in: Featured, Outfit Guide, Style

• Last updated: July 7, 2023

A Man’s Guide to Style Transition: 6 Steps to Start Dressing Like the Man You Know Yourself to Be

Vintage man helping another man to wear a blazer.

Over the past two years we’ve written quite a bit here at AOM about how to dress better; but one thing we haven’t addressed is the mindset necessary to carry out changing your personal presentation.  Having consulted with hundreds of men on improving their appearance, I’ve discovered that most are ready for change, but many are at a loss as to how to go about it.  They know they want to transform their outward appearance, they know they want to enhance their personal style, but they are unsure about how the process will work and if the transition will be successful.

Some might say it’s because men are resistant to change; this is absolute nonsense.  As men we love to travel and try new foods, we purchase new cars and homes, move our relationships from dating to marriage, and take on the role of father to our children.  We embrace change, and in many cases seek it.  No, the real problem is not the change but instead the uneasiness we feel during the transition.  And the longer this awkward transition period takes, the harder it is to institute a permanent change.

The key to successfully revamping your personal appearance then is to make the transitional period as painless as possible.  So how do you go about changing the way you present yourself to the world?  Here are six powerful steps to ensure your wardrobe transformation is a success.

1.  Make a commitment to change your personal style

Once you are sure you want to step up your personal style, make a commitment to this change.  Commitments are made in various ways, but one of the most powerful ones I have seen is when a man verbally tells those close to him that he is going forward with the change.  And don’t limit this to your wife or significant other – the commitment becomes more likely to be fulfilled when you let your friends know as well, and making a written commitment with a set date can more than triple the likelihood you’ll follow through.  Of course you risk not making your goal – but that’s the whole motivator here, the fact that we strive to be consistent in our word.

2.  Get specific about how you’ll rebuild your wardrobe

When refining your personal presentation, you need to have a plan and know exactly how you are going to make to make the change happen.  Seek to eliminate cluelessness by laying out the step-by-step details that make up your plan of action.  Include the exact type of garments, which order you’ll acquire them in, and how much you are willing to spend.  With the commitment to change in place it becomes a matter of locating a trusted merchant and taking action.

One of my most successful series of articles here at AOM was the “How to Build your Wardrobe” series.  The reason so many men enjoyed these articles was that they went into the details; they spelled out exactly what it takes to build your wardrobe.  We didn’t leave it at “you have to dress nice;” instead, we defined what it meant to dress professionally and gave you a layout of exactly which business suits, dress shirts, and dress shoes you should have in your closet.

Finally, when getting specific, understand your needs and do not underestimate the importance of educating yourself on menswear.  Besides the great content in the Art of Manliness’ Archives, you can reach out to clothiers offering free style consultations, men’s image consultants that specialize in helping you look your best.

3.  Eliminate Barriers to Change

Oftentimes we sabotage our own efforts to institute change.  When looking to dress better, remove small obstacles that might trip you up.  Look to shape a path that enhances the journey and makes the process simple.  Here are just a few examples of shaping the path to dressing sharp.

  • Lay out your clothing the night before; by having everything neatly arranged and coordinated there is no thinking or looking for misplaced items in the morning.  Even if you are running late, it’ll be a snap to dress sharp in minutes.
  • Set a time on Sunday evenings to shine your shoes; with three pairs in your rotation you should be able to make it through the week with only touch-up brushes.
  • Iron all of your shirts at once; it takes you as much time to set up the iron and board as it does to iron one shirt – by knocking out six shirts or more at once you save yourself 15 minutes every week over ironing each shirt separately.
  • Invest in simple and functional gentleman’s accessories such as galoshes and an umbrella. Then place them where you can find them; when you need them they will pay for themselves after a few uses, especially when protecting your footwear from damage on a rainy day.

4.  Build on your strengths and incorporate something unique to you

Build your personal style on your strengths and incorporate aspects of style which will make the style of the clothing truly yours.  Are you a huge Lakers fan?  Look to have a purple and gold lining sewn into the inside of your sport jacket.  Have you followed the New York Yankees since you were a kid?  Then work like the Yanks by opting for pin-stripe suits.  A bit silly?  Yes, but having fun and focusing on making your clothing unique to your personality will make you more likely to wear it and more comfortable in it when you do.

Dress Shirt Collar with Black Stripe.

Having fun with a shirt collar style!

5.  Change your mindset

Logically we know that dressing professionally leads to stronger and more positive first impressions; emotionally however, we resist trading in our khakis and polo shirts for dress trousers and sport jackets because we are worried how our colleagues will react to our dressier appearance.  And more often than not, emotion will win the battle.  The key then is to use emotion to change your mindset; although the decision may be based in logic, by tying it to an emotional anchor we create a much more powerful and consistent pull.  Example – Instead of dressing sharp to increase your chances for a promotion, dress well because you want your wife and son to see you the way you see yourself, as a leader with great potential.  The stimulus of dressing as a positive example for your family is more powerful than that of a potential pay raise.

6.  Just Get Started

The hardest part for many of us is just getting started.  We wait, analyze, and then wait some more.  But understand that not making a decision is in itself a choice – your decision not to purchase that custom suit six weeks before the interview means you risk settling for an ill-fitted off-the-rack garment 4 days before the big day.  Avoid analysis paralysis by setting a timeline of when a decision has to be made; make an educated decision with the information you have available and then make your decision.  Missed opportunities are just that – missed.

One tip I give clients looking to change their entire presentation, but who are hesitant to take the plunge, is to have a single outfit perfectly tailored and ready.  Then hold off on the rest of the wardrobe.  After they realize they are wearing the same outfit again and again because they look great in it and it feels good, they are ready to expand their closet by building off this core ensemble.   The hard work is in getting the started – once you know what sizes fit you or a tailor has your body measurements, you can simply order everything you need and know for certain you’ll have the fit down.


Transforming your personal appearance isn’t especially difficult; what makes it hard is our unwillingness to address the transition clinically.  Once you commit to dressing better, a well laid out plan of action that’s divided into small executable steps and supported by the proper mindset is more likely than not going to succeed.

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Written by
Antonio Centeno
President, A Tailored Suit
Articles on Mens Suits – Dress Shirts – Sports Jackets
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