20 Habits Of Stylish Men | Classic Style Routines

20 Habits Of Stylish Men | Classic Style Routines
No man is born stylish.
It takes effort to acquire a studied perfection in the art of dressing well.
There is an old proverb which says that habit is second nature. 
Effortless style is a habit for some men.
Their fashion choices are guided by certain principles that over time become second nature.
These habits are not difficult to learn. In fact, any man who applies these principles will improve his style to an extent where he doesn’t even have to think about it.
Great style becomes a subconscious part of your daily routine.

Style Habit #1 Feel Comfortable In Your Clothing

 20 Habits Of Stylish Men | Classic Style Routines

There are two parts to the equation of comfort in regards to clothing.

Part 1 – Be confident in what you wear. 

Stylish men practice being the best-dressed man in the room. Over time, the confidence gained from this simple practice allows them to feel comfortable in smart attire. This is true as much in style as in any other art form – practice builds comfort.

A smart man understands that his appearance is a reflection of his core values, his family, his business and his lifestyle. Dress in a manner that suits these factors.

Part 2 – Everything you wear fits.

Stylish men are not penny wise and pound foolish. They never try to save a quick buck that will cost them a lot more in the long run. Even if an item of clothing is marked at a 90% discount, they wouldn’t bother buying it if it doesn’t fit.

The real value of clothes is reflected in how often you wear them. Well-fitted clothes look stylish and feel comfortable. Consequently, they become the most-worn items in your wardrobe.

Style Habit #2 Dress For Your Body, Events, Weather, & Yourself

Stylish men are never ruled by vanity.

 20 Habits Of Stylish Men | Classic Style Routines

They don’t allow their better sense of judgment to be overruled by fashion trends that are the current rage.

They are sensible in their choices because they understand what suits their body type, the events the attend, the weather and their lifestyle.

Their choices are not dictated by what looks good on someone else. Instead, they base their choices on:

  • The weather: Dress appropriately for the climate in your location.
  • Natural features: Is your frame small or large? Wear clothing that compliments your build and not clothing that either makes you look like a giant or a dwarf.
  • Appropriateness: Dress appropriately for the event or occasion you are attending.

Style Habit #3 Know Your Tailor’s Name

It takes a skilled tailor to create a stylish attire that fits right on your body. A stylish man understands the importance of a skilled tailor and makes the effort to build a friendship with one he trusts.

 20 Habits Of Stylish Men | Classic Style Routines

Get your clothing adjusted – even new clothes. from suits to casual clothing to jeans. Except for t-shirts and athletic shorts, you should have the rest of your wardrobe altered to fit your body.

Style Habit #4 Know Your Barber (or Hair Stylist)

Know your hair stylist or your barber. Set up a time every month to have a hair cut. Pre-pay if you can, so you are forced to show up for your appointment.

 20 Habits Of Stylish Men | Classic Style Routines

Don’t be reactionary. Don’t wait until you suddenly realize one morning you need a haircut but it’s too late because you have an interview that same morning. You may end up with a bad cut, spend more at an expensive salon or end up with a barber who doesn’t understand what hair style suits you.

Style Habit #5  Clothing Maintenance

Washing, repairing, pressing, shining shoes. 

 20 Habits Of Stylish Men | Classic Style Routines

A stylish man knows how to wash his own clothes. Especially delicate items like sweaters.

Use a batch-processing system that saves time and energy. I wash all my shirts together once a week and let them dry naturally before pressing them all at  once. This system saves me time and ensures that all my shirts are ready to wear at one go.

Broken buttons? You don’t want to find out when you’re running late for work. Scruffy and dirty shoes? Early mornings are probably the worst time to take care of these details. I shine all my shoes once a week.

If you have the money, send it out to the cleaners.

Style Habit #6 Everything Has A Place

Great style is not restricted to the clothes you wear.

 20 Habits Of Stylish Men | Classic Style Routines

It starts with simple decisions like having a dedicated place to store your clothes, your shoes, and other accessories.

Have a dedicated place where everything is stored so you find it when you need it.

A shoe shine box makes it easy to shine your shoes. Having a dedicated space to accomplish simple tasks makes them easier to complete in the shortest amount of time.

Style Habit #7 Justifying Cost Of Clothes

Buying good quality clothes is better than buying something on discount for the moment.

 20 Habits Of Stylish Men | Classic Style Routines

Stylish men ask themselves a straight-forward question – is this article of clothing timeless?

Is it going to be stylish 5 years from now? If an item costs over $500, this question should be the deciding factor in your purchasing decision.

Remember, the value of clothing is represented by the number of wears weighed against the cost. 

Style Habit #8 Function and Comfort Are More Important Than Style

Function and comfort should never be sacrificed for style. That takes you into the realm of fashion purely for aesthetic purposes.

20 Habits Of Stylish Men | Classic Style Routines

Use clothes as a cover (function) and make sure it feels good (comfort) while paying attention to the third part of the equation – the importance of aesthetics in modern society. Your style and appearance does affect basic human interactions.

There’s a big difference between getting dressed in style and just covering yourself.

Style Habit #9 Pre-Set The Details

Pre-setting the details takes the thinking out of the process. details

20 Habits Of Stylish Men | Classic Style Routines

Where do I store the pocket squares? In the pockets of my jackets. My other pockets already hold a spare set of business cards, saving me precious time when I am rushing out to a conference.

Plan your outfit the night before. Store your watch, pocket square, and other accessories together with the outfit. Pre-setting some of these details will ensure that all you have to do is throw on your jacket before heading out the door.

Style Habit #10 Compliment Freely But Avoid Dispensing Style Advice

Dispense style advice only when you are asked.

20 Habits Of Stylish Men | Classic Style Routines

I was with a friend recently in a public place. While we were interacting, a stranger reached across and straightened my friend’s tie-bar, completely unaware that my friend had intentionally worn his tie-bar slightly crooked (the Italians have a word for it –sprezzatura).

Don’t be the annoying guy who pushes his ideas on someone else without them asking for your opinion.

Instead, when you notice someone who is attractive or gone the extra mile in terms of style – verbalize your appreciation.


The 10 habits listed above are a starting point. Great style is a combination of many more heuristics that are designed to save time, finances and embarrassing moments.


Bonus 10 Timeless Habits Of Stylish Men

Need some more rules-of-thumb to ensure you are always at your best?

Style Habit #11 – Own A Well-Fitted Dark Suit

20 Habits Of Stylish Men | Classic Style Routines

You need to own at least one complete well fitting dark suit. Have it ready in case you are invited to a wedding, an interaction with the president, need to attend a funeral or give a presentation at work.

Style Habit #12 – Treat Color Like A Spice

20 Habits Of Stylish Men | Classic Style Routines

Color is the secret ingredient that can spice up your wardrobe.

A selective use of color complement or spruce up an otherwise plain outfit. A red tie can turn a straightforward charcoal business suit into a power outfit.

A pair of brightly colored socks can lift the spirit of a solid-colored ensemble.

Style Habit #13 – Workout Clothes Are For Working Out Only

20 Habits Of Stylish Men | Classic Style Routines

You may have just walked out of a sweaty gym session and need to rush straight to drinks with friends.

That is not an excuse to show up in your athletic gear.

Avoid using the excuse of comfort – your track pants may be comfortable to wear at home, but wearing them at the airport for an international flight shows a lazy attitude.

Style Habit #14 – Understand The Power Of Scent

20 Habits Of Stylish Men | Classic Style Routines

The number one criteria for women in mate-selection is scent. That’s the power of those invisible molecules wafting from your body.

Pay attention to your body scent – select a suitable fragrance, shower daily and avoid foods that affect your body’s natural odor in a negative way.

Style Habit #15 – Know Your Measurements

20 Habits Of Stylish Men | Classic Style Routines

And keep them handy. Store them on your phone or in a file that is easily accessible when you are out shopping.

Never buy clothing that doesn’t fit you properly – knowing your measurements you ensure you don’t rely on the manufactures sizing charts.  Instead always buy the right size for YOU (per your measurements)!

Style Habit #16 – Building A Core Wardrobe That Suits Your Lifestyle

20 Habits Of Stylish Men | Classic Style Routines

Own a core wardrobe that works for your lifestyle. Purchase selective items that are interchangeable.

With just 21 core items, you can have a fully functional wardrobe that will be appropriate for most occasions in modern society.

Style Habit #17 – Buy Duplicates Of Your Favorite Interchangeable Items

20 Habits Of Stylish Men | Classic Style Routines

If you wear an item more than three times in a week – buy another of the same item immediately.

It could be underwear from a certain brand, a t-shirt with the right fit or jeans in the perfect cut. If you are bound to wear a certain item of clothing for more than three times  week, have a ready substitute of the same item.

Style Habit #18 – Know The Rules & When To Break Them

20 Habits Of Stylish Men | Classic Style Routines

A stylish man knows the rules but is confident enough to break them. You first have to know the rules before you can break them.

The Italians have a word, sprezzatura, which describes a certain nonchalance in how a man dresses. To achieve the ‘deliberately-disheveled’ look of nonchalance, a gentleman first needs to understand the inner workings of style.

Style Habit #19 – A Weekly Grooming Routine

20 Habits Of Stylish Men | Classic Style Routines

Good systems are an essential part of a stylish man’s routine.

Have a set time each week to cut your nails, trim your beard and check your nose and eyebrow hair.

Allocating time for these activities takes the pain out of sudden surprises and embarrassments from lack of care.

Bonus Style Habit #20 – Let Go Of Worn-Out Favorites

20 Habits Of Stylish Men | Classic Style Routines

Use a simple formula. For each new clothing purchase you make – donate an older item of clothing from your wardrobe.

This way, your wardrobe stays clean and minimal, ensuring that your clothing choices are easy, fast and stylish.

No one wants to see you in public wearing your worn-out and tattered t-shirts from college.


Our habits shape our lives.

Any person who is not conscious about making healthy choices a part of their life is going to end up with some undesirable habits.

Poor taste in fashion and style is a result of not making the effort to learn these simple habits to improve your style.


Read More:

9 Must Haves in Men's Closet | Men Style Digest


Antonio Centeno
Brad Jones

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