In all of my years of teaching and mentoring artists perhaps one of the most common things painters mention they want to learn or develop is the ability to be more loose or 'painterly'. Many certainly admire the ability to say much with little, to suggest, and to have the casual and fluid technique that allows the skilled painter to make complex elements of a painting seem simple and effective without being over worked or stiff looking. Often people will marvel that a painting looks messy and random up close but when you step back it looks fantastic. It is quite a skill indeed.
Monet was a confident painter, and he got even more 'painterly' in his old age as his eyesight was failing and he started painting on larger and larger canvases with bigger and bigger brushes. Indeed, that is often suggested as a way of getting more loose in your painting, use bigger brushes and canvases. You can also step back and squint at your canvas, or maybe borrow your friends prescription glasses to help blur your vision.
This is a close up of Monet's famous 'Waterlilies'' painting.
The only way to be really good at this is to spend a whole lot of time painting. I don't know of any shortcut. Perhaps it is because it is not a goal to be reached or to aim for but rather a side effect of reaching a destination called being a really experienced, good painter. I don't think it is a particularly good thing to focus on or try to accomplish, it happens automatically and naturally when you have been painting for a long time and you have developed your eye to see what is essential and leave the rest, and then with a skillful hand, to improvise and to suggest. It is like the ability of a very good speaker or writer to communicate a complex topic in a simple and concise way - that takes a lot of study and practice. I am reminded of story of the person that asked Michael Jordan how he made his jump shots look so easy, he replied with something like "that is because I do 3000 a day."
Moreover, the product of all that work - the ability to paint with confidence and abandon, flowing and spontaneous - is the antithesis of efforting, of trying to be 'loose'. It's like working hard at trying not to work too hard, or trying to be relaxed. If you are trying, you are not relaxing.
I think the same can be said for finding your personal style, which is another major concern for amateur painters - don't bother trying to find it, just keep painting, it will happen on its own. It too is simply an automatic result of hundreds, or thousands, of hours at the easel.
It is also worth mentioning that this fixation is a relatively recent, or contemporary one, the 'Old Masters' were not concerned about this, they were focused on other goals and interests. Also, there are many modern artists of great skill and talent that create marvelous works of art that are extremely precise, or 'tight', in their execution.
Vasari, the famous biographer of the great artists of the Renaissance, remarked on Titian's work from his later years stating that he had adopted a manner of 'painting with splotches'. Perhaps due to his age and failing eyesight it was speculated.
Titian, self portrait
The 17th century term used to describe this phenomena was 'sprezzatura' which is roughly translated to mean 'looseness' or a casual approach in the handling of the paint. Of his paintings Vasari declared: "They cannot be looked at up close but from a distance they appear perfect" It can certainly be said that Titian's latter style did indeed change the course of the history of painting. He also used his hands and fingers a lot in the latter stages of the painting. I do that a lot too.
Rembrandt started his career with a relatively precise and careful execution but ended his life painting in a 'rough manner' as it was called during his day. A contemporary was quoted as saying 'up close it looked as though the paint had been smeared on with a bricklayer's trowel'. Rembrandt himself declared that the paintings should be viewed from a distance and it is said he would pull people away from getting to close to the painting, claiming the odor would be bothersome,...
Below are two self portraits done many years apart that illustrate how Rembrandt's painting style became more 'loose' in his later life.
Rembrandt - self portrait
Rembrandt, self portrait
Rembrandt, self portrait - detail
Check out that brushwork!
We cannot discuss being painterly without featuring a painting of perhaps the most popular of all the messy painters, below is a close up peek at some of the brushwork in Van Gogh's 'Starry Night'.
We also have a perfect example of how taste and fashion have changed when considering the work of Van Gogh's contemporary, William-Adolphe Bouguereau, (1825 -1905). Although Van Gogh is a household name, and he himself absolutely worshipped and revered him, almost no one has even heard of Bouguereau. Yet, in his day, Bouguereau was the most famous and sought after artist in the Western world and his paintings were selling for $250,000 US at the time. Van Gogh only sold one painting during his life, and it was to his brother! Bouguereau was not concerned about being more 'loose' or 'painterly' with his art, and neither should you, no matter your style or how long you have been at it. Just do the work and the 'true you' will show thru.
Bouguereau, "Le Ravissement de Psyche"
I know there are a number to tips and tricks and teaching techniques to help artists loosen up. When I am asked for tips on how to be more 'painterly', I simply suggest that people ask me again after they have done 200 or 300 paintings.