classic style look.

Men's Classic Style, leather jacket

Men’s Classic Style – Get the Look with These Iconic Staples

Do wear a leather jacket!

First and foremost, you will nail the men’s classic style every time with a leather jacket. You will never go wrong with a black leather jacket for men. It’s a must have style piece every man must have in his wardrobe.


A leather jacket might be one pick many stare at but it is a timeless piece of fashion. Invest in one and it could last decades.


It gels well with most occasions and works around all silhouettes and styles of dressing up. Leather jackets are classics but there are a few tips that make them suit you better when you plan on flaunting one.


Leather Jacket Style Tips

Never over accessorize. Overdoing what you wear with a classic jacket will only demean the glam factor involved. Keep your accessories minimal and see how this ups your fashion game.


Always be sure the jacket fits properly. Nothing will kill that classic style more than a style piece that’s too big, too small, or too bulky.

messenger bag, Men's Classic Style

Say, “Yes!” to the man bag.

It’s funny how many guys are terrified of the man bag. It is by far a huge staple of men’s classic style. Plus, it serves a practical purpose that most men can’t go without serving once they start using one.


From bling to leatherette, there are tons of styles available. We have come far away from the time Joey modeled the Man Bag on Friends, after all. 


Man Bag Style Tips

Leather and rugged. The more worn and rugged a man bag looks, the more classic it becomes. Think, finding your grandfather’s bag. It never goes out of style.

nautical stripes, men's classic style

Sail off in nautical stripes!

Nautical stripes are back—or maybe, they never went away because they are timeless! When it comes to men’s classic style, you can’t go wrong with this option.


This spring fashion season has marked the popularity of the stripes again. It could be in any hue, any style, any thickness but what it will do is lend some jazz to your look.


Style Tips for Nautical Stripes

Don’t be afraid to accessorize with stripes. Nautical stripes have made their way into wallets and even socks and shoes. Of course, stripes help you look slim too—perhaps that is why this is a trend men refuse to kill. 

Men's blazer, sport coat, men's classic style

Add a sport coat to your wardrobe.

You can’t go wrong in a sport coat. Whether you’re dressing for dinner, work, shopping, pr travel, a sport coat is a staple that will add classic sophistication to any man’s look. It will never go out of style and always come in handy.


Sport Coat Style Tips

Color and weight correlate with seasons. When shopping for a sport coat do keep in mind that lighter colors and weights are generally worn in spring and summer while darker and heavier weights are worn in fall and winter. 

men's leather belt, men's classic style

The right belt always works.

As a man, you will find it worthwhile to invest in a good quality belt. A good belt is key for achieving the men’s classic style. Whether it’s worn with denim or slacks, a belt is not just functional, it’s stylish too.


Generally, a good belt can be used for years, decades even, So, it’s worth spending the money on quality over quantity when it comes to this accessory.


Style Tips for Belts

Go in for leather and stick to basic colors such as tan or black. Do check out the fit of the belt first before deciding on one. Also, ensure that you get the right size.


A smaller-sized belt will not allow you to be comfortable. Similarly getting one size up also leaves too much extra belt hanging out and all over. Generally, the less extravagant your belt is, the better fashion sense it ends up making.

Oxford Shoes, men's classic style

Oxford shoes make everything right.

No matter how many sneakers you buy or how many sports shoes you have, invest in one good pair of formal shoes. Oxfords are a men’s classic style pick and work well with all sorts of formal outfits.


From a job interview to a wedding brunch, you can wear them on umpteen occasions. These shoes need good maintenance though and thus, you must ensure that you store them tidily.


Style Tips for Oxford Shoes

Keep the color simple but don’t be afraid to go for a fancy design. Neutral colors will work with just about anything and the contrast of fancy Oxfords with casual attire creates a smart look of contrast for a classic look.

watch, men's classic style

Do get a statement watch.

A statement watch is another staple of men’s classic style that is as functional as it is fashionable. Buy a weighty watch that gels with your personality and goes with your work profile.


Since men generally do not go overboard with accessories, the right watch makes a whole lot of difference. Check up on the latest trends and pick a watch that is not too flashy but one that has an understated yet eye-catching style.


Depending on your work profile and style sensibility, you can pick a watch that stands for your personality.


Style Tips for Statement Watches

Size should match Braun and style should match function. If you’re on the smaller side, you don’t want to wear a watch that’s too bulky. The same applies to larger men. And always remember the function for the look. 


You wouldn’t wear a diving watch to a business dinner or a sleek Rolex to dive. So keep that in mind when you’re shopping.

wayfarers, men's classic style

Wayfarers never go out of style, like, ever.

Everyone needs a pair of sunglasses. You absolutely can never, ever, go wrong with a classic pair of Wayfarers. These sunglasses have been in style since James Dean stole the hearts of our grandmothers in the 1950s. And when it comes to men’s classic style, they’re here to stay.


Wayfarer Style Tips

You can choose polarized lenses for a more edgy look, or if you need them for sporting purposes. However, classic black is generally the more common choice and can be worn with anything from denim to tuxedos.


Don’t forget the hair!

Even though your hairstyle cannot be called an accessory, it still is part of fashion trends. And if you’re really going for a men’s classic style, you have to have the right hair. 


A good trim is one classic trend that never will fade away from the book called men’s fashion. Even if you play around with the hair shade, play with undertones and darker shades. Loud styles never end up on the classics’ list but can be used if you’re going for more of a classic look with an edge.


Summing Up

Whether you’re shopping for yourself, a friend, or for Father’s Day, the clever way to build up the stylish element in your wardrobe is to follow fashion trends but never aping them blindly. Trust classic picks to invest in pieces that will last you a very long time to come. 


Men’s fashion is evolving with time, revealing shades not many expected of the same. However, how you dress up and choose to “be fashionable” is completely a personal choice. Remember, men’s fashion is also about comfort as it is about style or trends.


When it comes to men’s classic style, don’t be afraid to spend on quality because the pieces you choose will stay in style basically as long as you’re alive so, it’s worth the investment as your items will last much longer.


Christa Thompson

Christa Thompson is the Founder and Chief Editor of The Fairytale Traveler. She started traveling the world in 2003 when she attended a summer abroad study at the University of Cambridge in England. Since then, her wanderlust has been fierce. Her three passions in life are her son, traveling, and being creative. The Fairytale Traveler brand gives Christa the opportunity to do all of these things and to live intentionally every day. "It's never too late to believe in what you love and to pursue your dreams." -Christa Thompson

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