How to dress well is a question that men begin to ask themselves at some point in life. The struggle with dressing sharp often comes from getting out of their comfort zone. This article will help for you to dress sharper and feel more confident without being too “out there”. 

It’s all worthwhile because being a well dressed, stylish man has its advantages in today’s modern society. Amazing things can happen when you start to care about your appearance. 

Beyond all of the things that happen to you, you start to feel like a better version of yourself. That alone is reason enough to strive for better style this year. 

HOW TO DRESS SHARP & DRESS WELL IN 2022

12 Essential Style Tips for Guys (How to Dress Well) | Men’s Fashion Advice

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Now, let’s get into 21 essential men’s style tips on how you can start dressing better today.

1. ESTABLISH A PERSONAL UNIFORM

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The truth is that we all wear a uniform of one kind or another—we use clothes to communicate our values, to create a tribal identity, to signal our power. In other words, clothes are responsible for an an incredibly complex and important task.

To make that lift easier, I’m just recommending that you front-load the work. Instead of waking up and struggling to decide the message you want to send each day, spend a little time building a wardrobe that will do the work for you. Your uniform awaits.

Two main reasons for a man to establish his own personal uniform is to avoid decision fatigue and to save time.

In fact, many powerful men have adopted a personal uniform of some sort. President Barack Obama’s primary uniform while in office was the navy suit.

As he told Vanity Fair:

“I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make.”

Obama isn’t the only one, look at Mark Zuckerberg’s sea of gray t-shirts and hoodies or the late Steve Jobs’ iconic black turtlenecks and blue jeans. Simplicity and efficiency.

Adopting a personal uniform is perhaps the best thing you can do for your style this year. [Tweet this]

Additionally, when 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.

Do you have a closetful white or blue oxford cloth button down shirts (OCBD)? Or have you amassed a mighty collection of dress shoes? Those items are good candidates to be a part of your personal uniform.

My fall/winter personal uniform these days look something like this. Functional, simple, and stylish without having to think.

Related: You might be interested in A Crash Course to Better Style.

THE BOTTOM LINE

Locking down a personal uniform imposes simplicity to not only save you time, but also frees up your mental capacity.

2. LEVEL UP YOUR LAYERING GAME

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All well dressed men know that dressing in layers is not only a smart, but stylish move. You can start with lighter, breathable and thinner layers closest to your body and thicker, heavier layers going over top.

On those chilly winter days, go with a base layer like a thermal or an undershirt. From there you can wear a button down or flannel shirt, then maybe a light down vest and finally a textured wool blazer with a stylish scarf to top it off. And if it’s frigid, you can throw on a down coat or topcoat with a pair of leather gloves.

I’ve curated a gallery of stylish men dressed in layers if you want to see some examples.

THE BOTTOM LINE

Layering up can keep you comfortably warm and looking real dapper. The great thing about layers is they can be subtracted or added as the temperature fluctuates.

3. FIND A TAILOR YOU CAN TRUST

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A habit of consistently stylish men is to develop healthy relationships with people who can help make them look and feel good. This includes, but is not limited to their barber, spiritual or career mentor, and yes, even their tailor.

Antonio Centeno of Real Men Real Style put this informative article together on finding a good tailor.

THE BOTTOM LINE

You don’t have to be all buddy-buddy, but it helps to have some sort of relationship with your tailor. The more he knows about you, your preferences and style goals, the better job he can do for you.

4. TAKE CARE OF YOUR CLOSET

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All well dressed men know the importance of taking care of their clothing—from ensuring sweaters and knits are hung on quality wooden hangers to pressing and dry cleaning garments that require it.

They also know to utilize a shoe horn to easily slide into their best brogues and shoe trees to help their oxfords retain their shape and prolong their life.

And finally, another overlooked area is jeans care and maintenance. Most guys are washing their jeans way too often. You can go for much longer than you think without washing these trusty style staples.

Related: Ensure your clothing lasts with this simple guide on Clothing Care.

Not only will your indigo and dark wash jeans be preserved, but you’ll be saving water from repeated wash cycles. The good old smell test goes a long way here.

THE BOTTOM LINE

A well kept closet may not be on your list of priorities, but take care of this often overlooked area and your style is sure to improve.

5. TAKE CARE OF YOUR APPEARANCE

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Jul 14, 2018 at 4:14pm PDT

 

 

 

 

 

 

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Aug 20, 2018 at 4:02pm PDT

Just as a clean, well cared for closet is optimal, all men can benefit from taking care of their appearance. Besides the obvious like daily exercise, eating right and regular haircuts (gotta get that fresh fade) it’s worthwhile to establish some sort of skincare routine. It becomes especially important the older you get.

My skincare routine over the past 2 years has been the Tiege Hanley level 3 skincare system which includes a daily face wash, scrub, AM/PM moisturizers, eye cream and a super serum. It’s a complete regimen with all of the essentials needed for proper skin care both day and night.

On top of establishing a skincare routine—it goes without saying—but daily showers along with proper grooming habits like keeping your fingernails and toenails trimmed go a long way in maintaining a clean image.

THE BOTTOM LINE

Your appearance plays a big part of your personal style. No outfit is going to give you a healthy glow, and so it makes sense to take care of your body from head to toe.

6. ACCESSORIZE WITH INTENTION

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Oct 20, 2018 at 4:08pm PDT

It’s easy to go wrong with accessories, for example if you wear watches that are too large for your wrist or worse, over-accessorize. I’m of the philosophy if you are unsure, to remove one accessory before leaving the house.

At the peak of my accessory obsession when I received monthly subscription boxes from Sprezzabox and Gentleman’s Box, I often wore too many pieces at a time. Looking back, it showed how unintentional I was about dressing better.

Most days you would find me wearing a patterned necktie with a tie bar, pocket square, lapel pin and an oversized watch. For me today, that’s 2-3 accessories too many. And though I don’t consider myself a watch guy, you’ll always find me wearing one when I leave the house.

Minimalist fashion watches like Daniel Wellington and Brathwait are still popular as ever. Today, I rarely wear my DW, and put on the Brathwait on occasion.

I have no issue with fashion watches like Vincero Watches, and if guys want to wear them because they like the look, go right ahead. But it doesn’t fit in with my current aesthetic which is smaller dial watches like the Seiko 5 or Hamilton Khaki Field, both excellent entry-level mechanical watches.

THE BOTTOM LINE

Accessorizing with intention shows that you are a man who isn’t afraid to show off a little personality. Just remember that there’s power in restraint.

7. KNOW YOUR MEASUREMENTS

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If I had to guess, a majority of men don’t know their measurements. I didn’t know mine, up until a handful of years ago when I became serious about how I present myself. It became especially important for me to know my measurements because I began ordering custom suits.

Since you’re reading this blog, there’s a good chance that you have ordered made-to-measure (MTM) before. And though every MTM company differs in terms of how they take your measurements, it’s good to have this base knowledge so that you can articulate how you like the fit of your shirts, pants and suits down to the exact number.

THE BOTTOM LINE

Knowledge is power. And knowing your measurements will help you nail the fit of your clothing every time you order something online.

8. CLEANSE YOUR CLOSET

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Jul 16, 2016 at 5:50pm PDT

Not this kind of cleanse, but this is important too.

At Gentleman Within, we’re all about conscious development of personal style, over a period of time. A closet cleanse can be difficult, but can also be one of the most liberating decisions you make all year.

Do you have items in your closet that you haven’t touched in years, but for some reason find impossible to toss? A shirt that’s comically tight? A pair of baggy cargo shorts that no longer represents your style?

There’s a good chance that at least a few pieces in your wardrobe are nearing their final days.

Here are a few questions you may want to ask yourself prior to your closet cleanse:

1. Does it fit?
2. When is the last time I wore it?
3. What condition is it in?
4. How does it make me feel?

Related: Take your style from good to great with a Wardrobe Purge.

If it doesn’t fit properly and isn’t worth taking to a tailor, it shouldn’t be in your wardrobe. Haven’t touched it in a year? You’ll probably never wear it again. If the fabric is torn, or in terrible shape, throw it away. And if you don’t feel great while wearing it, what’s the point?

Use your best judgement in deciding what to toss and what to keep, but I’m sure you’ll know what to do after answering the questions above. Finally, a minimalist wardrobe might be something worth considering.

THE BOTTOM LINE

Cleansing your closet can be a calming process that helps you assess what you have and what you need. Take the steps to rid of old pieces that may be holding you back and make room for new items that better represent who you are and who you seek to become in terms of style.

9. WEAR A SUIT & WEAR IT WELL

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Dec 28, 2017 at 3:26pm PST

Many men feel that suits are stuffy, uncomfortable and inappropriate for most situations. All valid points. But let me tell ya—wearing a suit well is a hallmark of a well dressed man.

It’s like a layer of armor that’ll make you feel ready to ride into battle and conquer the world. Okay, I may be exaggerating a bit, but wearing a suit really is more than just a style enhancer.

Why it’s worth it to suit up:

• People treat you better
• You stand taller
• Women want to date you
• You smile more
• Men want to be like you
• You feel more confident
• You will actually be a more stylish man

If you still feel that wearing a suit will put you out-of-place, check out this Dappered post on places to wear a suit where you normally wouldn’t.

And for a comprehensive guide on buying an off-the-rack suit, check out our recent guest post over at The Dark Knot.

THE BOTTOM LINE

There’s a reason they say to “dress for the job that you want, not the job that you have.” Wearing a well-fitting suit projects an image that can set you up to succeed in business and in life.

10. INVEST IN QUALITY SHOES

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Good style starts from the bottom up and the shoes that you choose to wear can say a lot about you. They’re a big part of your overall appearance. Just ask the ladies.

So maybe you feel that you’re not fashion forward enough to wear a pair of tan brogues. Or maybe $300+ shoes seems outrageous to you. For the longest time I thought the same, but not anymore.

Related: Level up your shoe game with these Essential Shoes For Men.

When it comes to dress shoes, it pays to invest in quality that will last for years and even decades to come. And similar to wearing a well-fitting suit, a clean pair of oxfords will attract the right kind of attention.

My suggestion is a pair of brown cap-toe oxfords like the Allen Edmonds Park Avenue in a dark brown or oxblood color. And if you’re feeling more adventurous, the AE Strand in walnut or navy.

THE BOTTOM LINE

Shoes speak volumes about a gentleman. This is one area that you do not want to skimp. Buy the best quality you can afford.

Quick note: If you’re enjoying this article on how to dress sharp & dress smart, then you’ll probably find my other writing on all things men’s fashion & style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.

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11. CURATE YOUR ESSENTIALS

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Jan 7, 2018 at 11:17am PST

Of course your essentials may be different from mine. But there are several essentials that I feel all men can benefit from having in this closet, especially when building out his wardrobe early on.

Here are some of my key menswear essentials:

First things first is a great fitting, plain white t-shirt. Once you’ve acquired that, move on to other versatile colors like gray and navy. My current favorite t-shirt brand is UNIQLO and their line of Supima cotton tees for under $20.

Secondly, go get yourself a few crisp pairs of white and light blue oxford cloth button down shirts (OCBD). These are two of the most versatile color OCBDs in my opinion. These shirts are the perfect piece to create a smart casual look that will have you looking great at work all the way to happy hour. And they look fantastic paired with my next essential, dark blue jeans.

Next, pick up a few pairs of slim, straight or relaxed dark wash jeans depending on how you like yours to fit. My preference is always slim. No need to break the bank on designer brands, but it’s a good idea to go for quality here as these jeans should last you for years to come.

A few of my favorites are Levi’s 511 (slim) with stretch, Levi’s 512 (slim taper) with stretch, and Banana Republic’s Traveler Jean, and American Eagle‘s AirFlex Slim Jean.

Finally if you’re looking to graduate your style, look no further than the iconic navy blazer. To me, it’s a style staple that separates the men from the boys.

THE BOTTOM LINE

Your essentials will be at the core of your wardrobe and so it’s important to intentionally curate them. Whether you’re on the lookout for various jacket styles or shirt styles, take some time to figure out what your essential styles are and go pick them up.

12. PLAY WITH PATTERN, COLOR AND TEXTURE

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Master class in layers, texture, color and pattern courtesy of @gui_bo. Go read his menswear 10 commandments? (Link in his bio) #Details

A photo posted by Gentleman Within (@thegentwithin) on Nov 21, 2016 at 5:37pm PST

A little bit of color never hurt anyone. Colors tell a story. Textures can too. As can patterns. What we wear, ultimately tells a story. If what you normally wear is more on the reserved, neutral side, then spice up your life with some pattern, color, and texture (PCT).

 

 

 

 

 

 

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Jan 22, 2018 at 4:27pm PST

Here’s an analogy for why PCT works:

As a “graphic designer” I’m used to hearing the term, “make it pop” which is code for your design looks a little flat. Usually the solution is simple. Simply inject some color, perhaps throw in a few textures and patterns and voila, I’ve got a design that sings.

This works the same way with style. Just start adding PCT into your outfits. Don’t be afraid to play. Kids aren’t afraid of failure and rejection. Be like a kid. Fail, learn, and keep playing.

THE BOTTOM LINE

Adding a dash of pattern, color and texture into your outfits can liven up style gone stale. Don’t be afraid to experiment and learn as you go.

13. GET OUT OF YOUR STYLE COMFORT ZONE

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In life, we feel most alive when we intentionally get outside of our comfort zones. Many people are content living in a safe bubble, but what happens when it bursts as all bubbles do? You’ve got no choice but to try something new. This, ultimately is how we grow.

Just like personal growth in life, you’ll begin to dress well by putting in concerted effort. But you have to be willing to experiment and try new things.

Whether there’s a new sneaker trend you’ve been wanting to try out or have been leaning heavily towards monochromatic / tonal dressing, there’s always room to play with your personal style.

THE BOTTOM LINE

Go find inspiration and learn how to make a statement as you begin to level up your style.

14. REMEMBER YOUR SUNGLASSES

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Sep 18, 2018 at 12:54pm PDT

Wearing sunglasses helps with facial symmetry, and symmetric things appeal to human eyes. Dark lens sunglasses also provide an air of mystery to the wearer. If you can’t see a person’s eyes, you have no idea what they’re thinking. It’s no wonder why sunglasses can make you look so cool.

The classic RayBan Wayfarer, one of the most popular sunglasses styles over the past decade is a nice pick since most people look good in them. Right now I’m loving the Christopher Cloos brand and Felix Gray.

I’ve also tried Warby Parker and offer quality and stylish glasses for men and women, mostly under $100. Their home try-on program is super helpful. They allow you to select 5 frames to test out for 5 days and they’ll ship for free.

THE BOTTOM LINE

A quick way to instantly appear more stylish and well dressed is to throw on a pair of flattering sunglasses. You’ll look cool, not to mention help prevent wrinkles forming around the eyes from squinting so much on sunny days.

15. TRY A SUBSCRIPTION SERVICE

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Apr 12, 2017 at 5:45pm PDT

You may have seen online ads for Stitch Fix, Menlo Club, Trendy Butler, Bombfell or Trunk Club at some point. It seems a new men’s clothing, subscription service pops up every year.

Men like automation and making life easier, and that’s exactly what a subscription service can help you with. Many are pay as you go, so there’s no long-term commitment for you, unless you pay for the year upfront, usually at a discount.

If you want to check out some cool boxes, Kyle Ingham over at The Distilled Man put together this comprehensive roundup of 50 awesome subscription boxes for men.

THE BOTTOM LINE

Today, there’s a subscription box for men of all kinds. There’s boxes to help you dress better, eat and drink better, date better, and level up your life so that you can live better.

16. FOCUS ON THE FIT OF YOUR CLOTHING

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Mar 22, 2018 at 6:57pm PDT

I feel like a broken record talking about fit, but it’s worth stressing that wearing clothing that fits your body is of utmost importance. It has the power to make or break your style in an instant.

Related: You might like this article on why Fit is King.

A man wearing a $3,000 Prada suit, that’s ill-fitting could look homeless. In the same way, a man wearing a $100 H&M suit can look like million bucks after a few minor alterations.

With so many different things for a man to consider when dressing for his body type, it’s easy to see why so many men struggle with fit. Take some time to check out this aptly named site on how clothes should fit.

THE BOTTOM LINE

Wearing clothes that fits your body is the most important rule in menswear and one that you don’t want to break. Understand this concept and half the battle is already won.

17. PREPARE YOUR OUTFIT THE NIGHT BEFORE

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Oct 18, 2018 at 12:21pm PDT

Mise en place is a French culinary phrase which means “putting in place” or “everything in its place.” It refers to the set up required before cooking, and is often used in professional kitchens to refer to organizing and arranging the ingredients that a cook will require for the menu items that are expected to be prepared during a shift.

Why not apply this concept to getting dressed?

I’d say the majority of people don’t think about what they’re going to wear in advance, unless there’s a special occasion or important meeting coming up.

If you’ve ever found yourself frantically grabbing random pieces out of the closet as you scramble to get out the door in the morning, then maybe you could try a little “mise en place”.

Whether you’re into suiting or casual dress, a little preparation will set you up for a smooth transition from the bed to the bathroom and beyond.

THE BOTTOM LINE

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 — you’ll elevate your style and be able to curate a dope fit without even thinking.

18. STEP UP YOUR CASUAL WEAR

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Mar 9, 2018 at 3:45pm PST

Casual style is one of the most popular clothing styles for men. Things get complicated because “casual wear” means different things to different people.

For example, Jimmy’s definition of casual wear is sweatpants, t-shirt and sneakers while Jason’s definition is dark denim, OCBD and brown brogues. Neither of them is wrong.

 

 

 

 

 

 

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Jan 16, 2018 at 9:27am PST

I like to think of casual wear as comfort first and style a close second. There are also levels to casual wear. Smart casual is a more elevated and refined type of casual style like Jason’s definition. Whereas Jimmy’s definition is more of a dressed down athleisure aesthetic.

Whatever your definition is, the key to nailing it with men’s casual style is to master fit, drape and silhouette. It’s not the first time I’ve talked about this, but if you can hone in on and master these things, your casual style will be on point.

THE BOTTOM LINE

Casual wear will always be in style for men. Whether you like a more dressy or dressed down men’s casual fashion, focus on fit, drape and silhouette to step things up.

19. GET BACK TO BASICS

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It’s easy to forget the basics, which is funny because we wear them the most. No matter how far along you are on your style journey, there’s always room to invest in quality basics. Things like solid t-shirts, undershirts, boxer briefs or boxers, lightweight joggers, nice dress socks, and even no-show socks.

THE BOTTOM LINE

The basics are easily overlooked, but it’s a good idea to refresh our wardrobe basics every so often as these are articles of clothing that get the most wear.

20. MASTER THE LITTLE DETAILS

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A post shared by Khoi N. | Style for Men (@thegentwithin) on Sep 14, 2017 at 4:14pm PDT

How often do you pay attention to things like the roll of your pants or allowing a sliver of sleeve cuff show under your suit? Are you conscious of the appropriate time to wear fabrics like corduroy or chambray? Can you effortlessly mix and match patterns, colors and texture? How about pairing pocket squares and ties?

A meticulous attention to detail separates a stylish man from the rest. [Tweet this]

Stylish men are all about noticing the little things. They pay attention to how their jeans are cuffed. It’s intentional when the shade of their belt matches the shade of their shoes.

A master of details is someone who puts a price on personal presentation. He puts his best foot forward and dresses like he cares. He leaves the house not only stylish, but the best version of himself.

For some details inspiration, take a look at this gallery I’ve curated on Pinterest.

THE BOTTOM LINE

Great style is in the detail. Start paying attention to what you wear, how and, why you wear it. It makes a world of difference.

21. Be aware of rules and trends, but in the end DO YOU!

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There are rules in menswear, but as the adage goes, “rules are meant to be broken.” And fashion trends are ever fading. You don’t always have to fit in. Break the mold and create any image you want.

You can be the guy who wears suits just because. Who cares what people think.

Ultimately great style is about confidence, owning it with whatever you decide to wear. [Tweet this]

Of course it has to be in line with your personal style and who you are.

THE BOTTOM LINE

Being aware of style rules and fashion trends is cool, but it’s important to wear what flatters your body type, makes you feel great and ultimately makes you, you. Do this and I guarantee you’ll be a well dressed man.

WRAPPING THINGS UP

Congrats on making it all the way through over 5,000 words on how to dress sharp & dress well as a man. Sometimes all it takes is getting out of your comfort zone. If you follow this guide, you’ll certainly stand out, but in a good way.

Although some of these require little effort, others demand more patience and thoughtfulness. Naturally, humans suck at trying to do too many things simultaneously. And so, to avoid overwhelm, I suggest starting with one or two of these fashion tips at a time.

Be patient, Rome wasn’t built in a day and neither is personal style. [Tweet this]

Cheers to your style!

WHICH OF THESE TIPS DO YOU PLAN TO IMPLEMENT THIS YEAR?

To continue the discussion, come and join the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.

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