The legend has it, that when King Edward VII of England started leaving the last button of his waistcoat open to be more comfortable, the aristocrats of the era followed this trend. Always leaving the last button undone maybe the least useful thing to know about how to wear a vest to impress. But it is a fun fact and additionally it is kind of a secret signal among men who really know how to dress to the nines.
Vests are a very versatile piece of clothing and they can fit practically any style. No matter what type of vest you choose to wear, make sure that it fits you well. What this means, is that your waistcoat does actually coat your waist and your belt and shirt do not show. Make sure that your shirt is neatly tucked in your pants and does not create a puffy waistline underneath your vest. If you find the vest of your dreams and it runs a little too big, a seamstress will be able to adjust it to your size.
There is a waistcoat for every occasion. Leather vests are appropriate for everyday casual outfits and they can be worn with all sorts of t-shirts and preferably fitted jeans. Go for a more loosely fitting shirt and leave your vest unbuttoned for a relaxed yet unique style. If you want to go at the other end of the fashion spectrum, you can go for a three-piece suit or tuxedo with a vest. Super classy and you can experiment a bit. It’s not just all black or gray as you might think. You can keep the two basic pieces in one dark color and then choose a vest in dark jewel tones, such as burgundy red or emerald green. Your tie or bow tie can be matching your vest or suit. And keep the shirt a neutral color, such as white.
If you want to wear your vest with jeans but you are not into leather, then you can go for a gray or brown herringbone vest and combine it with either plain t-shirts or even plaid shirts with the sleeves rolled up, for a more laid-back look. And here is a slimming trick for you: keep your vest in a dark tone and wear a brighter shirt. This way your torso and waist look narrower and the attention goes to your arms, that are naturally slimmer.
If you want to upgrade your office wear and give it a twist, you can invest in a pants-vest suit. A glen plaid is a great print to go for in this case. It will save you from the waiter look of black vest-black pants-white shirt and it is a unusual in a good way. You can still go for the black vest-white shirt, as long as you have a tie that differs in shade.
And now three things that you should not wear when it comes to vests: sweater vests with buttons if you are under 50. They just make you look old. Also, vests without a shirt. Except if you are a stripper or work in a circus. Not acceptable. And please, do not wear those puffy, snow-gear athletic vests. You are allowed to do that only while snowboarding. And it better be black.