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23 Habits Of A Stylish Man

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When being stylish is something you do effortlessly, it means you’ve reached a level of mastery.

No man (even if they claim it) is born stylish.

As with anything it’s something you become.

But what are the habits stylish men adhere too?

Here are the 23 habits of a stylish man, how many have you mastered?

1. They’re Confident In What They Wear

Confidence is the key element to looking good. Sure you may have just purchased a tailor made suit but how do you feel wearing it?

A stylish man never neglects comfort in return of looking good. If he doesn’t feel comfortable in his clothes it will show.

He knows who he is, how he dresses and he’s confident in whatever he wears.

confidence style

2. Everything He Wears Fits

Fit is the number 1 fundamental to good style. No piece of ill fitting clothing, no matter how much you spend on it will make you look as good as a well fitted item of clothing.

We’re not talking just suiting either.

From the denim they wear, the t-shirts, the sports jackets… everything fits to compliment their body type.

A stylish man is a perfectionist in terms of the clothing they own, making sure the trouser break falls perfectly or the shirt cuffs end precisely in the right position.

They understand the theory of how clothing should fit and everything they own follows that theory.

fit menswear

3. He Knows His Tailors Name

Talking of fit, it’s hard to buy something ‘off the rack’ which fits as it should.

Unless you’re a walking mannequin, going into your favourite store and being happy with the fit of an item of clothing is a difficult task.

A stylish man knows the importance of a tailor and typically stays loyal to one.

A tailor is the key to getting your clothing to fit, from creating bespoke pieces for you to altering clothing you’ve bought ‘off the rack’. Find a tailor who knows exactly what you want and stay loyal to them.

mens tailoring

4. He Knows Less Is More

There’s nothing beneficial about a wardrobe filled with 100’s of garments.

Less is more in the eyes of a stylish man.

Dressing well is all about investing in quality over quantity and keeping things timeless allow you to get more from less.

3 classic, well fitting Button Down Oxford Shirts in white, pale blue and navy trump 12 shirts you bought in the sale that don’t fit.

He also knows the importance of simplicity, never overdoing it with colour combinations, accessories and layering.

less is more

5. They’re Not Afraid To Spend Money On Quality

Following a timeless style they’re not afraid to invest in quality garments.

A well manufactured, well fitted £200 sports jacket is going to last longer (and save more money in the process) than a badly made sports jacket on sale for £35.

They know quality when they see it and understand the difference between Merino Wool and Cashmere.

quality clothing

6. They’re Not Obsessed With Brands

You’ll never see a stylish man head to toe in one brand, especially a brand the masses know about.

There’s no Armani logos on every polo they wear and there’s no bold slogans or branding.

Sure they may have a favourite brand they often use for ‘essentials’ but it’s typically not one the masses know about.

Just because you went to the Armani store and bought a t-shirt for more than you’d typically pay doesn’t make you a stylish man.

mens brand obsession

7. He Has A Wardrobe Built Around His Lifestyle

This heavily relates to habit 1.

A stylish man knows how he dresses and he builds a wardrobe around it.

Of course it would be great to own a number of suits and wear them daily but if that doesn’t suit your lifestyle what’s the point?

If you work in a creative position where the dress code is typically more casual than smart donning a three piece suit everyday isn’t necessary. Mastering the smart/casual look and building your wardrobe around that lifestyle would be more beneficial than buying a number of 3 piece suits because James Bond wears them.

Define your style and build your wardrobe around your lifestyle.

8. His Wardrobe Is Organised

When you look at a stylish mans wardrobe does it look cluttered?

Does anything look out of place?

A stylish man keeps his wardrobe organised, everything has a place and he utilises the habit of ‘less is more’.

From shoes neatly stored to ties and accessories being neatly put away, a stylish man has a wardrobe that is organised and would make anyone with OCD proud.


9. The Don’t Brag About How Good They Look

Ever heard someone say “how good do I look in this shirt?”

A stylish man knows his place, he’s confident in what he wears but he’ll never brag about how good he looks.

They know their style is better than others but they never verbally express it.

There’s no room for arrogance.

10. They Don’t Dish Out The Style Advice

A stylish man is very modest and doesn’t feel the need to dish out style advice to others.

Sure they’ll advise if asked but never do they freely tell people how they could look better (or as good as they do).

Cut the style advice until your asked (there’s numerous sources they can use for free) and don’t dish it out freely if you think someone needs it.

personal shopping

11. They Don’t Plan Ahead

Outfits ready the night before? Planning an outfit for a work meeting in two weeks time?

A stylish man typically won’t plan ahead.

They’re so confident in their wardrobe and their ability to put together outfits it doesn’t take them long to get ready.

A favourite video of mine is a quick video by Patrick Grant who gets ready in 30 seconds.

He’s pulled items of clothing he knows fits and he knows is suitable for the day ahead and 30 seconds later he’s ready…

The video doesn’t exist anymore (it did happen… please believe me!) But here’s a slower version showing how Patrick Grant gets dressed in the morning.

12. They Know Their Barber

Just like staying loyal to a tailor a stylish man will stay loyal to their barber.

It may take a few months (or even a few years) to experiment with Barbers at first but once they’re happy they find it hard to get a haircut elsewhere.

A stylish man doesn’t need to worry about the movies they’ve watched recently, what happened in the Football last night or any other small talk for that matter. They’re friends with their barber and stay loyal.

hair 11

13. They Look After Their Clothes

Ironing is for women? Try telling a stylish man that.

A single crease will look out of place on their dress shirt, a stain will effect the whole outfit and a scuff on their Oxfords needs taking care of.

From washing and drying correctly to the way the items are hung up a stylish man knows what’s on the care label of their clothing.

care label

14. They Pay Attention To The Finer Details

A stylish man is a perfectionist and understands the importance of the finer details.

From choosing a pocket square that compliments his outfit to the way it’s folded he knows the finer details are what makes him stand out from the rest.

The fabric, the colours, the accessories, the fit, the tie knot, the pocket square fold, the shirt sleeve roll… every finer detail counts.

pocket squares

15. Workout Clothes Stay At The Gym

Of course a stylish man needs to keep in shape but they also know that workout clothes are solely for the gym.

Don’t head to the coffee shop wearing your workout clothes to meet your friends after a heavy session at the gym.

Sure it’s ‘comfortable’ but workout clothes are solely for the gym. Tracksuit bottoms on a long flight because it’s comfortable? Don’t be lazy.


16. They Know Their Measurements

38″ Chest.

32″ Waist.

Know your measurements!

Get measured by your tailor (or do it yourself) and keep your measurements handy. Simply keep them stored in your phone or written down ready for when you shop.


17. They Get Critical At Weddings

They don’t verbally express it, that would be breaking habit 10, but they sure do think it.

“His trousers are way too long”

“How much did he pay to hire this suit?”

A wedding separates the men from the boys. From the groom to the guests a stylish man will always stand out more at a wedding.


18. They’re Not Afraid To Actually ‘Shop’

You can buy a suit at your fingertips. Literally. Grab your phone, click a few buttons and you’ve just purchased a new suit.

The issue with online shopping is being able to actually see the quality of the garment.

Relating back to habit 5, a stylish man isn’t afraid to invest money on well manufactured items. Therefore going out and physically shopping often is the best bet.


19. They Know The Rules (But Aren’t Afraid To Break Them)

Navy and black? Tie length too long?

A stylish man knows the rules to play by but they’re not afraid to break them.

Sprezzatura‘ is originally an Italian term, which would best translate as a sort of beautiful dishevelment; the art of nonchalance and perfect imperfection combining. In a style context, it is giving the impression that an outfit has been put together without a conscious effort.

9 times out of 10 a stylish man will abide by the rules but they know the correct moments to break them.


20. They Have A Grooming Routine

You could be the best dressed man in the room but if your hair is messy, your beard is un-groomed and you smell bad it’s going to have an impact on your overall appearance.

From a morning grooming ritual to an evening routine a stylish man isn’t afraid to moisturise.

alternative male grooming

21. They Clear Out Unused/Worn Clothing

Relating back to habit 8, to keep on top of an organised wardrobe a stylish man isn’t afraid to clear out unused/worn clothing.

The typical man often hoards his wardrobe with things he doesn’t really wear anymore and let’s them simply collect dust.

No stylish man will not wear something for 6 months and still have it in his possession.

Jeans battered? Shoes looking worn? If they can’t be salvaged they’re gone.

Messy Mens Wardrobe

22. They’ve Mastered The Scent

1 spray? 5 sprays? 10 sprays? How much aftershave do you apply?

A stylish man has a trademark scent that they stick too and know the importance of not overpowering the room with it.

That scent tends to be something more unique, something a little bit more classy or luxury than you’d find in the nearest Supermarket. Why? Because it makes them stand out from the rest.


23. They Know It’s Better To Be Overdressed Than Underdressed

Last but not least they always tip more towards ‘overdressed’ than ‘underdressed’.

You never know who you’re going to meet.

A future business partner, an old friend and even a future wife. Don’t be afraid to overdress and be the best dressed in the room. Just make sure you do it with confidence.

Style should be effortless.

mens style

Your Habits Moving Forward

The habits you work on shape your life so what style habits are you going to focus on?

Of course mastering all 23 may be difficult at first, but out of these habits what areas do you need to improve most on?

If you enjoyed this article don’t forget to share it and comment below if you can think of anymore.

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Paul McGregor
Paul McGregor

Founder of MFM, and short course lecturer at The London College of Fashion teaching all things marketing. Read my personal blog here.


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