Wear Well Made Shoes and Suits That Fit. Ok, this might seem superficial, especially after #2, but bear with me. Like many young men, I went through a phase of wearing XL everything — in spite of weighing 165 lbs. This lasted until my late 20’s when I bought my first tailored suit and real leather shoes. The difference in how I felt and how people regarded me was not subtle. It was like putting on 10 years of stature and prestige. So, don’t waste money on cheap suits and shoes. You’ll just look…cheap. Instead, get 2 impeccable suits (1 navy blue, 1 black/charcoal) and two pairs of Italian or English shoes (1 brown, 1 black), and wear the hell out of them. ProTip: Wear the brown shoes with the blue suit, and the black shoes with the black suit, for god’s sake