Many of you choose clothes for men in your lives, either by default, or because you have annexed this territory in a war of conquest. In either case, you are now in charge of dressing a man for the most important occasions of his life.
With great power, comes great responsibility. First you must understand that dressing a man is different from dressing a woman. Many well-dressed and well-meaning ladies fail by not understanding this point. But despair not. These next few paragraphs are meant to help.
Because I have a generous heart, I am going to suppose that you want your man to look like a well-dressed gentleman, rather than your plaything. Unless your goal is to display your ownership of your companion, as a dog pissing on a tree, you don’t want your man looking like he was dressed by a woman. Take this as your guiding principle. Even though you may privately savor the knowledge that but not for your efforts, your date would take you to a black tie party wearing tennis shoes and a ski jacket, let the other guests believe that you are being escorted by an adult capable of dressing himself.
The good news is that it’s easy. All you need is a well-fitting dark (but not black) suit, well-shined black shoes, a clean, ironed, white shirt, and a conservative necktie. If it’s an evening occasion, it can be this one. If it’s during the day, it can be this one. Stuff a white linen handkerchief in the breast pocket of the jacket if you like. That’s all there is to it. A man can wear this exact outfit every single time he is called upon to wear a suit and tie and be very well dressed. Notice the pictures above of leading men (Marcello Mastroianni with Anita Ekberg in La Dolce Vita, Cary Grant with Audrey Hepburn in Charade) with their costars. They’re wearing simple clothing that fits. These pictures are 50 years old yet they still look great today.
The hard part of the job is resisting every inclination you have to make it more difficult. You will have a nagging sense that this outfit seems boring or lazy. You reflect on the wide variety of choices you have in your clothing, both in dress styling and colors. You might think of how much you enjoy wearing bright colors that complement the bright colors you have (regrettably, in my opinion, but there it is) painted on your face or perhaps even nails. You feel the dread of wearing something too similar to another woman, or someone recognizing that you have repeated an outfit.
None of this carries over to male style. Traditional male outfits - the tuxedo/dinner suit, white tie and tails, and morning dress, each described ably here - offer very little room for deviation. Save the possibility of a colorful necktie with morning dress, black, white, grey, and dark blue are the only colors on the palette. These are the most flattering outfits a man can wear. They can be worn every day and every evening for which their level of formality is appropriate. The modern suit and tie is an attempt to capture some of their dignity with less bother and discomfort.
Notice that in my description of the well dressed man’s costume I made no mention of what his date might be wearing. Just as a man should not match items within his own outfit (the tie-and-pocket-square sets you see on display in department stores are sold to women buying for men) he should not match items in his date’s outfit. Remember our first rule of a woman dressing her man: leave no fingerprints. When I see a man in a tie that matches his date’s dress, I know that she has thrust it upon him. I feel sorry for him and wonder if he has to ask for permission to go to the bathroom. It’s also a signal that these items were bought (to say nothing of the possibility that they were rented) specifically for this occasion, which again is something that our well-dressed classic gentleman with the always-ready dark suit and conservative tie would never confess to. All this is fine for 16-year-olds playing dress-up for the first time at prom, but now that you’re an adult, you and your date should dress like one. Adults don’t wear matching outfits unless they work as a professional athlete, waiter, or boy band member.
All it takes is a one-time investment of the few hours required to acquire a well-fitting suit, and a periodic shoe shine. Other than that, your job is easy, if you’ll just let it be.
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