7 Habits of Highly Stylish Men

Over 25 years ago Stephen Covey published his bestselling book, 7 Habits of Highly Effective People. The headlines, in case you haven’t come across it, are as follows:

  1. Be Proactive
  2. Begin with the End in Mind
  3. Put First Things First
  4. Think Win/Win
  5. Seek First to Understand and then to be Understood
  6. Synergize
  7. Sharpen the Saw

If you want to unpack some of those headlines further the book is well worth a read.

But it set me thinking about the equivalent 7 habits of highly stylish men. You know the ones I mean; whenever you see them, and I mean whenever, they somehow manage to look effortlessly and unselfconsciously stylish.  What’s the secret?tumblr_ldk3mpxLCB1qc9njco1_500

1. Plan ahead

Highly stylish men plan ahead, determining the night before, perhaps the weekend before, what they will wear.  If it is not a combination they’ve worn before they’ll try it on so that they know it works before they wear it. They may get opinions from a trusted friend or family member about which combinations work and which ones should be left well alone.

If you roll out of bed and get dressed in the 10 minutes between getting out of the shower and leaving the house, you’ll be glad that you figured what to wear the night before.

Gandy Telegraph
Image: David Gandy in The Telegraph

2. Learn from the best

No one is born stylish; we all have to learn.  Those who are highly stylish learn from the best. Look at what stylish people are doing and learn from them.  Pay attention to how outfitters dress their shop windows and emulate those combinations that appeal to you.

suit-tailoring Telegraph
Image: The Telegraph

3. Pay attention to fit

Stylish people know that well fitted clothes are always stylish.  So they  pay attention to having their clothes adjusted where necessary so it fits them just so. They realise how you wear an item of clothing is a reflection of how well it fits. So you wear something with greater confidence if you like the way it drapes over the particular contours of your body. Highly stylish men will often not be wearing the most expensive clothes in the room. But theirs will be among the best fitting.Wardrobe

4. Prefer quality to quantity

Having paid attention to fit, highly stylish people pay attention to quality, in that order.  Once they have a core set of staples in the wardrobe they prefer to buy one or two quality items per year which are always going to be stylish rather than a large number of  poor quality items, especially if they are faddish and will no longer be ‘on trend’ in a few months time. However, they recognise that quality does not always have to be expensive.

Image: Gaziano Girling Sinatra Black

5. Spend more on shoes

The highly stylish  recognise that spending more on shoes pays dividends in the style stakes. Great clothing with poor shoes?  You look like a pretender. Slightly shabby clothing with great shoes? You look like a stylish man dressing down. The holy grail, of course, is great clothing topped off by great shoes.  If you can manage it, your should should be high quality leather but not overly showy.  The best shoes are not only well constructed, they have beautiful timeless silhouettes.

ExpertTips-Tailoring6. Have a default setting

Highly stylish men have a default setting. They have worked out what works for them and they will repeat this look with slight variations. This might be a colour scheme; for example, some people simply look great in various shades of grey. Alternatively, it might be a certain look. The man who looks good in a three-piece-suit may have a default setting that is some combination of jacket, waistcoat and trousers.

It is interesting how many images there are of David Gandy wearing a three piece suit. Found a pair of trousers that works? They buy them in multiple colours.  Because they are playing with variations on a theme, which is their default setting, they always look good.anand-carlsen-game7-world-chess-2014

7. Play the long game

Highly stylish men are not in a hurry. Instead they build up a wardrobe of depth and quality over time, and similarly build up their own experience and self awareness, so that whatever life throws at them they can usually put together something stylishly suitable for that occasion.

And if they don’t get it quite right on this occasion, they know that it’s only clothes after all. No harm no foul. They’ll try something else next time.




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