The Personal Image System Podcast

21: Habits of Stylish Men

April 25, 2016

Show Notes:

Habit is one of the most powerful tools that humans have at their disposal. When it comes to effecting real change, and accomplishing large goals, there is nothing as powerful or effective as steady progress toward those goals, and that is what a habit can accomplish. Habits have the almost magical power of breaking up very long-term processes into steps, and giving you consistency in reaching them. This is the secret of really stylish men: They have made good fashion a habit.

Small activities that are accomplished every day without fail give you not only consistent progress toward accomplishing your goals but, in essence, they fool-proof your style to help you dress well every single day even if other things go wrong. For example, if you make the habit, every single day, of laying out your outfit for the following day the night before, then when you accidentally sleep in, your outfit will not suffer, because it’s actually easier to put on the clothes you careful choose and laid out the night before.

This is just one of many examples of the ways in which habits are a powerful tool to help you dress better and come across as more accomplished and confident. Listen to this episode to get the rest of the habits you should be making a part of your everyday, such as shoe care and clothing repair. Learn how to leverage habits to be your best self through good style on this episode of The Personal Image System!


Key Takeaways:

  • There’s no one big change that will make you better able to leverage the power of style. It’s small changes, consistently over time. It’s habits
  • When you employ habits to help you be more stylish, you are using one of the most powerful tools humans have
  • Small changes, things that you do daily, are what is going to help you really become a better dressed and more stylish man
  • One of the key habits is taking care of your shoes. Clean, condition, and polish your shoes. Get a simple shoe shine box. Just having the box, and everything you need to clean and shine your shoes in one place, will make you far more likely to do it
  • Clean your shoes daily, and condition them weekly.
  • Polishing will help prevent salt and other things get on and in your shoes. It protects the material
  • When you have good footwear, and you take care of it, it only looks better with time
  • Make a habit of taking care of your clothing. For instance, if you see a button about to fall off, don’t put it off until later. Fix it right then
  • Brush your suit after you wear it
  • Lay out your clothing the night before

  • Consider using a subscription service
  • Schedule your barber visits beforehand

Subscription Services:


Birchbox for Men

Black Socks

Mindset Takeaway:

Build habits into your day that will help you dress and look better regularly, day after day, so that dressing well doesn’t require special effort.


The Personal Image System (Master-Level Course on men’s style)


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