Some style moves are classics & will never let you down (looking at you, white t-shirt). And some moves are always a mistake - and easy to make when you're new to the game. True, mistakes are the only way to grow, but here are a few you can skip over to move straight to style level 2.
  1. Over-emphasis on your original reaction
    Like anything new, styling-up might feel a bit awkward. Many men I've helped to style-up initially felt uncomfortable in a shirt that didn't hang like a tent, or slim jeans that revealed the shape of their legs. I suggest that they take their new gear home and model it for their significant others. If they are still miserable, they can return everything, no harm, no foul. I often get a text that evening saying, "She loves it!"
  2. Over-emphasis on "cool" details.
    "Look! These shoes have crazy stitching! This sweater has epaulets! This t-shirt has a cool graphic! These jeans have a cool design on the back pockets! This jacket has cool patches! This watch has a cool dial that tells you the temperature in Peru! This shirt has a swatch of color along the collar and above the pockets!" GREAT! But how does it look on your body?
  3. Over-emphasis on color
    Just because you like to look at a color doesn't mean you look good in it. My favorite color is orange. I used to have orange sweatshirts, orange shoes, wore an orange scarf. One day, walking on Coney Island, my friend and I passed an old lady dressed head to toe in fluorescent orange. My friend said: "That's you in 50 years." That ended the "Orange Phase."
  4. Over-emphasis on brand names
    In my early styling-up, I would buy stuff just because it had a Diesel tag, Marc Jacobs tag, Ted Baker tag. As a result, I had a lot of weird outfits that didn't really fit me. I needed to learn to MAKE my look - not to BUY my look.
  5. Over-emphasis on whatever's trending
    There's an undeniable rush when you slip into an outfit that you're seeing in GQ or out on the street: a feeling of "I can do this, too!" But pay attention not only to how it makes you LOOK, and notice how it makes you FEEL. Maybe dropped crotch sweatpants aren't for you.
  6. Over-emphasis on "dope pieces"
    Style is not about a pair of shoes, a watch, a cool jacket: it's about the gestalt. From my early stages of the game, I own black Star Wars Adidas that looked so dope on the shelf, but which never went with anything I've ever worn. I haven't had the heart to give them away because the sole says, "If you only understood the power of the dark side." But let's just say I recently wore them camping because I didn't want my actual shoes to get beat-up.
  7. My main piece of advice: whatever you put on should bring you joy.
    I helped this young man style-up before his Bar-Mizvah. He'd never worn a blazer in his life. Look at his face. That's what you're going for.