One of the most important skills you can learn as you develop your own sense of style is how to judge whether something fits you. I don’t mean just physically (though that’s critically important), but also whether something properly suits your personality, character, and lifestyle. For example, a cutaway collar might frame your face very well, but if you’re a stodgy academic who is hoping to be thought of as an intellectual, perhaps a button down collar is more suitable.
Figuring out how clothes should fit is one thing; figuring out whether they suit your personality and character is something else entirely. That part requires a lot of self-discovery, honesty, and time. Unfortunately, when it comes to the task of finding clothes that suit your character, you can easily be distracted by barrage of blogs and magazines telling you what’s cool this season, what’s big in Japan, or how to pull off that “Italian sprezzatura” look that everyone is raving about. Couple that with professional product shots and good looking models, and you can be drawn to certain clothes for all the wrong reasons.
One thing I’ve found helpful is to be conscious of whether you’re buying something just because it’s well designed. Remember that there are hundreds of good looking pieces every season. Indeed, there’s rarely a week that goes by where I don’t see at least five or six things that I think look great. However, just because a piece of clothing is well designed, and perhaps even fits you well, doesn’t mean you should buy it. You should stick to the task of developing a focused, coherent wardrobe that clearly express who you are, not just build a collection of good looking clothes.
And although it’s counter intuitive, I’ve also found that it useful to have a very narrow and defined set of style heroes. People you think are maybe more aligned with your personality, character, and lifestyle than others. Of course, inspiration shouldn’t be the same as emulation, and at some point, you’ll naturally find your own voice, but it can be helpful to be clear about what looks you’re going for.
Thoreau once said, “A man is rich in proportion to the number of things he can afford to let alone." It’s important to recognize when something looks great, but isn’t necessarily right for you. Shop slowly, let your clothes reflect your body and personality, and know when to leave something alone.