In “Anna Karenina”, Tolstoy wrote “All happy families resemble one another, but each unhappy family is unhappy in its own way.” The same logic can be applied to well and poorly dressed men. All well-dressed men, have one thing in common: their clothes fit well. Wearing simple, well-fitting clothes can mark the difference between dashing and schlubby.
It should come as no surprise that mass-produced garments are intended to fit as many different bodies as possible. The problem lies in the fact that you have one, very specific body. It isn't small, medium, large or xxxl, it's you-sized. Even dress-shirts, with their more specific neck and sleeve-length size don't account for different chest, waist and biceps size. So what's a man to do, if he can't find clothes that fit properly, you ask? Make them fit.
In a perfect world, we would all have custom clothes tailored to our bodies. Unfortunate that is not a financial reality for most people (although affordable internet-based made-to-measure services like Modern Tailor and Cotton Work are becoming increasingly more common). No, the difference between having an ill-fitting or razor-sharp wardrobe can be as simple as a few trips to the tailor.
Many neighborhoods have dedicated tailor shops, and most dry cleaners offer some basic tailoring services. We all know that tailors can easily hem out unfinished suit pants or take in that baggy sport coat, but they can just as easily slim a shirt or taper pants-legs for as little as $10. If you're wary of diving off the deep end, start with one shirt.
Basic alterations are a quick and easy step toward improving one's wardrobe, and requires very little up-front investment. Whether you're a certified clothes horse, or just a guy looking to start dressing better, you first trip should be to the tailor, not the mall. A man in perfectly fitting khakis and a polo is better dressed than one in an ill-fitting, misshapen $2000 suit.