Here we go @jon! (Not that you really need this, I suspect!) I'm gonna ask @katiegoodwin for an assist on this because she knows everything about FIT, which is, you guessed it, EVERYTHING.
  1. Educate yourself.
    There is so much information and inspiration available online these days, all you have to do is pay attention. I'm obsessed with GQ magazine (the print version), which has tips and inspo galore, and also, which sells the dopest shit AND has good content in The Journal>Stylepedia or The Journal>Style Icons or The Journal>Style Advice Q&A, which is SUPER helpful.
  2. It's all about FIT.
    Same's true for the ladies: if it doesn't fit perfectly, it doesn't look good, no matter how much you spent on it. Make sure a jacket fits in the shoulders when you buy it; that's the hardest/most expensive place to have it altered.
  3. To quoth Master West: "You need to crawl 'fore you ball."
    Start by mastering the basics, baby. Find the perfect pair of jeans, boots, and sneakers. (@jonathan made a list of his favorite, all of which I approve of!) Get a t-shirt that fits your body and and lifestyle AND makes you feel good. Stick to simple cuts and washes and natural fabrics (cotton > synthetic blends or polyester). Keep it simple, sweeties. We can talk print-on-print suits later.
  4. When in doubt, ask yourself: "What would Steve McQueen wear?" Feel free to sub in Sir Michael Caine or A$AP Rocky or Justin Theroux or LeBron James or whomever you like.
    And then just steal their style. Seriously. It's what great artists do!
  5. Wrinkles = Not Cute
    For many men, half the battle is just not wearing wrinkled clothes. Downy Wrinkle Release Spray is great for most things, esp t-shirts. Get a steamer (better than an iron); it's easy to use & worth the investment.
    You're welcome!
    Suggested by @jujujerni