Footwear Starting from the ground up, appropriate-fitting footwear is the first step to dressing sharp.If you’ve never owned really good shoes before, brace yourself and get ready to pay a significant amount of money for well-made, classic footwear. Dress to Look Older If you’re still wearing clothes that scream “student days,” you’re going to be treated like a boy with no experience in the real world. Buck the trend, age your look a little, and get the respect you deserve from older men. Ignore Fashion Trends. Most young men don’t have the budget to buy new pants every month or two — so stay away from pants that are only presentable during an “in” season. Stick to classic clothing staples for the core of your wardrobe and avoid anything that’s too far out on the cutting edge — even if you see something that makes it look good. Have at Least One Good Suit in the Closet If you’re in a field where you’re going to wear one regularly you should look for a variety of colors and styles; if you just need a single suit for infrequent dress occasions stick with a classic single-breasted, two-button suit in charcoal gray or navy blue. If you’re buying off the rack take the time to have the suit adjusted. A few department stores still offer the service, but you’ll more than likely need to find a tailor independently.