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14 Signs of A Stylish and Sophisticated Man

Style is more than owning expensive clothing and it’s not enough just to look good.

True style and sophistication comes with an understanding of numerous aspects of grooming, dress, and attitude.

Put all three of these together with an honest personal assessment and you get a picture of a far more interesting gentleman than your average blasé Joe.

A man who neglects one or more of these areas of concern can stick out as immature, uncaring, or worse.

different types of dress shoes for men

1. Proper Shoes For The Occasion

Being stylish involves much more than simply having style.

A man who truly knows what he’s doing will also know when exactly certain pieces from his wardrobe are more appropriate for the occasion than others.

Fewer pieces are more important in this area than the pair of shoes. It may be cliché but you really can tell a lot about a man from his choice of footwear.

Chukka Boots, for example, are perfect for most business casual situations as well as important social ones like a first date. In fact Chukkas are a smart casual choice as they are sharp enough for the office In khakis or jeans and show a little extra class during happy hour.

Loafers, on the other hand, may be too formal for most first dates other than elegant dinners or late-night outings. Clean, well-maintained sneakers are better suited for lunch dates or walks through the park but the emphasis is on clean and well cared-for.

A man who decides to wear the same sneakers on a date with which he takes Fido out on a walk better get used to spending a lot of time alone with man’s best friend.

hair clay vs other mens hair care products

2. Embracing A Hairstyle That’s Your Age

Men, women–we’ve all been there: The dreaded high school hairstyle.

Not that there was truly anything wrong with your hairdo back in school but, as with most things from that era, moving on is encouraged.

A sophisticated man maintains a hairstyle more suitable for his age which for most all men no longer in their 20’s also means well-trimmed and cut.

Again, there’s nothing wrong per se with a man having hair down to his shoulders if he’s young and still figuring himself out or if he’s some kind of artist or musician.

Older men however should heed the words of their mothers in their youths and go get a gosh-darn haircut.

For a comparison on the top hair products for men, check out this in-depth guide.

tailored dress shirt

3. Knows His Tailor By His (or Her) First Name

There’s probably no surer sign of a sophisticated, stylish man than him being on a first-name basis with his tailor.

Just try to say the words “tailored suit” without feeling even a little fancy. Having clothes fitted to personal, exact specifications is the ultimate expression (for men) of careful consideration for one’s looks.

To a lesser but still notable degree, men who make sure to wear clothing that fit them well without the need of a tailor also have a greater sense of style.

Those who wear a particular article of clothing just because it fits fail to consider whether this fit is the best for their body shape and type.

4. Knows How To Match His Clothes

You may think knowing how to match various elements of an outfit is a no-brainer but If it were there’d be more GQ’s and fewer People of Walmart. But it doesn’t have to be as complicated as remembering not to wear a camouflage tie with a gingham shirt.

One of the surprising secrets to matching a tie with a shirt, for example, with the same pattern is to be sure they are different sizes.

Take a striped tie for instance. Clever men know that their shirts’ stripes ought to be either larger or smaller than their ties’ but never the same size.

The match shouldn’t be that perfect. All that does is strain people’s eyes and makes it look like you’re wearing a costume. As far as color, classic sophistication is well-captured by looks that pull together multiple shades of the same color.

For an edgier sense of style though, men can play around with complementary colors like red and green, yellow and purple, and blue and orange.

maintaining a beard

5. How To Maintain A Beard

Fortunately, it’s quite easy to tell whether a man takes care of his beard. All you’ve got to do is look him in the face.

Trimming is essential for all beards even for men who don’t shave regularly.

Facial hair kept neat and tidy is also a good sign that a man has a solid personal care routine.

This is not to suggest that baby-smooth skin or sexy stubble are the only ways to go.

Sophisticated men with large beards or long mustaches will have invested in a good pair of trimming scissors and a quality beard comb.

All men, but especially those with a lot of facial hair, should wash and condition their beards regularly through either a beard oil or beard balm. You’ll likely be able to tell who does and who doesn’t both by the fullness and luster of their beard.

best cheap cologne for men

6. Wears The Right Cologne For The Occasion

A man who considers himself refined takes a couple of factors into account before selecting his cologne for an occasion.

Is it daytime or nighttime?

Is he going out in the summer heat or venturing through the winter cold?

For evening outings, men should wear something spicy like sandalwood or a warm musk. In the daytime, suave men want to wear a fresh, light cologne.

Fragrances with notes of heavier scents like leather have the greatest impact during the winter months.

Tropical or airy colognes should be kept waiting to be carried off in the summer breeze.

Review of the best solid colognes and cheap colognes.


7. Isn’t Wearing Eyewear That Is Two Generations Old

If you’re still wearing the same eyeglasses that you wore in high school, there’s something wrong with you.

No really, like, you should probably re-check your prescription as your vision’s likely gotten worse over the years.

Eye health aside though, a style-check should be in order at least every year or so. We all can sometimes collectively fall into fleeting fads; think cat eye glasses or perfectly round shades.

Nowadays, companies like Warby Parker make it easy to keep up with changing trends. They graciously send you any five frames of your choosing for free, you choose whichever ones you like, and send them back for free.

Warby Parker even takes their commitment to style a step further by offering the input of personal stylists via phone, email, or social media.

8. Owns Their Look – No Second Guesses

Nothing screams sexy and sophisticated more than confidence in a man.

That’s just the way it is.

As humans, we are all naturally drawn to people who are confident and secure with themselves. Being comfortable in your own skin should also extend to your style.

A man who owns his look or, in other words, knows he looks good without being cavalier, will always appear sophisticated.

What’s more, if a man were to follow all of the advice here but fail to own his look, he would be doomed to failure no matter how good he looks.

thrift store finds

9. Visit The Thrift Store And Find Vintage or Timeless Pieces

We’re not talking wearing your granddad’s clothes like Macklemore, unless your granddad had a great sense of style himself.

Passing over the fugly sweaters and such, a seasoned man knows how to spot the real gems.

Quality leather oxfords, mens merino wool sweaters, natural fiber suit jackets, and timeless ties are all out there waiting to be uncovered.

A man who is both stylish and smart recognizes the true value and potential of vintage clothing.

best undershirt for men

10. Knows How To Wear An Undershirt

A lot of men put very little thought into their choice into quality undershirts.

After all, they tend to be covered up by something seemingly more important, namely a dress shirt. Although if a man is wearing a basic white tee under a lightly color dress shirt, it is in fact going to be visible through the fabric.

Undershirts are fine and even necessary but we don’t want to see them; hence the name. To keep his look classy a stylish man opts for a heather gray undershirt which blends invisibly underneath most dress shirts.

Heather grey shirts also have the added benefit of obfuscating sweat stains. Men also want to be mindful of the types of collars on their undershirts. Hanes’ recent introduction of the lay flat collar, in a commercial starring the undeniably debonair Michael Jordan of course, helped bring a fashion emergency to light.

Bacon neck, not as delicious as it may sound, is the wavy warping of an undershirt collar reminiscent of a tasty piece of cooked bacon.

This tends to look bad under a dress shirt, causing it to take on the same wrinkles and looks even worse with the top button undone.

right bag for the occassion

11. Wears The Right Bag For The Task At Hand

School’s out, so men should set aside their backpacks and get familiar with the different types of bags.

Most men are familiar with briefcases as they are a classic workplace mainstay. For many industries, messenger or carrier bags have gained a leg up on that mainstay status as more people lug their laptops to work.

Holdalls or carryalls are perfect for travel.

They have plenty of space including multiple pockets and are made to fit airline carry-on specifications.

Dopp kits for the toiletries, garment bags for the suits, men have far more fashionable options in bags than the humble but not-so sophisticated book bag.

suits for men

12. Owns More Than One Suit

Men who are way ahead of the game will already own more than one suit.

People can easily pick up on when someone is frequently wearing the same t-shirt or sneakers, so you can be sure lacking a change of suits won’t go unnoticed forever. Keep wearing the same old suit over and over again and eventually snide comments and sneers will abound.

Remember the thrift store is always an option, so there’s no real excuse for a man not to have more than one suit. At the very least, he ought to have options between all the elements necessary to mix and match various formal and business casual looks.

Having a couple of different suit jackets will go a long way for a time but a sophisticated man will want to fully invest in himself at some point with several different suit options.

dressing your age

13. Dresses Their Age

Just going to come right out with it: Graphic tees are a poor style choice for any man over the age of 35.

And if he’s in his 40’s, you might as well stick a fork in him ‘cause he’s done. It’s all over at that point. That is, unless he is robbed of the delusion that he’s the same dude he was back in his 20’s.

For a little reverse shell-shocking back to reality, men should try…well, a makeover. Change up their style based on the tips laid out here and see what, if anything, changes about their day-to-day life.

Naturally, more attention, paid compliments, and longer looks are all good indicators of success. It would just go to show that there is little reason a man would not want to dress his age in the first place.

cleansing men skin care

14. Skin Care Routine Is On Point

Men can be notorious for a lack of skincare knowledge.

Sure it may be true in general that men tend to age more gracefully than women, but at the end of the day, we still all have the same skin.

Skin that needs to be cared for.

A smooth gentleman needs smooth skin which comes only either from youth or quality face creams. Middle-aged men should begin considering anti-aging skin care products or, at the very least, preventative care products.

Taking care of your skin is a like a gift anyone can give themselves and one that continues to pay off more and more as time goes by.

Plus, there’s no better complement to a keen sense of style and strong self-confidence than a handsome face.

About Adam

As the lead editor of Tools of Men, Adam is an expert in all things men's grooming and style. When you don't find him reading up on the latest style trends, he likes to go jogging, attempt to distinguish the differences between IPAs, and play sports with his kids.

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