How does a man learn to become classically stylish? If a guy wants to know how to look good on any given day, it doesn’t take much. A quick Google search or scan of Instagram can give even the worst dresser an idea of what to slap together. But that isn’t goal.

How Does A Man Learn To Become Classically Stylish?

You’re not learning to just mimic what others are doing, you’re learning to find a style that best fits you. So, how does a man become stylish?

If you Google the definition of Stylish, you get this:

having or displaying a good sense of style.
“these are elegant and stylish performances”

Or if you rather, Fashionable:

characteristic of, influenced by, or representing a current popular trend or style.

Style is also about context.

Above all, becoming stylish, just like becoming fit, or becoming more confident, is something that takes time. Style isn’t necessarily about what you’re wearing, but about how what you’re wearing looks on you. Another thing to note is that the clothes must compliment your body type, while looking good at the same time.

A perfect example of this is a friend of mine that bought a mesh shirt men years ago to go on a first date. He was overweight, lacking confidence, and had no idea how to dress, period. He thought a mesh shirt would look good, because he’d seen others wear it. It didn’t dawn on him that these guys were fit, and wearing them to impress other men, not girls, like he was.

The above definitions I gave were to show that if you’re stylish, you know what looks good on you. You have your own sense of style that’s unique and timeless. Similarly, if you’re fashionable, you just keep up with the trends, you’re looking online to see what’s new and hot.

  • Make sure you’re eating right and hitting the gym. The clothes will not look good on you if you’re not working on improving your physique.
  • Get your measurements
  • Go to as many stores as possible and try on as many different outfits as you can. Mix old (vintage + consignment) with new (modern and fashionable) and see where it takes you.
  • Feel the quality of the clothing. How does it feel on you? Is it heavy? Light? What fabric is it made from?


And a few other basics.

  • Learn to visualize yourself wearing the clothes. I no longer have to try on anything that I buy. I can visualize and know right away if it’s going to look good on me or not.
  • A phone is not a watch. Remember this. Learn to add accessories to your outfit.
  • Look at the colors you’re wearing closely. Look at how they “bounce” of your skin. How does it look?

Furthermore, some more important rules:

  • No baggy clothes
  • No ripped clothes

Finally, with this in hand, get out there, hit the gym, get your measurements, and then start shopping. And like I always say, it’s quality over quantity.


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