Most things which work well in life have a sense of coherence about them. This is true of people, but very true of anything visual. Dressing well is the result of the sum of the parts becoming greater than the individual attributes of each component.
To give an easy example, think of any car which is has stood the test of time for its aesthetic appeal, i.e. virtually anything which has come out of the Ferrari/Pininfarina partnership over the decades. What makes these cars work so well is that the lines of every panel, along with the materials used, work together in harmony to produce and overall image which tells a story that is balanced and coherent. The car just looks right.
Now take that same car, let’s say a 458, and put a set of Rolls Royce wheels on it. The visual appeal would instantly fall to pieces. The coherence is broken and all of a sudden competing aesthetics are at play. The sleek, performance focused lines of the Ferrari against the weighty, solid shape of the Rolls’ wheels.
Clothing works in the same way and if an outfit doesn’t seem to work properly, there’s a good chance that some element or elements are fighting each other.
The key points to consider are texture, colour, pattern and fit. Having an outfit work well together requires these things be in harmony. In suiting, there are well established conventions for achieving this, which are familiar to most men who have spent time in professional environments. The classic suit is a smooth wool, mostly without pattern or in subtle patterns, (stripes, checks etc) business shirts follow a similar set of visual clues (subtle lines or checks in twills and other smooth cottons) and ties are silk, with shoes being dark and in polished calf. So for those who have to go to work each day in a suit and have an interest in dressing well, it’s a lot easier to go right, in getting dressed each day.
Where dressing well for the average guy gets harder and seems to break down, is once they stray away from the better known uniform listed above, particularly as you move towards the more casual end of clothing. But it shouldn’t feel anywhere near as hard it seems and that’s where simple guidelines simplify things.
Keeping texture, pattern, fit and colour in mind allows you to pull any outfit together as a coherent whole. As an example of just a small deviation, if you changed the standard suit to a flannel suit, whilst everything else in the outfit could remain the same as you’d wear with a worsted (read: typical) wool suit and still work well together as so little has changed. You can then subtly change the texture of everything else you’re wearing to make the flannel suit work more harmoniously than it would otherwise. For the shirt, change from twill to oxford (same colour, pattern and fit, but slightly more texture to work with the added texture of the flannel). Change the tie to cashmere or wool and the shoes to suede. Nothing else has changed in terms of pattern, colour or fit, but now the entire outfit is in complete harmony with itself. It’s still professional, but now softer thanks to the more muted textures.
By the same token, if you’re wearing a classic worsted wool suit with the other components which compliment this style, mentioned earlier, but the tie won’t seem to work, it’s probably just down to colour being out of sync with the other colours in the outfit or, a pattern which is too strong, or a combination of all those things.
Once we get to jeans, this throws a lot of guys off, particularly at attempts for smart/casual, but the same principles apply in every situation. Put on your jeans, now change the shirt to linen, an oxford weave or something equally relaxed for texture. Change the tie from silk to a knitted cotton or wool/cashmere. Change the jacket to linen, cotton or mohair for warmer weather (see guide on understanding the characteristics of different cloths here), or flannel, cashmere or even tweed for colder weather. Alternatively, forgo the jacket for a wool cardigan (article on how to wear cardigans well is here), which imitates the lines of a jacket, without the formality. And, finally, change the shoes to tassel loafers (minus the socks in warmer weather), monk straps, suede Adelaide’s or something with some brogueing and the outfit will work every time (assuming colour and patterns harmonise, too).
Working to harmonise those four things (texture, pattern, colour and fit) into a coherent whole will make getting dressed every day immeasurably easier and it frees you up to have fun, experiment and find what works for you.