Unless you are in the mafia or a CEO skip the black pinstripes.

Color is the place where things can really get confusing and where most of us are clueless. Make it easy on yourself at first and just stick with white shirts and blue/black/charcoal pants and jacket. Add color with your tie and avoid the outlandish ones. The overall look will be classic.

Build your wardrobe with solid basics in classic cuts and with proper care they will last for years. Get shirts with drop point collars, not button down. Button down collars are a casual cut. They were made for polo players to keep the collars from slapping them in the face. A drop point collar, even without a tie, gives a nice bit of dressing to the neckline.

Dress pants should have pleated fronts. The pleats allow for a nice full length crease that looks sharp. They are also more comfortable when sitting and they don’t get those nasty wrinkles in the front from sitting like flat fronts do. The pants should have a cuffed bottom. The cuff adds weight which makes the pants drape properly.

Belts should match shoes should match leather watchbands.

Get cedar shoe trees for all of your shoes, including your sneakers. They triple the life of the shoe and keep them looking new for a long time by keeping them in proper shape and absorbing moisture. Oh, no loafers for dress. They are called loafers because they are casual shoes.

Shirt sleeves should extend 1/2 below the jacket sleeves. That extra bit of color poking out there makes a HUGE difference in the overall look. It takes it from nice to sharp.

Not sure where to start? Get a dark charcoal wool suit in a year round weight in a classic cut with partly lined pants. This is the single most versatile suit you can own. From weddings to funerals to interviews to fancy dinners it covers them all in style. Add a nice white shirt with drop point collar, black leather cap toed oxford or wingtip shoes, black belt, black dress socks (black cotton crew socks are not dress socks) and tie with a subdued pattern in deep tones with some red in the pattern. You now have a classic do it all dress outfit that will look great for any occasion requiring a suit. Because it is all classic items as long as it fits you can wear it because it will never be out of style.

Add a black and white houndstooth two button sport coat and a pair of black pants (like I described above) and with the stuff you bought to go with the suit you now have an outfit that can go from borderline casual to dressy and in-between by adding or subtracting the tie and jacket.

Yes, it’s that easy.