Finding Your Style 101

Throughout my adult life I have been approached by many men who have asked me to help them with their dressing. “How can I dress better,” they would ask, and to be honest, I did not always have a response. Not because I don’t know where to shop or how to put an outfit together, but because, to me, dressing is an extremely personal endeavor; even the state of dressing and getting undressed is one of the most personal experiences one can have. As such, how could I be of assistance? What I realized is that it wasn’t that the men who were asking me were just asking me to shop for them. What they were really asking me to do was help them figure out their style aesthetic and ways they could execute the most stylish version of themselves. How does one do this; well to give guys a head start on answering that (and adjacent questions) I have drilled down the four things a man should consider when figuring out and executing on his style.

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Who are you?

How would you describe your personality? What do you enjoy doing? How do you show up in the world? All of these things matter when starting your style journey. Now obviously many of us are very complex people that might show up differently depending on the circumstance. For instance, some of us have professional day jobs and more creative passions we pursue on the side. However, if you consider yourself a very straight forward, no nonsense individual, an overly complicated wardrobe or super loud aesthetic may not feel the most authentic for you.

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What is your lifestyle?

Lifestyle should be a key consideration as you start your style journey. What type of city or town do you live in? What types of activities make up your social calendar? What is your work environment? Do you travel often and if so where and how? Ideally the wardrobe of a well-rounded man will have several key staples that everyone, and I mean EVERYONE, should have – a good dark suit, quality dress and casual shoes, a crisp white button down, etc. However, how many of these basics you might need, as well as if you should own additional items like your own tuxedo or a collection of dinner jackets really depends on your lifestyle. For example, I own a decent collection of eveningwear, but at one point (pre-pandemic) I was attending, on average, one black-tie or formal event a month. If you live in a more casual manner, your wardrobe should reflect that.

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What catches your eye?

Once you have the aforementioned pieces down, you can begin to focus on the fun part - the pieces make you the most excited. What styles, colors, patterns, materials are you most drawn to when you are in a store? What celebrities or athletes do you tend to refer to when thinking about looks you would like to wear? A while ago I began to screenshot photos of looks that I found super stylish, no matter if their were on the runway, on a celebrity, an influencer or just an everyday person. In going through those looks I was able to identify themes such as particular color schemes and silhouettes I was clearly drawn to more than others. I was then able to pinpoint designers or brands that were consistent across these photos, and if those were out of budget, research more affordable brands with similar aesthetics.

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Try, fail, then try something else.

Trying different things is important when developing your style. Now this might not always end up going well (looking back at pictures from college and my early 20s is cringy to say the least), but ultimately this experimentation was necessary to help me hone in on what worked and did not work for me when it came to my style aesthetic. As I began to settle into my life and career, the needs of my wardrobe became more evident, which also aligned to who I was growing into as a fully formed adult. 

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