The wearing of clothing accessories is perhaps best viewed metaphorically in culinary terms. Think of your clothes as the ingredients of a good meal, their quality provides the basis for an excellent dish. The cooking skills required to prepare the meal are akin to your knowledge, skill and ability to match the right clothes to you and to each other. Finally, the seasonings you use (e.g. salt/pepper, herbs, spices etc.) to elevate an ordinary plate to one of great delight are the clothing accessories you use to lift a presentable man to one of debonair style. As one wouldn’t normally add garlic to fish but would add it to venison, there are some basic rules for clothing accessories:

Unless your clothes fit and match your physical attributes (size, shape, coloring etc.) any accessories you use will, at most, be muted in their effect. If you are wearing a sport jacket several sizes too big, adding a pocket square is only likely to increase the impression you are wearing a clown’s costume.

Almost all clothing accessories have a utilitarian function, and your items should perform this given function first and foremost. Many of the individual “rules” for an accessory are grounded in this practical functioning e.g. not using a tie bar when wearing a vest (waistcoat), because the vest already keeps the tie in place making the tie bar superfluous. Also take into account your own personal considerations e.g. if you rarely wear a tie you may only need one or two tie bars.

Accessories, like your clothes, should be of a timeless and classic style. The main purpose of this is for longevity i.e. not buying fashionable items today, you won’t be able to use tomorrow. Always have in mind the possibility of handing down these items on to your relatives! The other reason for simple elegance is understated subtlety i.e. no outlandish or gaudy items. A walking stick with a skull head is useful for a Halloween/Pirate costume or perhaps just looking Gothic and “mean” but it is not an everlasting image of style.

Pairing a t-shirt from Walmart with a Rolex wristwatch looks odd and out of balance. If you are carrying out maintenance or repair work around the house, pairing the aforementioned t-shirt with a $10 - $20 digital watch is fine. Whilst enjoying drinks at sunset on a balmy evening, a cotton/linen/silk short-sleeved shirt provides a better match with the Rolex.

Accessories give out a message, with the level of contrast (stark = bolder) and the amount of accessories (more = higher authority) determining how much or how bold the message is you wish to portray. Just as male animals in nature often have colorful and/or (practical) ornate aspects to them (e.g. horns on bulls, long feathers with vibrant colors on peacocks etc.) then the accessories you use are giving out signals to other people (hence the term “peacocking” to describe how some men are dressed). Often this is associated with attracting a “mate” (e.g. appearing affluent) but this is not the only message e.g. wearing cufflinks, tie bar, pocket square etc. when in a suit can be seen as “badges of authority”. How much and how bold is down to your personal choice, but remember to dress according to the occasion e.g. be subtle in formal settings.

Besides adding accent to your ensemble, accessories can also be used to relay a message: American flag cufflinks on George Washington’s birthday; a tie bar with your family, club or University crest on it; a boutonniere the color of your birthstone worn on your birthday; a scarf in your sports team colors; a pink pocket square during October for breast cancer awareness month etc. The list of options here is only limited by your own imagination, and with thought and care can become real conversational pieces. Perhaps the best choice of all is the use of vintage items handed down within your own family from relatives e.g. grandfather, father, uncles, etc.  

As with most things, subtlety is better and less is more! The aim is to be noticed but not to be starred at. Clothes and accessories should be used to externally signal who you are, with the overall image matching your inner qualities. Your character is much more important than how you look but use how you look to reflect your true self.