You can't fail if you dress well but simply. There is a certain elegance to a person who takes care to pay attention to the minute detail of the footwear they put on when stepping out of their homes to head either to a function or the office.
Dress boots, they are those short leather boots that are typically of ankle length. They became popular a few centuries back, when people would use them to compliment evening formal-wear. Particular in this regard were men.
Technology had a direct effect on the popularity of these type of boots. The arrival of automobiles to the mass markets led to the decline of need for riding boots which were then used as formal-wear. This made the more convenient and lighter dress boots to be used much more frequently.
With all the modern buildings and improved means of transportation there has been a rise of more elegant designs of the dress boot.
The dress boot comes in two main forms; the outdoor boot and the formal boot.
As with the name the formal boot is usually worn for indoor activities like going to watch a play, a formal party or dinner with your better half, family or friends. They have a soft upper made of canvas or suede. They are quite expensive relative to the other boots and have a conservative yet elegant feel. They are worn with suits or any other kind of formal-wear. A great example of this boot is the Oxford boots of the Balmoral cut. The oxfords are very versatile and can be worn with either a tux or a suit.
The difference between the outdoor boot and the formal boot in terms of make is minimal. Outdoor boots are however made with practicality and harsher conditions in mind. They have stronger leather used on their uppers and at times have cordovan used to supplement them. They are mostly brown. The most prominent example are the brogues. They were designed for wearing in the countryside.
You will look awesome when you wear them with jeans on a day out at the park or when on a picnic with your friends or partner.
Essential to dress boots as is with any other kind of shoes is to match them well with your attire. Be it evening attire or daytime.