Contrary to popular belief, men's dress clothes should always be comfortable. If they are not, it is the fault of the clothes' fit, and not of their nature. Suffering for beauty's sake does not do a man any good, eithe; if the fit of a garment makes its wearer uncomfortable, he will look it. Indeed, a man looks his best when his clothes fit so well he barely notices them. On the other hand, if they are too tight, they will be pulling and choking at every turn; too loose, and a man looks like he has had to borrow some clean clothes from his older brother as he struggles to keep them out of the way. A man's clothes send a message to the world about him, and if they fit him well, he will always make a good impression.
Most men today wear poorly-fitting clothes, and it is not hard to see why. The goods sold in stores are cut to fit as many people as possible, and that means big. At the same time, the fashion-industrial complex creates new so-called styles by bending or breaking the time-honored traditions in menswear; thus it is that designers and commentators may debate whether baggy or fitted pants are 'in' this season while neither look as good as the timeless middle-ground. A good deal of men still rely on women to hold their hands through shopping trips, but since the prerogatives of fit are altogether different for women's clothing, the results are often sorry. Finally, when you are buying a garment, the retailer has little incentive to tailor it properly, since nobody seeks out a mall store because he's heard they do great alterations. Thus as in so many things, it falls to each man to take responsibility for the fit of his own clothes, and not to be swayed by the prolific selection of poor choices or the dubious influence of models, salesmen, and the opposite sex.
The first step in acquiring properly fitting clothes is knowing what proper fit looks like. In general, clothes should be comfortable, but not loose. Pants should be worn at the natural waist, near the navel. Young people with flat stomachs may choose to wear them lower, as has been the style for a decade or so, but they gain little in doing so. The man with a belly, on the other hand, looks much better with high-rise trousers draping from his middle than with his stomach spilling over a low-rise waistband. The bottoms should touch your shoes' uppers, but of course must not touch the ground. The most standard length brushes the top edge of the sole at the back, for a slight break in the front. Shorter pant legs, just brushing the tops of the shoes, can look better on the shorter man, and also allow one to show off his socks and shoes should he care to do so. Additionally, men under 5'9" do better without cuffs on their trousers, but should they want them they should be in proportion to their stature, 1¼"-1½", while men over six feet take cuffs 1¾"-2".
If a jacket, meanwhile, is to have any hope of looking good, it must fit correctly in the chest and shoulders. When you stand with your jacket buttoned and arms hanging loosely at your sides, the jacket's lapels should lie flat against the front panels, the buttons should hang close to or rest lightly on your stomach, and your biceps should just barely break the drape of sleeve from shoulder. Of the many other factors involved in fitting a jacket, the chest and shoulders are the most important and the hardest to alter. Your shirt should always be tighter than your jacket, lest you end up with clumps of fabric which have no place to go. The cuffs should protrude ¼"-½" from the jacket's sleeves when you stand with arms hanging; the collar should cover ½"-1" of your neck above the jacket collar. There is of course much more to say about the fit of these and other garments; these points are intended merely to illustrate the basic idea of fit.
Let me note here that buying clothes that fit means buying clothes that fit your body, as it is, and not measuring them to an idealized vision you have of yourself. Many men, when getting measured for a suit, will stick out their chests and stretch their spines, striving toward some idealized masculine figure. Unless this is how you stand normally, though, this is not how you should be measured. You can round your height up an inch on your driver's license, but you only hurt yourself by embellishing for your tailor. Similarly, in certain cultures where weight loss is an obsession, some men succumb to the folly of 'buying skinny.' That is, they buy clothes one size too small, anticipating a perfect fit when they lose weight. This is a dangerous proposition, both for one's bank account and one's self-esteem, and it is also misguided. Almost any shirt, sweater, or jacket that fits you well will still fit well if you gain or lose ten pounds. Pants are the most sensitive, but even these will withstand small fluctuations. When your waistline does shrink or grow by a half inch or more, they can easily be altered, often several inches in either direction. Unless you are still going through puberty, you have nothing to gain by selecting clothes which do not fit your body as it is today.
It is a wonderful feeling to don garments that have been tailored to fit you perfectly. One feels light and comfortable as one's clothes seem to float around the body, neither heavy nor tight anywhere but rather resting evenly throughout. Clearly, getting such clothes retail is nearly impossible, or more men would do it. While there may be a suit that fits you perfectly somewhere, your odds of finding it are slim. Even to build a small wardrobe of decently fitting garments, a man must spend many hours searching through racks and trying things on. Fortunately, though, custom made tailored clothing can now be had for less than most designer brands. Once he knows his dimensions and has a trusted source, it is simple for a man to acquire professional, formal, and casual clothes alike that fit just right, and he will look grand in all of them
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