Hey gents,

Think back to when you first started on this style journey. Remember all the uncertainty you faced? All the questions that arose and the seemingly endless number of options that laid before you. Sorta made your head spin, didn’t it?

Maybe that sounds like your situation right now. Perhaps you’ve just started on a style reinvention of your own, and it’s such a new world that you have NO IDEA where to start, or how to distinguish right from wrong.

Or! Maybe you’ve already been on this path for a couple weeks or months, but you’re still learning and realizing it’s an ongoing process.

Know that wherever you are in this whole process, eventually, you will be sidetracked. There’s also a good chance those closest to you (maybe even you yourself) will sabotage your self-improvement efforts.

Sounds crazy, but it’s true, and it often happens without the guilty parties realizing they are doing it. It’s important you recognize when this is happening and do your best to avoid the situation all together… especially if it’s you who’s doing the sabotaging!

Here are the kinds of things that can sidetrack and sabotage your efforts at style self-improvement:

  • Listening to negative talk, feeding yourself negative thoughts
  • Thinking you’ll never get the hang of it, or thinking too much and overanalyzing everything
  • Making excuses (“I don’t have money,” “I don’t have time,” “I don’t want to look ‘metro'”)
  • Letting people’s opinions sway you from what you know you like or know is the correct way to wear something

Some solutions

There’s a solution to every problem. Here are some ways you can avoid losing focus and getting sidetracked when attempting to up your style game.

Keep it simple

Always remember: It’s not that serious. It’s just clothing, not a PhD dissertation. Pick an outfit and go with it.

Uncertain about a particular color combo? Try it out for one day and see how you like it. Turns out you hate it? Don’t pair those things up again and instead try something else the next opportunity you get.

One thing at a time

You dont have to know everything right away. You don’t have to own the ideal wardrobe all at once.

Focus on improving one item in your closet at a time. Do you wear jeans a lot? Start there. Get your one pair of serious denim (you know, the dark inky kind).

Wear suits to work every day, but you’re still throwing on that number you bought for your eighth grade graduation? (Yeesh, you still fit in that thing?) Save some of that hard-earned cash and invest it in a suit a working professional should be wearing.

There’s never enough time or money

There’s never enough time unless you proactively make time to give something the attention it deserves. There’s never enough money unless you proactively save money to invest it in something later.

Common sense, right?

Think of it like weight loss (or gaining muscle). You probably have a thousand things you must get done during the day, so if you don’t proactively make time for the gym, you’ll just never go. Why? Because you have a bunch of other stuff to keep you occupied (work, friends, YouTube) and all hopes of going to the gym will just fall by the wayside.

Same goes for your money situation. If you’re not proactively saving (for anything, really… not just a new suit or your first pair of grown-up leather shoes), your money will go out the window with small purchases here and there.

You have to make a proactive effort to see any results.

Here’s an easy proactive task you can complete tonight. Before going to bed, take five minutes to figure out what you’re wearing the next day. Actually take the clothing off the rack and lay them out, or hang them in a separate section of your closet.

In case you have a hectic morning, that will be one less thing you have to think about. Since you did yourself a favor and set everything up the night before, you’re less likely to throw on the same old clothes you’ve been wearing forever out of convenience.

Use both positive and negative reactions to fuel you

Most likely you’ll be getting great reactions from your friends, coworkers, and family who notice your slight changes in wardrobe and style. I get emails all the time from gents who say the people around them have noticed the improvements, and that can be really motivating!

Not everyone’s so lucky, unfortunately. There’s a chance that the people surrounding you won’t understand why you’re trying to dress better, or why you suddenly care about how you dress and what you look like.

Don’t let the naysayers get you down. Oftentimes people project their own insecurities and shortcomings on others because they can’t make their own lives better.

Instead of listening to them, focus on learning and getting better, and if you improve a little each day, dressing better just becomes natural. It no longer will feel weird or trying, it will just be you.

Also remember your reasons why you want to dress better in the first place. Sometimes it’s for more outwardly, vain reasons… but mostly it’s so you look and feel better and more confident. Confidence is the name of the game, buddy!

Listen to those you look up to (but still take all advice with a grain of salt)

Take advice only from people whose style you admire, and whom you know just get it. Don’t listen to your parents (sorry guys), schlubby friends, or terribly-dressed significant other telling you what to wear, or saying that you look “weird” in your new clothing. If they can’t put themselves together, what makes you think they know what’s best for you?

On top of that, you’re a grown ass man. Other people shouldn’t be telling you how to dress. Ultimately you’re dressing for yourself, but in case you need that validation from others, get a sampling of reactions from a wider sample set.

Better yet, find that dude whose style you dig and ask him what he thinks. If he thinks your choices are terrible, ask him for suggestions on what he’d do differently.

Once he gives them to you, decide if you agree or not. If it’s the latter, then do whatever the hell you want. Who knows, his advice might be crap and not apply to you anyway. Use your head and listen to your gut.

At the same time, know that any style advice you get may not necessarily be wrong. It could just be out of your comfort zone. There’s a difference.

Remember why you started caring in the first place

Dressing well is all about building and projecting confidence, and presenting yourself well to those around you. It’s about being educated enough to make conscious decisions based on the rules that exist and the ones you decide to break.

Dressing well only happens once you take the time to create your own personal style. –  click to tweet this 

Don’t let others get in your way, and definitely make sure not to get in your own way. Even if you feel like there’s a long journey ahead of you, take it a day at a time, or even one piece of clothing at a time, and go from there.

Anything worth doing takes work and dedication.

Help (or a second opinion) is never too far

You always have EG! In case you have questions or need clarification, you can email me here. I read every email I receive.

By the way, since we’re on the subject of making progress with creating your own personal style, I might as well mention my own solution, right?

Over 650 students have gone / are going through my self-guided eBook, The Effortless Guide to Graduating Your Style, with plenty of success (according to the emails I’ve received, at least).

I asked a few readers their thoughts once they completed the book. Here’s a snippet of one reply:

“I love Graduating Your Style. It’s a step by step guide to looking good with minimal effort and minimal spending. It will save you countless hours and hundreds of dollars trying to figure out how to look good on your own.” – Ryan, CA

This may or may not be the kickstart you need, who knows. In case you’re curious, you can read more about it here: http://graduatingyourstyle.com

Your turn

Hope these little morsels of encouragement help you to keep going in your journey to improve your style and grow up your clothing a bit.

Have you had success following and applying some of the tips we’ve dispensed on the site? I’d love to hear it. Let me know in the comments below.



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2 Responses

  1. TJ on

    Changing and “graduating” your style is something that takes time. I’ve been working on my style for about 2 years now, and I am nowhere near finished (mostly for financial reasons) but I am working on it everyday. I’ve had some missteps and errors along the way but I have learned from them. When I first started out, I had no idea what I was doing but I worked at it and I am light years from where I was 2 years ago. It takes time and work, but anything worth doing does.

  2. Erwin Barabas on

    TJ summed it up very well, I am not as far as he is – started to work on this about a year ago, but I got the same feeling – I’m light years from where I was 1 year ago.

    Friends noticed the change and most of them told me they like it.