Whether you are willing to admit it or not, these days it is essential for a man to have fashion sense. Before you get too disgusted (or discouraged) thinking about it, let me clue you in. It only takes following two simple rules to achieve a pulled-together, “Mad Men”-ish look.
These rules have been around forever, so it seems everyone should know them by now. However, after working at a men’s suit shop, I learned that is simply not the case. A lot of men (and an even scarier number of the women in their life) don’t know these two rules. Follow them and you’ll avoid making any blatantly obvious fashion faux paus (you know, the equivalent of asking your buddy if the fourth quarter of the hockey game has started yet).
1. Buttons: Sometimes, Always and Never
There are rules to buttoning your suit or sport coat (and they also apply to a tuxedo rental). To most men, it seems logical that if there is a button, you should button it. Unfortunately, fashion is not always logical.
If you have a two-button suit coat or sport jacket, remember this rule: always, never. Simply start at the top button and count down. Always button the top button, never button the bottom one. Sure, it is just a seemingly silly fashion rule (and no, I don’t know if a woman made this rule up, although it does sound like something we would do), but it actually does make a difference. The coat always lies better when worn in this manner. Even if you have abs rivaling Ryan Reynolds, the coat will look sleeker if it drapes at the bottom. This is especially true if you have a little more padding around the middle.
If you have a three button coat, the rule changes slightly: sometimes, always, never. This gives you a little flexibility. While you will always button the middle button and never button the bottom one (yes, never, even if it is a formal event), you can make a choice about the top button. Before you make that decision, know that buttoning the top button really drives home the intended look of a three-button suit–sleek. A man in a three-button suit is a sleek look that is rarely rivaled.
Keep in mind, the never rule applies to a vest, too. If you’re donning a vest for a wedding, or rocking a vest for a dressy casual look, always leave the bottom button undone (regardless of what your girlfriend says, leave it undone).
2. Match Your Shoes to Your Belt
Men tend to get overwhelmed with worry about matching. Trends now are diverse, so matching your shirt and tie is easier than ever. This means there is only one hard-fast matching rule you must abide: always match your shoes to your belt. For the most part, the color of belt and shoes is fairly inconsequential, as long as they are the same.
Why These Rules Matter
A well-dressed man exudes confidence. That confidence is always noticed in two key areas of life: professionally and romantically. The age-old mantras “dress for success” and “dress to impress” are always applicable to prospective employers, your boss and clients (and who doesn’t want to make a good impression there?). The same goes for women. You’ll be hard-pressed to find a woman who can resist a well-dressed man.
You may not be a “Mad Man” in training, or even care to be, but you can certainly fake it with the best of them when you remember “sometimes, always, never” and match your belt to your shoes.








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Great points. Though find a good tailor is key so that you don’t look like you’re wearing a trash bag for a suit.
VERY good point, Mike! A good tailor is imperative and will make sure your suit fits you just as it should.