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15 Men’s Fashion, Style And Dress Tips For The Clueless Guy

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Clothes and Accessories - Men Fashion, Style

Begin your creative journey into the world of men’s fashion and style with your very own beginner’s guide.

Men’s fashion, style and way of dress is more important today than it has ever been, yet there are countless guys walking around absolutely clueless about men’s style. Admittedly, I was one of the most clueless.

As an ambitious man hell-bent on succeeding at everything you do, possibly a man who practices the TooManly lifestyle, the ultimate goal with clothes is to look your prime at all times so as to improve your chances at winning in life. You want to avoid having a fashionably inept wardrobe that jeopardizes your social status and career prospects.

While it can seem like there’s a lot to know about good style (there is!), looking sharper than 99% of other guys is actually a lot simpler than you think and only requires doing the little things right. Boost your self-esteem with our comprehensive beginner’s guide on men’s fashion, style and dressing.

1 Keep It Simple, Don’t Overthink Fashion Style

Man wearing simple-looking denim outfit

Developing good style can be easy. Simply having well fitting clothes is all it takes sometimes to look more stylish than most men.

We all want to separate ourselves from the pack one way or another, but unfortunately, many guys try too hard by dressing outlandishly or even slobbish. What they don’t realize is that simply having the fit of your clothes on point is all it takes sometimes to stand out and look stylish.

“Keep it simple” doesn’t mean dressing plainly or not doing anything that may garner attention. It means not overthinking things.

Good style doesn’t have to be difficult or expensive. The white t-shirt and jeans combination, for example, is one of the most iconic men’s fashion styles because it’s simple, comfortable, budget-friendly, and appealing when everything is tidy and fits well.

2 Focus On Fit In Addition To Comfort

Man wearing a simple outfit

It’s easy to find clothes that look and fit good and are comfortable to wear. You don’t have to sacrifice one for the other.

Speaking of fit, many guys wear clothes that are either too small or too large for them, ill-fitting clothes that often undermines their masculine physique and makes them look less manly.

Wearing attire that accentuates the positive aspects of your body can instantaneously make you more attractive to women, more admired by your peers, and more confident in your abilities.

Fit is one of the most important men fashion, style and dress concepts to understand and master. While fitted clothes may feel a bit unfamiliar at first, especially if you’re used to baggy shirts and jeans, don’t confuse that feeling with discomfort. Unfamiliar is not uncomfortable — you’re just not used to it yet.

High-waisted jeans like the ones Simon Cowell wears are a definite no-no, as are skater slouches that show your boxers. How are sagging pants look is still in vogue in the 21st century?

It’s easy to find clothes that not only look good and fit good, but are also comfortable to wear and allow you to move freely. You don’t have to sacrifice one for the other.

3 Layer Your Clothes For A More Interesting Look

Layering clothes make outfits more interesting

Layering doesn’t have to be difficult. Sometimes, all you need is a well-fitting blazer or sweater on top of a simple shirt to smarten your.

There is nothing wrong with wearing a plain grey sweater and jeans — it’s a fine and simple casual style — but one way you can achieve an even more stylish look is to add some layers.

Many guys get a little intimidated by layering because they don’t know how to match clothes all that well, but it’s actually not rocket science and can be done with very simple clothes.

Want to look more sophisticated? Well, you don’t have to suit-up. Sometimes, all that is needed is a well-fitting blazer or sweater on top of a simple shirt to smarten your casual or professional look.

In the men fashion style world, this is called smart casual. The goal is to have a neat, conventional, yet relatively informal style for the occasion.

It doesn’t just have to be one layer — you can wear two, three, even four layers at a time — so feel free to play around!

4 Jeans Aren’t The Only Pant Type In The World

Men Wearing Chino Pants

Jeans are great and stylish, but they are not your only option for legwear. Add some chino pants to your collection.

Jeans are great, stylish and convenient, but they all look kinda the same, don’t you think? Jeans should not be your only option when it comes to casual trousers and legwear.

Most outfits that can be pulled off with your favorite pair of jeans can also be pulled off with some quality chino pants, so adding a pair or two to your trouser wardrobe can easily double or even triple the number of styles you can create.

You can play it safe and go with traditional colors like camel or grey, but don’t be afraid to also add a colored pair like burgundy or army-green (vibrant colors like lime-green and fire-engine red can be a bit much, though) to change things up a bit.

Wearing color below the waist is something few men do, so you will definitely standout.

5 Color Match Your Belt And Shoes

Color-matching belt and Shoes

Color matching your belt with your shoes is a basic dress code. Black with black, brown with brown.

Such a simple touch, but nothing puts a look more out of joint than an extremely contrasting combination. It’s just to bad that, unlike women, most men find matching to be a real pain.

Color matching your belt with your shoes is a basic but important men’s fashion, style and dressing rule, and guess what guys? It’s not that hard to master.

Going back to our first tip on keeping things simple, the key is not to overthink style. Just remember a few basic rules when matching: Brown shoes? Brown belt. Black shoes? Black shoes. Make sure there is a match regardless of the color you choose.

The shades don’t have to be identical, but the general colors do. However, the more contrast there is between your belt strap, your shoes, and other fashion accessories like your bag and hat, the less stylish you will look. Try to match the colors as closely as possible.

6 Have A Quality Wallet For Your Valuables

leather wallet holding cards, money

Investing in a quality wallet will keep your money secure while making you look more mature.

They say there’s more important things in the world than money, and that’s certainly true. Your wallet is one of those things, so you better make sure it’s high quality.

A ripped, scratched wallet is more likely to have you losing your cash than winning admiring glances. If you have been carrying around a piece made from fake leather, synthetic fibers or — heaven forbid — Velcro in any shape or form, it’s time to invest in a decent wallet that does a better job of keeping your money secure while making you look good.

Wallets come in different shapes, sizes, styles and form, so there is definitely one for you. For guys who like to travel a light, a simple card holder is the way to go; if you tend to fumble credit cards and spare change onto the floor when rifling around for something, a zip wallet is a sure bet.

For those men who value a classic look above all else, there is no beating a quality leather flip wallet, possibly one with a zip compartment for securing loose items.

7 Consider A Man Bag For Better Practicality

Man Bag - Men Fashion, Style

Roomier and more practical than a wallet, the man bag is back in style. Do you have one?

If you are set in your ways and possibly even a bit old-school, the thought of owning a man bag might give you a brain aneurysm. But times have changed, and having one can be a fantastic addition to your wardrobe.

Although generally small and compact in size, and often referred to as a “man purse” (“murse” for short), man bags actually come in all sizes and shapes, ranging from something as a small as, well, a large woman’s purse to something as big as a messenger bag. They tend to have a masculine or a more unisex appearance that is more streamlined than a backpack and less bulky than a briefcase.

Weighing down your pockets with keys, wallet and phone damages the material of your trousers, nor is it exactly comfortable, so a stylish bag might just be what the fashion doctor ordered.

And don’t worry about not looking cool — man bags are not going out of style anytime soon.

8 Say No To Graphic Tees, But Yes To Patterns

Pattern Shirt - Men Fashion, Style

Printed and patterned shirts are acceptable and very popular contemporary men’s fashion that can be a stylish addition to your outfit.

Graphic t-shirts used to be popular back in the nineties, but they are no longer a stylish way of dress in the 21st century. They don’t make you look funny, edgy or original, nor do they make you stand out from the preponderance of men who still wear them.

If anything, wearing graphic tees makes people think you are a kid, so leave the graphic tees in the 90s, where they belong.

Try patterns and printed clothing instead. Not only are they a very popular contemporary men’s fashion style, but they can also look very good.

For an even more mature look, find some casual button-downs or polo shirts. Anything with a collar and some buttons in the front will flatter most body types better than any t-shirt.

9 Class Up Your Footwear, The Ladies Are Looking

Dress Shoes - Men Fashion, Style

Wearing a pair of black or brown leather shoes can instantly give you a confident and sophisticated look.

People notice your footwear, and I can’t tell you how many compliments I get on my shoes from women, even though I didn’t spend hundreds on my rather small collection. Your dirty, beat-up sneakers and running shoes, on the other hand, will ruin an any outfit and eviscerate what little style credibility you might have.

While having sneakers as your daily footwear can work, there are simply better options out there. Wearing a pair of black or brown leather shoes (boots, casual dress shoes, etc.), for instance, can instantly give you the confident and sophisticated look women seem to crave.

So donate your old sneakers or use them for gardening and any other everyday household chore. Try to keep your gym shoes for the gym only, and nothing else.

10 Have A Watch, They Are Still Stylish And Useful

Watch - Men Fashion, Style

Every man should own at least one good watch that compliments the appearance of his entire outfit.

Young Millennial men today see watches as dated, old-fashioned, and even obsolete gadgets of their grandfather’s generation, thinking something along the lines of “my smartphone tells me the time, so why would I need a wristwatch?”

Well, for starters, they are timeless (pun intended)!

Wearing a watch is also a simple way to bolster any look, and remains the most convenient way to check the time.

Great men like Bill Gates, Bono, Elon Musk, Warren Buffet, and Pope Francis all still wear traditional analog watches, and it’s not necessarily because they are old farts.

Every man should have at least one good watch, and by “good watch” I mean one that is reliable and compliments the appearance of your entire outfit. It doesn’t have to be a 56mm piece that your shirt cuff can’t even go around it, or something with cubic zirconias all around it.

Plastic digital watches, for instance, have their place, but they have no business being around a nicely-tailored suit.

11 Ties Are Timeless

Man necktie - Men Fashion, Style

The age-old necktie is a fashion item that won’t go out style anytime soon.

Men fashion style trends come and go, but men’s fashion has changed very little in the last century. The necktie is one of those fashion pieces that continues to be a must have in every man’s wardrobe, and the practice of wearing one hasn’t changed much in centuries.

Accessorizing a shirt, whether casual or smart, with a tie can prove to be a big boost on your fashion-consciousness. Just make sure the tie is touching your belt, as going any higher could look disorientated.

You also don’t want go too wide (old-school style) or too narrow (super slim-fit ties).

12 Wear A Scarf In Any Weather, Warm Or Cold

Wear scarf - Men Fashion Style

Scarfs have become one of the best fashion accessories for men, making it easy to find a style for any weather.

The scarf has risen in polarity to become one of the best fashion accessories for men everywhere, even serving as an alternative to the necktie in some situations. Yes, they help keep you warm, but these days, people don’t only wear them when it’s cold outside!

The proliferation of lightweight materials and summery prints in recent decades means you can find a slew of unique scarfs that come in different sizes and lengths to suit any weather. For example, when wearing your favorite shirt, choose a short scarf to adorn your neck like you would a tie.

There is nothing like a bit of opera-going sophistication to add to your ensemble, but wearing a scarf in warmer weather can be a tricky one to get right. As someone new to men’s fashion and style, start with something understated and wear it draped around your neck rather than tied.

13 Be Your Own Stylist, Don’t Follow Trends

Clothes Shopping - Men Fashion Style

Fashion trends come and go, but you want a look that’s timeless. Use trends as a fun inspiration, at best.fwallet

What is trending in men’s fashion? Answer: who cares! A better question to ask is “how does the way I dress make me look and feel?”

Don’t pursue ‎men’s fashion trends just because they’re “in”. Trends are generally a way for companies to separate style illiterates from their money, and you will no longer be a clueless style illiterate after digesting every single one of our men’s fashion, style and dress tips.

If you’re just a regular guy looking to become a better dresser, knowing what’s trendy probably won’t help you much. So keep your look timeless, and use trends only as a fun inspiration if they appeal to your existing sense of style.

14 Iron Your Clothes Like Your Mom Thought You

Man Ironing - Men Fashion, Style

A bad iron can make any outfit look bad. Every ,am should have a good iron and ironing board.

What’s the point of having well-fitting, color matched clothes if they look like they’ve been balled up and tossed around like a football?

I’m pretty sure most Millennials don’t use the clothes iron for a myriad of reasons, includes a lack of time or sheer laziness, a nonchalance towards fashion, and even the fear of being burnt. It also so happens that most fabrics today don’t need ironing.

Yes, ironing is a chore, but a bad iron can make wrinkled clothes even worse. If you don’t already have a quality iron and ironing board, it’s time you made your mother proud and got a set.

15 Stop Dressing Like A Boy, Dress Like A Man

dress mature - Men fashion style tips

As a prime man, your goal is to look mature, which doesn’t necessarily mean ‘old’.

Many men approach casual style and fashion from the wrong angle. They aim to look youthful instead of mature, and the end result is almost never good.

Maturity is an attractive quality in men and is what separates real men from boys. Maturity oozes masculinity and commands respect.

Having a mature look doesn’t mean dressing like your dad or an old person. Rather, it means not portraying yourself as a teenager when you’re not one.

Want to be treated better? Want more attention from women? Want the people around you to think you are a mature adult? Then don’t be that desperate guy who tries to hold onto every last inch of youth by dressing younger than he looks.

Act like a prime man — evolve your fashion, style and dressing practices. Stop wearing your cross trainers as everyday wear, your running shoes when you’re not actually running, baggy clothes that make you look foolish, and wrinkled attire that makes people think you can’t take care of yourself.

Does Your Wardrobe Need Any Changes?

Clothes closet - Men Fashion, Style

What changes are you going to make to your clothing and accessories wardrobe today?

So, there you have it — 15 key men fashion, style and dress tips to get you started on your creative journey of dressing well.

Whether you start by replacing your graphic tees with some decent polo and button-up shirts, getting nicer shoes and a color-matching belt to go along with it, or decorating your wrist with a quality watch, taking your first step into the exciting world of men’s fashion and style will make you more confident and garner more attention from everyone, including women.

Dressing well will help you become a more successful man in life.

After taking that first step, take another step, and then another to unravel the true beauty of men’s fashion and style and how it can open doors to new opportunities.

Kwame Owusu (K.O.) is an MBA and the founder of Too Manly. As a seeker of manly truths, healthy living enthusiast, and practitioner of the TooManly lifestyle, he is committed to helping men everywhere look, feel and live the prime of their life at any age.

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