Figure out THIS for your style to fall into place!

August 19, 2023
I want to hammer in a point regarding men’s lack of attention when dressing. Here’s my tip — if you don’t know much about style, keep it simple. And when I say simple, I don’t mean a graphic tee and baggy cargo shorts with flip-flops. Or even worse, acid-washed jeans, a cheesy button-up, and a vest.

One of the best investments you can make is in a good pair of jeans, cool boots, and a bomber jacket. Don’t over-complicate style. Sure, style is totally personal, but by focusing on fit, clean/minimal clothing, and classic/timeless pieces, you can level up in three simple steps.

Before we talk about leveling up, I want to address three critical components because men tend to over-complicate when trying to become more stylish. They try too many new/trendy styles that go out of fashion too quickly for them to really learn. So, stick to these basic rules of thought:

Buy clothing that fits. If I’ve said it once, I’ve said it a thousand times. Buying clothing that fits will elevate your style and solve most of your wardrobe issues. Most men tend to buy clothes that are too big. Think about it — you will look 1,000 times better in a $50 outfit from H&M that fits than a $1500 outfit from Ralph Lauren that is too big. Figure out your fit, and the rest will easily fall into place.

Wear clean and minimal clothing. Avoid too many details, such as prints and graphics. As I have mentioned many times, avoid graphic tees, sports jerseys, overly distressed jeans, and the like. Dressing clean and minimally will elevate your style to a more refined and mature level. Think white, black, gray, navy, khaki, and olive solids. Think dark wash jeans with minimal distressing. Think navy or gray suits. All of these create a fantastic foundation to start, which you can add in color later.

As I have recommended before, stick with timeless classics. Unlike women’s constantly changing and evolving styles, we have the advantage of having a more stable style. When starting on a quest to elevate your style, stick with a classic yet versatile base that includes the following:

So now let’s get to the meat of LEVELING UP your style. The first step is inventorying your wardrobe in three categories: shoes, pants, and shirts. Sure, there are other wardrobe categories, but we need to break your wardrobe down as basically and simplistically as possible. Think about it — you work with these three categories daily when making outfit decisions.

Next, you need to determine which level your style falls into by looking at yourself with a critical eye: Level One, Level Two, or Level Three. I know you want to fit in with your friends, family, and co-workers – so I assume, at this point, you are fitting in by dressing consistently with how others dress around you. Correct? So, where do you currently fit with your style?

Level Two – STYLISH

Now you know the inventory of your three categories -and- you know your style levels for each of those categories. Elevating your style without being detected is as simple as stepping up a level! Step up only one level in only one category at a time. Guys get into trouble when they go from shopping at the unsexy section of Sears to dressing like a GQ magazine model. Yes, people around them will notice. Be more cunning and methodical than that! Here’s how …

When meeting your buddies, you usually wear a pair of sneakers, baggy acid-wash jeans, and a screen-printed standard tee shirt. We know that every category is Level One (NOT STYLISH). Everybody you’re meeting is wearing practically the same unstylish look. So what do you do? Simply pick one category and move it up one level.

  • Start with shoes, for example, and bring them from Level One to Level Two. You’ll be wearing the same shirt and jeans as everyone else – but your shoes are leveled up one level. Others may not notice or comment about your new shoes. Lo and behold, you, my friend, have not been excommunicated for wearing more stylish shoes.
  • After a period of time, you will move to another category up a level. The next category may be pants, for example. Instead of your acid-washed jeans, you’re wearing dark-washed jeans. BUT you’re wearing the same shirt.


Over time, your entire wardrobe will move up a level. When you complete Level Two, you’re now STYLISH and can move to the more risk-taking FASHION-FORWARD. Proceed methodically by starting with one category and moving it up — and so on and so forth.

Another example is when you’re at work, you’re sporting unstylish orthopedic shoes for support & comfort. You wear baggy pleated cotton khaki pants and a baggy shirt with button-down collars. The level is equivalent to a negative one — it’s just hideous and heinous. One category at a time, you’re leveling up.

  • Instead of those orthopedic shoes, you’re wearing something a little more stylish but still comfortable & supportive, perhaps with orthopedic inserts.
  • Next, level up the pants by shifting to a fitted flat front in a nicer fabric like microfiber.


Your choices are just a more stylish version. Nobody will notice if you do the leveling up one by one and category-by-category! This method works in any situation or group setting.

These seemingly little changes can make a significantly big difference. By systematically replacing those unstylish category pieces with elevated stylish options, you will see that your entire style game is elevated over time. Your entire style and wardrobe will move up levels, and you will feel great. It won’t be easy and sometimes a bit scary, but you can do it! I promise! And you are going to love the results!

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