There were a number of influential experiences in my life that instilled a set of basic rules regarding how to put together a polished, well-dressed look:
Living and working in Europe. Europe is a place where tailored Italian dress shirts are the norm, quality over quantity is an observed rule of behavior, the full spectrum of colors for clothing are embraced, and fabric textures are truly appreciated.
Being the son of a Lutheran minister. I grew up around the church and the formalities of German-Scandinavian church culture, which tends to stress formal dress, restrained behavior, and respect for traditional conventions. So part of my dress style is also a reflection of my respect for formal traditions and conservative, classic appearances.
Being a Tux rep in high school. There is nothing like wearing a tuxedo as a teenager once a month to school to get one acclimated and attuned to getting dressed up. Need I say more?
Rule 1: Choose the Right Colors
Know which colors look good on you as opposed to picking colors based on trends or to just to fit in. If you do not have a good color sense, then please seek out a woman or women with good taste to help you out. Really.
Unfortunately many guys are not good in this way. They just pick out a gray suit, match a tie to the suit, and they call it good, as opposed to picking colors based on what fits them first and foremost. Personally, I like deep, rich colors like maroon, forest greens, deep or bright blues, and tend to stay away from the paler shades. But, I know this about myself.
Rule 2: Accessorize
Just as for women, accessories make the outfit. Pay attention to the details, such as quality of tie, type of tie knot, belt, style of shoes, shine and polish of shoes, type of overcoat, vest, pressed shirt. Take care of the accessories, and the accessories will take care of you.
Rule 3: Respect Your Dress Clothes
Take care of your clothes. Use quality hangers and allow your clothes some space in the closet. Are you using cheap hangers in a cramped space? Please, don’t. Treat your clothes with a respectful attitude, and they will serve you well for years to come.
When traveling, this is even more the case. Keeping your clothes in a dry cleaning bag when they are in a garment bag or suitcase will help protect your clothes. Then, unpack and hang up your clothes as soon as possible to avoid a sloppy or wrinkled look.
Rule 4: Fit Matters
How your clothes fit does matter. I learned this from European businessmen and U.S. corporate executives. Be mindful of certain areas for a good fit. Collar size on a dress shirt is critical. Avoid the oversized collar, which lends a sloppy appearance. Other key areas are the fit of the shoulders and the length of both shirt and jacket sleeves.
For dress pants, how high or low someone wears his pants makes a tremendous difference. Too low looks sloppy, and too high looks nerdy. With dress pants, the looseness or tightness of the fit should conform to the looseness or snugness of the jacket fit. If you are mismatched, like wearing tight pants and a loose jacket, then it had better be on purpose; otherwise it throws off the look.
Rule 5: Be Comfortable
It’s important that you are comfortable being dressed up. This is easier said than done, of course. Similar to the last point, if you’re not comfortable with your clothes and who you are in such clothes, then even if you have the nicest dress clothes, a sense of “style” will be lacking. Personally, I love “dressing up” and look forward to the opportunities to do so.
Rule 6: Keep a Dignified Appearance
How you carry yourself affects your style. If you stand, walk, and carry yourself in your dress clothes just as you would if you were in shorts, T-shirt, and flip-flops, then it will detract from your overall appearance. Carry yourself with dignity. Your appearance will change and your clothes will thank you.
Rule 7: Choose to Look Good
You have to want to look nice. I notice that many guys do not care much about how they look and are just wearing a suit or nice clothes because “they should.” If that’s the case, then the other points don’t make much difference. Make the sincere decision to look nice, and everything else will follow.