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

by Antonio on August 12, 2010 · 14 comments

in Dress & Grooming, Style

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, or menswear specific blogs written by regular guys such as Made to Measure NY & Scientific Style; both of these are great for supplementing your education and inspiration.

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 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.

Written by
Antonio Centeno
President, A Tailored Suit
Articles on Mens Suits – Dress Shirts – Sports Jackets
Join our Facebook Page & Win Custom Clothing

{ 14 comments… read them below or add one }

1 Greg M August 13, 2010 at 12:55 am

I made a conscious decision to stop dressing like a 30+ boy and start dressing like a man three years ago when I ditched my douchbag haircut for a classic one and re-vamped my wardrobe. The results have been amazing. The reaction of those around me is completely different- whereas I used to be ignored when I walked into a company or store I am quickly approached by the staff to assist me in my business there.

I feel more confident and actually more COMFORTABLE in attire and accessories that are selected to properly match the way that I live. You really need to take an honest look at yourself when getting started, but the results are beyond belief.

2 Antonio August 13, 2010 at 7:42 am

Greg – Thank you for the kind words and for sharing your example of positive change brought about simply by paying more attention to the way we present ourselves. It’s such a simple but underrated thing – and it completely under your control, unlike many other things in life!



3 James August 13, 2010 at 11:03 am

Great article. I’m the first to admit that I’ve not made dressing sharply a top priority in my life. I used to, but I let it slip as more and more “life” crept into my juggling act. Several months ago, however, I was noticing that my crew were dressing like slobs. The entire department (that I manage) started looking sloppy, and that alarmed me, because we do very precise work in an office of people who all must look good and sharp at all times.

So, I upped my style. I bought a suit. I acquired new shoes. I sought out several killer sales and got a few pairs of very nice pants and shirts. Bought a couple ties, and, found a couple of older ties from my original collection that work great.

What happened? Slowly, without me having to say a word, my crew upped their style too. And, their desks became cleaner; they carried themselves with more confidence.

There are several take-aways here. I was chiefly interested in the subtle influences we have on those around us, simply by the way we dress. When you walk toward someone, you are already communicating with them. You are communicating by your posture, the way you walk, the way your eyes are set, and, by the way you dress. In essence, I was telling my crew that “the bar has been raised”.

Another important take-away is that “everything matters”. How you look on the outside is another piece to becoming a whole man. Yes, it matters on what’s going on on the inside, but changing your wardrobe and upping your style helps immensely.

I have to run, but, just wanted to say thanks for such a great article.

4 Paul August 13, 2010 at 12:38 pm

I live in the Phoenix area where the definition of getting “dressed up” is putting on a pair of socks. I admit, though, I truly miss dressing the way I did when I lived and worked in the San Francisco area in the mid-80s through mid-90s. I agree that the way you dress affects the way you carry yourself. Perhaps that’s what I’ve been missing for the past few years. I’m a self-employed writer working from a home office so my daily wardrobe, especially on 110 degree days like today, is typically shorts, a tee shirt and flip-flops. Most of the time I feel like a slob but in my mind I can’t justify the time and expense of sharp clothes to sit here in my office, by myself, all day. I often think that if I improved my appearance I might also improve my attitude, confidence and daily performance, but justifying that first shopping trip and thinking about the return of dry cleaning bills and ironing shirts stops me in my tracks every time. Anyone else have this problem? Any advice?

5 Erick August 13, 2010 at 4:13 pm

I made a decision to change the person I was about a year and a half ago.I was fat, out of shape and drinking far too much. I was about to become a father. I wanted to be healthy enough to be around for my son and began going to the gym and what was a chore became a passion. I changed my body and felt great. But then I realized I not only wanted to be there for my son, I wanted to be an example for my son and roughly 5 months ago I stopped spiking my hair, got a hair cut, and started caring about the way I dress.

Living in Portland, OR and working at a company who’s first line on their job applications is “A suit and tie aren’t even an option at x-company” dressing in anything but teva sandals, shorts and a ratty t-shirt that has some saying on it is standing out in the crowd. I chose to stand out, I don’t wear dress slacks but I wear very nice jeans, polo shirts, as well as a variety of leather loafers. I comb my hair and shave every other day, you’d think some of these people believe that a razor is giving into some sort of societal pressure.

The result of course was initially a lot of “Wow going somewhere special” to receiving various compliments that basically can be summed up as “I like the new dapper look.” My wife admits now that she much prefers this look to my old “bad boy” look and that she loves the confidence I carry around now. So I’d like to thank Antonio and The Art of Manliness as I read all of the Wardrobe articles he has written and taken careful notes. They have been an incredibly deep resource in assisting me in my change. For anyone considering a change I’d say that #’s 5 and 6 were the biggest ones to me. Get over what people will think, and have a plan.

6 Mr Ed August 14, 2010 at 2:17 am

The only thing I’d beg to differ about is: if you shine your shoes only once a week, do it Saturday evening–not Sunday evening!

7 saad August 14, 2010 at 7:50 am

Wow, amazing coincidence you posted this, because I am doing exactly this “mindset-change” project, which I started last week. I’m recording my progress on my blog w/ a photo diary.

8 dk August 14, 2010 at 8:30 am

This series has been very interesting to me – last December I changed jobs and the corporate culture I was used to was no longer necessary. I left a company that experienced the casual freedoms of the dot-com era where the norm was jeans and teeshirts and was given the opportunity to make myself over by accepting a technical position in management. So I pulled out and reviewed my business wardrobe and began filling in the missing pieces. Initially some laid back upper management folks were resistant to my more formal appearance – some might even use the phrase “animosity” – but in time they were won over. This trans-formative act extended beyond myself, as well, and I am pleased to see that other employees are more inclined to follow my lead with formal attire at the beginning of the week, business casual towards the end of the week, and, naturally, casual Fridays. I have always preferred a collar and a tie to a teeshirt and I was able to redesign myself in the process which ultimately has improved the company’s level of professionalism.

9 Days and Adventures August 14, 2010 at 10:15 am

I love what you wrote about mindset. Great insights.


10 Declan M August 17, 2010 at 10:14 am

Great article. I made the decision to stop dressing like a slob about 6 months ago. I started by making a list of all the items I would like to have, and then set about making a plan on which order to buy them. It has been going slowly so far. I am at university and money is pretty tight, so I haven’t been able to move as quickly as I would like. I’m still dressing in a less than desirable fashion, but at least my mind set has changed and I’m working towards something. If anyone has any tips on how to dress well on a budget then post them up!

11 Joe August 18, 2010 at 10:16 pm

@Declan: If you’re looking for ways to dress well on a budget, allow me a cheap plug and suggest Dappered.com It’s all we do. Great article by Art of Manliness as always. Best of luck Declan with the pursuit of taking a little more pride in how you present yourself.

12 David Smith August 29, 2010 at 5:45 pm

I think it was Hardy Amies that said, “A man dresses well, simply because he wants to.” The hardest thing is to make the decision and act on it.

As a teenager in London in the early 80′s, I was incredibly concerned with what I wore – obviously this is easier without the responsibilites of adult life, marriage, fatherhood, etc – but I cared and made an effort. However due to all of the above, over the intervening years I simply lost my mojo!
I’m now 42 and a highways engineer by profession; my job is about 70% office based and 30% site visits. I used to dress like I was on site visits 100% of the time… About 18 months ago I read Nicholas Storey’s book, “History of Men’s Fashion.” Not to put too fine a point on it, it completely changed my attitude to how I dressed for work. I decided I’d had enough of looking like one of my operatives and this book helped reignite my love of classic British tailoring and looking smart and stylish.
I have to say it was quite a shock to many of my colleagues but despite this, the reaction was almost universally positive, particularly amongst the women! I am now regularly complimented on my sartorial choices and these days people comment if I’m NOT wearing a suit and tie! (My office has an unofficial casual Friday and I always make a point of wearing a suit in protest just for the sheer hell of it!)
The key thing I would say, is to have the courage to go for it and don’t be afraid to experiment with colours and different combinations.

I’ll end with another Hardy Amies quote: “A man should look as if he has bought his clothes with intelligence, put them on with care and then forgotten all about them.”
I reckon that neatly sums up the attitude one should aim for.
p.s. If anyone asks, I tell them to check these out:


* Esquire’s Handbook of Style
* History of Men’s Fashion – Nicholas Storey
* Gentleman – Bernhard Roetzel
* Sharp Suits – Eric Musgrave
* The Englishman’s Suit – Hardy Amies

* GQ
* Esquire
* The Chap – http://www.thechap.net

(Keep up the good work at AoM, superb website!)

13 Chapman Bags March 3, 2013 at 3:37 pm

I think another tip is to go with what works for you. Some very sporty men can’t just jump into a suit and expect to look at ease. At times a gradual change is best, and even style consultants can miss this.

14 Eric December 9, 2013 at 10:30 am

I can truly say that dressing well does something amazing to your confidence level. When I started dressing well I started to feel like a MAN, people started to look at me like a man and my wife started treating me like a man and wanted to do nothing but follow my lead, and I’m only 25! Thank you so much for this article and this website for that matter for bringing back the Art Of Being a Real Man. Much appreciated.


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