First of all, I don’t recommend you wear them because they very quickly go in and out of fashion and it’s just not a timeless classic style. If you still want to have a four or five button jacket, simply button the middle buttons, leaving the top and a bottom button undone.
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Most vests are going to have 5 buttons down the front, but if you’re over 6’2″ or so, or have an otherwise longer torso, I think a 6 button front would be a good option for you. This would keep the buttons from “stretching out”, but then again, that can be a style preference.
Vest Buttoning
Similarly to the jacket, when buttoning your vest you should always leave the bottom button undone. Your look will be sleek, and you will be comfortable weather you are sitting or standing without having to make any adjustments.
Buttoning Your Vest
Vest or no vest, buttoning the bottom button will make you look like a rube, plain and simple. If you do have a vest on, the bottom button on the vest ought to remain unbuttoned as well.
For a waistcoat, there’s a similar rule: always leave the bottom button open. It’s fashion gospel for men (women are generally allowed to button the bottom button). Men’s suit designers often even tailor the fabric so suit jackets and waistcoats looks more flattering unbuttoned at the bottom.
How to wear a 3 piece suit? Jacket can be worn buttoned or unbuttoned. The waistcoat must always be worn buttoned all the way up, leaving the bottom button open. In the past the open bottom button prevented the waistcoat from riding-up when on horseback.
Secondly, that there was a time when young dandies would sport two waistcoats at the same time so left the top waistcoat’s bottom button undone so that you could see the one underneath. Thirdly, that it is all to do with comfort while in the saddle and to stop the waistcoat rising up the chest while riding.
The same goes for waistcoats (normally 6 or 7 buttons), where we always leave the bottom undone; it’s often difficult to do up in the first place!
Buttoning rules for two-button suit jackets
The traditional way to button a two-button jacket is to fasten the top button and leave the lower undone. The top button on these jackets should ALWAYS be buttoned when standing.
How do you properly wear a vest?
How to wear the vest. Excluding exceptions, the vest must always be worn over a shirt with a buttoned collar and under a single-breasted jacket or blazer. It should never be worn under a double-breasted jacket: the neck of the jacket, in fact, must be large enough to allow the waistcoat to be visible.
Tuxedo Tips
When buttoned, your top button should always be buttoned and your bottom button should remain unbuttoned. If you’re not wearing cufflinks, you will clasp the buttons on your cuff. Your shirt sleeve should hit your wrist right at the beginning of your hand.
If you still want to have a four or five button jacket, simply button the middle buttons, leaving the top and a bottom button undone. I strongly suggest you do not wear a vest or a waistcoat because those jackets are tailored so there’s not much visible space for it.
As suits became the fashion norm for European gentleman in the late 1800s, the English gentry noticed their king, Edward the VII, wasn’t buttoning his bottom jacket button. Why not? Because he was too portly to wear suit jackets buttoned at the bottom.
As we’ve noted before, regardless of how many buttons there are, when wearing a double-breasted suit jacket, it’s important to leave the bottom exterior button unfastened, just as you would with a single breasted suit.
The two-button jacket should never have both buttons fastened. The three-button suit comes with a simple rule: “sometimes, always, never.” It means you should sometimes fasten the top button (if you feel like it), always fasten the middle button, and never button the third.
A 3 button suit looks the best on tall men as their body type is ideal for this type of suit. The buttons of this suit type come up to your chest, which may not look good on short height men. Besides, the 3 button suits are also popular for the comfort it offers.
Given that the primary purpose of an overcoat is to keep you warm and dry, it is perfectly reasonable and acceptable to do up all the buttons to keep out the elements.
Legend goes that Britain’s Edward VII ― a king with several famous appetites ― grew too large for his suit and had to stop using the second button as a result. Not wanting to embarrass him, others followed. The tradition stuck.
Single-Breasted Waistcoat
You don’t want to have to undo a button every time you sit down like you would a jacket. The derivation stems from that same practical reasoning. It is generally believed that the ever-expanding King Edward VII could not sit down on his horse with his bottom button done up.
For those among our readers who do not know what we are speaking of, a three-roll-two jacket is a jacket that features 3 buttons holes and three buttons, but with only the middle button intended to be used. These jackets are usually pressed to roll directly to the middle button.
Always leave the bottom button undone
The golden rule is to leave your bottom button undone. If you fail to do this, get carried away, and button all of the buttons up, than all the time you spent matching your tie, starching your shirt and polishing your shoes will have been a waste.