Deciding which tie and pocket square to wear is probably the more challenging task in selecting an ensemble. My ensemble decision follows this sequence:
- Select a suit (or Blazer/Trousers combination)
- Select a shirt
- Select a tie
- Select a pocket square
- Select a shoe
- Select a socks
- Select cuff-links
- Select a watch
- Selecting a suit (or Blazer/Trousers combination)
This is probably the easiest undertaking. The suit is the pivot of the ensemble. Everything else depends on this decision. How do I decide what suit to wear? I don’t think that I follow any set rules. The weather definitely plays an important role (for example, a heavy suit in a hot day is ridiculous; similarly a light linen suit in the thick of winter, etc.), season also plays a role, and the occasion (business, formal, informal, etc). If I have any official evening engagements and I am not planning to return home to change, I prefer to add a darker suit. Similarly, if I have planned for any formal customer engagement during the day, probably I will avoid a linen suit, which is considered less formal.
- Selecting a shirt
Though what shirt to wear depends on the suit, one often has a number of alternatives like color, one color or multicolor, solid or pattern, etc. The easiest thing to do is to wear a white shirt as white goes with any suit color and sometimes it is the best shirt color with a suit. But wearing a white shirt everyday is boring and one needs to spice it up with shirts of other color. The next easy shirt color is solid followed by various types of stripes and lastly checks.
- Selecting a tie
For me, selecting a tie is the most challenging aspect in configuring a harmonious ensemble, even if I am wearing a white shirt where technically any tie goes. The challenge stems from the fact that the tie must be compatible with both the shirt and the suit, but predominantly the shirt (as the shirt was selected because of its compatibility with the suit). The other aspect of the challenge stems from the fact that to avoid monotony, everyday you are also trying a come up with a fresh ensemble—to create something new that is unlike what you have done before, it’s like an artist painting a picture, a musician composing new music, or a chef trying to come up with a new recipe, or a military planner drawing up an invasion plan, or a marketing strategist preparing a product strategy, etc.—it’s all about creativity. Some part of it is based on hard sciences, like color spectrum, color theory, pattern recognition, etc., and the rest is art—just like any other creative endeavor. In my opinion the most difficult undertaking is when you have a check suit (like a glen plaid or windowpane), a patterned shirt (either a stripe or check), patterned tie (polka dots, microdots, etc.) and a check pocket square. Everything can go wrong in these types of ensemble and one is playing on a knife’s edge.
- Selecting a pocket square
The next task is selecting a pocket square. The basic idea is that the more you have the more difficult it is to decide. Selecting a suit is easier because you are likely to have fewer suits than shirts; selecting a shirt is easier than selecting a tie for the same reason. Selecting a pocket square is similar to deciding on a color on a painting and the more skilled you are the better is your selection and the overall composition.
- Selecting a shoe
Not a difficult chore at all because your choice are limited to black or some shades of brown and the choice is often dictated by the color of your trousers.
Black shoes go with almost everything. Brown shoes (any shades of brown) goes with many colors except with a black suit. With a navy suit I would probably wear brown, cordovan, and black in that priority. My preference, however, with navy suits is to wear brown or cordovan. Occasionally, I may wear black shoes.
With gray suits, I would wear black (if its dark gray or charcoal gray and particularly at night), with light gray I would wear brown, cordovan, or black depending on my mood.
With a brown suit the choices are limited—its either brown or cordovan, never black.
With a tan suit, anything goes—brown, cordovan, or black.
With a olive suit, I would probably wear brown (a reddish brown looks excellent) or cordovan, seldom black.
And lastly, with a black suit—the shoes are always black.
With a formal suit, nine out of ten times, I would be wearing a lace-up (oxford or derby shoes). With linen and other semi-formal suits I would also add monks. With blazer/trousers lace-ups, monks, and slip-on.
- Selecting socks
It is a relatively simple task. I would always match the socks color with the color of the trousers. If I don’t have the exact shade, I would select one that is darker than the trousers and never one that is of a lighter shade.
- Selecting cuff-links
Not much complicated. I don’t like cuff-links with much ornamentation. I prefer simple elegant cufflinks. Often, but not always, I would match the cufflinks color (silver of gold) with other accessories I am wearing like watch, belt buckles, etc.
- Selecting a watch
I would tend to wear a watch that would be compatible with other accessories. I prefer minimalist design in watches.
- Selecting Belt or Suspenders
With a suit my preference is wearing suspenders. However, occasionally I would also wear belts. If I am wearing a belt, its color must match the color of the shoes.